Best Airbnb & VRBO Vacation Rentals in the Berkshires (March 2023) | Budget your trip (2023)

Family friendly cabin rentals and holiday homes in Stockbridge, Lenox, Great Barrington, Williamstown and more

Family trips to the Berkshiresare an integral part of Massachusetts life. The area offers a beautiful setting for a family vacation, with AirBnB cabin rentals giving groups of all sizes the opportunity to experience the best of the Berkshires.

Small historic western Massachusetts towns like Stockbridge, Williamstown and Lenox have many beautiful mountain homes that allow visitors to enjoy the best of the Berkshires - from hikes to festivals and farms to table restaurants, Berkshire County has it all.

For families looking to make the most of their visit, a vacation rental on Airbnb or VRBO is the best option. Many rental homes and cabins offer relaxing outdoor areas with fire pits, hammocks, and some even swimming pools.

Below are some of the best vacation homes in the Berkshires.

Pair of chickens: Lenox|Stockbridge|Pittsfield|Grand Barrington|Williamstown|Lee|Nord-Adams

Lenovo Airbnb and VRBO

Lenox is a popular destination for visitors to the Berkshires. It's a small town set against the backdrop of the beautiful southern part of the Berkshires. It has a beautiful downtown that is perfect for walking. Historic New England architecture gives this village character. There are a number of excellent local restaurants, as well as spas and arts venues. The city is also famous for its Tanglewood Music Festival, which features the Boston Symphony Orchestra.

Children will love the hiking trails in the area. There are many trails that have hills and are not too strenuous for small legs. Horse lovers will enjoy a horseback ride, which is the perfect way to experience the Berkshires.

This town has a number of excellent family vacation rentals. Below are some of our favorites in and around Lenox.

"Dorfblick"

Lenox, Massachusetts

The list goes on with this beautiful home in Lenox, so be sure to add this to your favorites list. The location of this apartment is perfect as it is in Lenox. This location is minutes away from Zinc and Haven. If you just want to eat out, you can use the fully equipped kitchen to prepare all your meals. Everyone can also spread out in the living room, dining room and on the balcony. With room for the whole group, this is a great holiday home for the whole family. Each room offers a comfortable place to relax. One bedroom has a king bed and several other rooms have queen beds. Board games, BBQ and parking are also on the list of amenities. Check out the photos!

Heart of Lenox, walk to town

Lenox, Massachusetts

Sleeping 4 people this is a 2 bedroom house perfect for a holiday rental in Lenox in the Berkshires. It is perfectly located in Lenox so you can explore the city on foot or easily drive to the other nearby towns. As for the interior design, this house offers all the comfort you need. The microwave and dishwasher in the fully equipped kitchen allow you to prepare all your meals if you wish. Each room offers a comfortable place to relax. Each has its own king-size bed, perfect for couples traveling together. And with a living room, dining room and balcony, everyone can spread out and relax. Smaller families and couples love this place as it is the right size and price.

Lenox Lake House in Berkshire

Berkshire County, Massachusetts

This lakefront home is a great place to stay during your time in the Berkshires. Relax in the water before enjoying local food and shopping at the nearby boutiques and cafes. With 4 bedrooms and 2 bathrooms there is plenty of room for up to 10 people here, so add it to your wish list. This large home is perfect for a large family or group of friends. Prepare your meals in the kitchen, which is equipped with modern appliances such as a microwave, oven, fridge and dishwasher. There is also the dining area which offers guests more space. The 4 bedrooms are neatly arranged so everyone can sleep comfortably. With a king-size bed in the master bedroom and queen-size beds in the other bedrooms, everyone will be comfortable. Additional amenities include parking, garage and BBQ. Staying here will make your trip to Berkshire County fun and convenient. Are you ready for a fun-filled vacation at Lake House? This is the place!

Cozy Berkshires cottage

Stockbridge, Massachusetts

This cabin is a popular option because it's right on the lake shore. It has 2 bedrooms and 2 bathrooms. This cabin is perfect for a large family or a group of friends. Both bedrooms are beautifully furnished. There is a king bed in one bedroom and a queen bed in the other. The kitchen is practical, well equipped and of course has everything you need to prepare your own meals. In this apartment you will also find a barbecue, parking and internet. The main attraction here is of course the lake, and you will have fun on the water and relax while admiring the breathtaking views.

the playhouse

Berkshire County, Massachusetts

This is a massive 6 bedroom, 5 bathroom place that is spacious and beautiful. It can accommodate up to 20 people. This large property is perfect for group events, family reunions and larger gatherings. The 6 bedrooms are well laid out so everyone can sleep comfortably. And with multiple bedrooms with queen beds, everyone has their own space. The fully equipped kitchen has everything you need such as a microwave, dishwasher, stove and oven. The huge open layout of this home means everyone can have fun while participating in all the activities (and you can keep an eye on the kids).

The hosts obviously work hard to make visitors happy as this vacation rental has earned an excellent rating with many positive reviews. The Tanglewood Music Center, Norman Rockwell Museum, National Sanctuary of Divine Mercy, Lee Prime Outlets, Salmon Run Fish House and Chez Nous are within 5 miles of this location. It's hard to find a place like this so check before you book.

3 Bedroom Renovated in Lenox

Lenox, Massachusetts

For anyone looking for a fun vacation in Lenox, this 3 bedroom, 2 bath home is a great vacation home as it sleeps 6 people. With space for the whole group and a huge garden, this is a great holiday home for the whole family. The fully equipped kitchen has everything you need such as a microwave, dishwasher, stove and oven. All rooms are well furnished. There is a king size bed in the master bedroom. There is also the living room and dining area, which offers guests more space. And you'll love relaxing on the back patio with outdoor seating area while the kids play in the garden. Barbecue, parking and internet are also on the list of amenities. In the area you will find many typical shops. This is a great place to start enjoying your next trip to Lenox and the Berkshires.

Casa Lenox center

Lenox, Massachusetts

Meet the friendly locals and enjoy small town charm at this beautiful home. This Lenox home has an array of comfortable touches and a relaxed vibe. The 3 bedroom, 1 bath condo has a long list of features and sleeps up to 6 guests. There is plenty of space for the whole family or group. All rooms are well furnished. You can eat out or just stay at home and prepare all your meals in the kitchen. You can also spread out on the balcony.

Additional amenities include parking, internet and garage. This is a convenient option for anyone traveling to Lenox. The Tanglewood Music Center and Cranwell Golf Club are also less than 3 miles away.

Staycation in chic, comfortable, contemporary home

Lenox, Massachusetts

Places like this book up quickly. This 3 bedroom house can accommodate up to 8 people. This home is perfect for a large family or group of friends wanting to explore the Berkshires. The 3 bedrooms are neatly arranged so that everyone can sleep comfortably. Two of the bedrooms have queen size beds. Guests enjoy the fully equipped kitchen, which is great for preparing home cooked meals. You'll feel right at home in the living room, which offers even more space to relax. Also on the list for this home is parking and internet. Add this to your Wishlist!

Very private setting but walkable to town

Lenox, Massachusetts

If you are looking for a vacation rental in Lenox, this 3 bedroom, 1 bath home is a great option. This incredible home has everything you could possibly need and style too. There is plenty of space for the whole family or group. All rooms offer everything guests need. Two of the bedrooms have queen size beds which is great for everyone. Not far away you will find the Tanglewood Music Center and the Norman Rockwell Museum.

heart of lenox

Lenox, Massachusetts

Relax here in a small town. A popular rental in Lenox, this spacious 2 bedroom, 1 bathroom apartment sleeps up to 6 people. This is a great option for a family as there is room for everyone. Check out the photos! The kitchen is well equipped with fridge and dishwasher. Both bedrooms offer everything guests could need. There is a king bed in one bedroom and a queen bed in the other.

Modern and comfortable classic house

Lenox, Massachusetts

Meet the friendly locals and enjoy small town charm at this beautiful home in Lenox. This is a large room and would be perfect for a large family or multiple families holidaying together. The 4 bedroom, 2 bath home is in a great location. Less than 5 miles away you will find the Tanglewood Music Center, Lee Prime Outlets, Bousquet Ski Area and Cranwell Golf Club. Places like this book up quickly.

Stockbridge Airbnb und VRBO

Stockbridge is another charming town in a central part of the Berkshires. The town center is slightly smaller than Lenox and there are only a handful of restaurants to choose from, but there are beautiful hiking trails along the Housatonic River. This city is known for its cultural attractions. Be sure to check theBerkshire Theater Company, which is known for its plays and musicals. Children and adults alike will enjoy a visit to the Norman Rockwell Museum, where you can see a number of famous works. As for food, a trip to Stockbridge is not complete without a meal at Lion's Den. They offer classic New England fare that kids and adults alike will love.

There's no shortage of outdoor activities near Stockbridge either. Hiking and skiing are popular in the area.

There are several large houses for rent in the Stockbridge area. These plots usually occupy a large area and provide plenty of space for families to gather. Below are some of our favorites.

Spectacular scenery on the private lake

Berkshire County, Massachusetts

Wow! Located on its own private lake, this beautiful cottage offers a host of comfortable touches and a relaxing atmosphere. The 4 bedroom, 3 bathroom apartment has a long list of features and sleeps up to 10 people. This property would be an amazing option for a family or group with all their extra space. The 4 bedrooms are neatly arranged so everyone can sleep comfortably. There is a king bed in one bedroom and a queen bed in another. Children will also enjoy the bunk beds in one of the bedrooms. The kitchen is well equipped with a microwave and dishwasher. You'll feel right at home in the living and dining areas, which offer even more space to relax.

Games, BBQ, parking, internet and table tennis are also included. This is a good find for anyone heading to the Berkshires. Please do not hesitate to bring your pets with you to this accommodation. The Tanglewood Music Center and the Norman Rockwell Museum are also close by thanks to our convenient location.

Modern country home in the heart of the Berkshires

Stockbridge, Massachusetts

This spacious 3 bedroom, 1 bathroom home is amazing and sleeps up to 8 people. If you are looking for comfort and convenience this is a great home. Wake up in the morning with your coffee on the veranda or relax with a glass of wine in the evening. This is a family friendly place with enough space for everyone. Or it could be good for a group of friends.

You can eat out or just stay at home and prepare all your meals in the kitchen. You'll feel right at home in the living and dining room, which offers even more space to relax. The 3 bedrooms are neatly arranged so that everyone can sleep comfortably. There is a king bed in one bedroom and a queen bed in another.

And more amenities can be found here, such as games, barbecue, parking, internet and garage. Pets are also welcome.

Victorian in town

Stockbridge, Massachusetts

This Victorian home is a popular choice in Stockbridge as it has 12 bedrooms and 6 bathrooms. Many people enjoy staying in this large space for family gatherings or group gatherings. In the rooms you will find beautiful furniture. Since two of the bedrooms have king-size beds, everyone can sleep comfortably. Bunk beds in the other bedroom are perfect for children. The fully fitted kitchen is well equipped and practical and includes a microwave and dishwasher. Enjoy meals or relax in the living room, dining room and on the balcony of this accommodation.

Included in this property are games, BBQ, parking, internet and bikes. As an added bonus, your pets are also welcome.

You are in a great location near the Norman Rockwell Museum, the National Shrine of the Divine Mercy, Once Upon a Table and the Main Street Cafe. This incredible home has everything you could possibly need and style too.

Quiet 3 bedroom Stockbridge house

Stockbridge, Massachusetts

There is plenty of space for the whole family or group. The 3 bedroom, 1 bath home is in a great location. The Tanglewood Music Center, the Norman Rockwell Museum and the National Shrine of the Divine Mercy are also nearby. This is a good find for anyone heading to Stockbridge. Prepare your meals in the kitchen as there is a microwave and an oven. In the rooms you will find beautiful furniture. The master bedroom has a king size bed. In this place you also have parking, internet and garage.

rabbit race

Stockbridge, Massachusetts

A popular holiday rental in Stockbridge, this spacious 3 bedroom, 2 bathroom home sleeps up to 7 people. With room for the whole group, this is a great holiday home for the whole family. This incredible home has everything you could possibly need and style too.

There is a fully equipped kitchen for those who enjoy cooking. There's even more lounging space in the living room, dining room, and lanai. The 3 bedrooms are neatly arranged so that everyone can sleep comfortably. There is a king bed in one bedroom and a queen bed in another. Families and groups will appreciate the game room. Fire pit, grill, parking and internet are also included. There is also golf and tennis in the area. As an added bonus for animal lovers, this property is also pet-friendly.

"Too good"

Stockbridge, Massachusetts

If you are looking for a vacation rental in Stockbridge, this 4 bedroom, 4 bathroom home is a great option. Staying here will make your trip to Stockbridge fun and convenient. With room for the whole group, this is a great holiday home for the whole family. The 4 bedrooms are neatly arranged so everyone can sleep comfortably. With a king-size bed in the master bedroom and queen-size beds in the other bedrooms, everyone will be comfortable. Within minutes you can reach the Norman Rockwell Museum, the National Shrine of the Divine Mercy, Once Upon a Table and the Main Street Cafe.

A large property in historic Stockbridge

Stockbridge, Massachusetts

This beautiful, historic home is a local landmark. It's big, beautiful and luxurious. This 6 bedroom, 6 bathroom property sleeps up to 12 people. If you are planning a trip with a large family then you should definitely consider this stunning property.

All rooms offer everything guests need. Several bedrooms have king-size beds, so everyone can sleep comfortably. You can eat out or just stay at home and prepare all your meals in the kitchen. There is also plenty of space in the living room, dining room and on the balcony. The site also includes games, a pool table and a BBQ. Add these to your must-see list!

General Williams Estate House

Stockbridge, Massachusetts

Guests love this historic multiple building property and it makes a great place for your Stockbridge vacation. The 6 bedroom, 5 bathroom condo sleeps 16 guests. This place is just the right size for a group outing with big friends. All rooms offer everything guests need. The master has a king bed and the additional bedrooms have queens. Guests enjoy the fully equipped kitchen, which is great for preparing home cooked meals. Everyone can also relax in the living room and dining area.

Not only is this home's pool fun, it's private so you can relax in style. Everyone will also enjoy the game room of this home. On the terrace you can get some fresh air and enjoy some time to relax. The house also includes games, pool table, grill and parking. And the location is also convenient to nearby Berkshire restaurants, shops and activities.

Pittsfield Airbnb and VRBO

Pittsfield is the largest city in the Berkshires but still has a lot of charm and character. There is plenty for the whole family to enjoy. Known as a 'festival town', Pittsfield really comes alive in the summer months when there always seems to be something going on. There's a baseball team in town, lots of parks and lots of activities for the whole family. Children will enjoy a visit to the Berkshire Museum, which has scientific exhibits, an aquarium and even a large playroom. For the young at heart, a trip to Pittsfield isn't complete without a ride on the Berkshires Carousel (only $2).

One of the most popular destinations is the Herman Melville House, also known as Arrowhead. Today it is a museum where you can learn how this famous Moby Dick author lived and worked. Theater lovers can also visit the Colonial Theatre, part of the Berkshire Theater Group.

Because Pittsfield is larger than other cities, many of the properties are slightly smaller. They're also more affordable than what you'll find in other Berkshire towns; So if you are looking for an affordable price this is the place to go.

Lake Front Home in the heart of the Berkshires near Jiminy Peak

Pittsfield, Massachusetts

For anyone looking for a fun vacation in Pittsfield, this 4 bedroom, 4 bath lakehouse is a great vacation rental as it sleeps 10 comfortably. This property would be an amazing option for a large group with all of its extra space and lots of fun lakeside activities. The full kitchen is well equipped and practical, with a microwave, oven and fridge. In the rooms you will find beautiful furniture. One bedroom has a king bed and the other has a queen bed. If you are traveling as a family this is a great option as some of the rooms have bunk beds. And with the dining room, everyone can spread out and relax. Parking, internet, fire pit and grill are also on the list of amenities.

Exquisite apartment in a large Victorian house

Pittsfield, Massachusetts

This historic property is a beautiful and affordable home for a smaller family. The 2 bedroom, 1 bathroom apartment has a great city center location. This amazing apartment has everything you could possibly need and provides it with style too.

The kitchen in this apartment is very good and with oven, fridge and dishwasher you can cook for everyone. With living room, dining room and balcony there is enough space to relax and enjoy. Both bedrooms are beautifully furnished. Both bedrooms have queen size beds which is great for everyone. In this place you also have parking and internet.

4 bedroom lakefront

Richmond, Massachusetts

This renovated and modern lakefront home is a great place to stay during your time in the Berkshires. With 4 bedrooms and 2 bathrooms there is plenty of room for up to 8 guests here, so add it to your wish list. This home is perfect for a large family or group of friends. If you just want to eat out, you can use the fully equipped kitchen to prepare all your meals. And with the beautiful living room, dining room and balcony to spread out on, this home is a great place to relax and unwind. All rooms offer everything guests need. You will find two bedrooms with king-size beds and an additional bedroom with a queen-size bed.

And other amenities can be found here such as games, grill, fire pit and parking. This is a great place to enjoy your next trip to Richmond.

Espaçoso Berkshire Summer Rental, Private Lakeside Dock

Richmond, Massachusetts

A popular vacation rental in the Berkshires, this spacious 3 bedroom, 1 bath home sleeps up to 7 people. It is on the lake and has a jetty. Dive into the water or enjoy the view! This home is perfect for a large family or group of friends. If you are looking for comfort and convenience this is a great home. Within minutes you can reach the Tanglewood Music Center, Bousquet Ski Area, Hancock Shaker Village and the Berkshire Museum.

The kitchen is well equipped with a microwave, dishwasher, stove and oven. There is also the living room, dining room and porch, which offer guests more space. The 3 bedrooms are neatly arranged so that everyone can sleep comfortably. Two of the bedrooms also have queen size beds. Games, BBQ, parking, internet and beach chairs are also on the list of amenities. Pets are also welcome.

Hidden oasis in the Berkshire Mountains

Pittsfield, Massachusetts

This mountain view home in Pittsfield offers many comfortable touches and a relaxing atmosphere on a beautiful lot with stunning landscaping. The 5 bedroom apartment has a long list of features and sleeps up to 10 people. This property would be an amazing option for a large group with all of their extra space. The 5 bedrooms are well laid out so everyone can sleep comfortably. With a king-size bed in the master bedroom and queen-size beds in the other bedrooms, everyone will be comfortable. The microwave, oven and refrigerator in the fully equipped kitchen allow you to cook all of your meals if you wish. Enjoy meals or relax in the living room, dining room and on the balcony of this accommodation.

In this vacation rental you will also find parking, internet, games and a pool table. Places like this book up quickly. Please do not hesitate to bring your pets with you to this accommodation. With the Tanglewood Music Center only 5 miles away and Jiminy Peak Mountain Resort only 5.7 miles away, you will find this to be a very convenient place to stay.

huge designer house

Berkshire County, Massachusetts

The list goes on with this large, modern, and beautiful home in Berkshire County, so be sure to add it to your favorites list. The location of this apartment is perfect. A short distance away you will find the Tanglewood Music Center, Jiminy Peak Mountain Resort, Bousquet Ski Area and the Lee Prime Outlets. This home is perfect for a large family or group of friends. In the rooms you will find beautiful furniture. The master has a king bed and the additional bedroom has a queen.

Berkshire house on the lakefront

Berkshire County, Massachusetts

People love this lakefront home and it's a great place for your Berkshire County vacation. The 2 bedroom, 1 bathroom apartment sleeps 5 people. There is plenty of space for the whole family or group. Each room offers a comfortable place to relax. Staying here will make your trip to the lake fun and convenient. Within minutes you can reach Jiminy Peak Mountain Resort, the Berkshire Museum, Pittsfield State Forest and the Mount Greylock State Reservation Visitor Center.

A beautiful wooden hut in the forest

Pittsfield, Massachusetts

This lake cabin is a popular choice in Pittsfield as it has 2 bedrooms and 1 bath. This cabin is perfect for a large family or group of friends as there is plenty of room for everyone. The 2 bedrooms offer a lot of privacy. Sleep comfortably with a queen-size bed. The kitchen is practical, well equipped and of course has everything you need to prepare your own meals. There is also the living room, dining area and balcony which offer more space for the guests. And you can walk down to the water to enjoy the view or swim in the warmer months.

Grande Barrington Airbnb and VRBO

Great Barrington has one of the largest centers in the Berkshires and there are many restaurants, shops and activities to choose from. Children will also love a visit to the Mahaiwe Theater. For a kid-friendly meal, head to Baba Louie's for pizza, then shop at some of the city's kid-friendly shops. To explore the area's art galleries, head to Housatoni, home to the town's former paper mill.

There are also a number of great child-friendly hiking trails in the area. A family favorite is Monument Mountain, which is not far away and has only a slight incline. There are also several natural bathing and skiing areas in the vicinity of the city.

There are a number of good family holiday homes in the area.

Chic updated home in Great Barrington

Grande Barrington, Massachusetts

A popular vacation rental in Great Barrington, this beautiful and spacious 3 bedroom, 2 bath home sleeps up to 14 people. The view is incredible! Larger groups will love the size of this property. This is a good find for anyone traveling to Great Barrington. On the balcony you can get some fresh air and enjoy the time to relax.

A fully equipped kitchen allows guests to prepare their own meals. All rooms are well furnished. You'll also find more than one bedroom with a queen-size bed. Also on the list of this house are parking, internet and barbecue.

Stunning Victorian renovation

Grande Barrington, Massachusetts

This beautiful and historic property, with all of its extra space, would be an amazing option for a large group. The 5 bedroom, 4 bath home is in a great location. There is also golf and tennis in the area. Check out the photos! If you enjoy vacationing with your dog, know that this is also a pet-friendly property.

Prepare meals in the kitchen as there is a microwave, dishwasher, stove and oven. Each can also spread in the living room, dining room and porch. All rooms offer everything guests need. With a king-size bed in the master bedroom and queen-size beds in the other bedrooms, everyone will be comfortable. Everyone will enjoy the game room of this home. You will also find amenities such as games, barbecue, parking, internet and garage.

Berkshires Lakeside Retreat

Grande Barrington, Massachusetts

This lakefront home with dock is a popular choice in Great Barrington as it has 4 bedrooms and 2 bathrooms. If you're planning a family getaway, be sure to consider this large home. In the rooms you will find beautiful furniture. The queen-size bed ensures a good night's sleep. With the microwave and oven in the fully equipped kitchen you can prepare all your meals if you wish.

Parking, internet and BBQ facilities are also included. You will also find Pleasant and Main and the Brick House Pub less than 3 miles away. If you are looking for comfort and convenience this is a great home.

Deluxe house with pool

Grande Barrington, Massachusetts

This home is a great place to stay in Great Barrington.

The pool is a fantastic addition to the home that everyone will enjoy. With 4 bedrooms and 2 bathrooms there is plenty of room for up to 8 guests here, so add it to your wish list. There is plenty of space for the whole family or group. And with a living room, dining room and balcony, everyone can spread out and relax. In the rooms you will find beautiful furniture. There are king beds in two bedrooms and queen beds in the other bedrooms.

You will also find amenities such as games, barbecue, parking, internet and table tennis table. It's hard to find a place like this so check before you book.

rural castle

Grande Barrington, Massachusetts

This unique castle-style Great Barrington home offers a host of comfortable touches and a relaxing atmosphere. The 3 bedroom, 3 bathroom apartment has a long list of features and sleeps up to 8 people. This is a family friendly place with enough space for everyone. Or it could be good for a group of friends. Each room offers a comfortable place to relax. You will find two bedrooms with king-size beds and an additional bedroom with a queen-size bed. There is a fully equipped kitchen for those who enjoy cooking. And with the beautiful living room to spread out in, this home allows you to relax and unwind.

In this apartment you will also find parking, internet, garage and barbecue. Places like this book up quickly. As an added bonus, your pets are also welcome.

open country house

Grande Barrington, Massachusetts

Staying here will make your trip to Great Barrington fun and convenient. This 3 bedroom, 2 bathroom home sleeps up to 5 people. This is a family friendly place with enough space for everyone. Or it could be good for a group of friends.

Each room offers a comfortable place to relax. The queen beds in two of the bedrooms have good mattresses. If you just want to eat out, you can use the fully equipped kitchen to prepare all your meals. With a living room and a dining room, there is enough space to relax and enjoy. And more amenities can be found here, such as parking, internet and barbecue.

Large Barrington apartment

Grande Barrington, Massachusetts

This is a spacious and beautiful 2 bedroom, 1 bathroom apartment. It can accommodate up to 5 people. There is plenty of space for the whole family or group. Both bedrooms offer everything guests could need. Queen size beds have good mattresses. You'll feel right at home in the living and dining room, which offers even more space to relax. Guests appreciate the convenience of the fully equipped kitchen at this property. This amazing apartment has everything you could possibly need and provides it with style too.

GB center apartment

Grande Barrington, Massachusetts

Visitors love this apartment and it is a great place for your vacation in Great Barrington. The 2 bedroom, 1 bathroom apartment sleeps 5 people. This is a great option for a family as there is room for everyone. Both bedrooms are beautifully furnished. Since both bedrooms are furnished with queen-size beds, everyone can sleep comfortably. Prepare your meals in the kitchen, which features modern appliances such as a microwave, dishwasher, stove and oven. With a living room and a dining room, there is enough space to relax and enjoy.

Williamstown Airbnb and VRBO

Williamstown, Massachusetts is a charming college town in the northern part of the Berkshires. It's a great place for families who enjoy hiking and visiting museums. The town is home to Williams College with some great galleries and museums. Visitors especially appreciate theWilliams College Art Museumit is atClark-Museum, which is outside of the city center.

There are also a number of great walking areas close to the city. Outside of town is Mount Greylock, the highest peak in Massachusetts. Also nearby are Taconic Trail State Park, Field Farm and Bullock Forest.

Williamstown has a wide variety of rental properties to choose from. There are smaller, more affordable condos and apartments, but families tend to take advantage of the larger homes, which offer more bedrooms, larger kitchens, and outdoor space where the whole family can play.

Chic Berkshire dolls house

Willianstown, Massachusetts

A popular vacation rental in Williamstown, this spacious 3 bedroom, 2 bath home sleeps up to 6 people. This is a great option for a family as there is room for everyone. This is a great place to enjoy your next trip to Williamstown. It is in a great location near Williams College and the Sterling and Francine Clark Art Institute.

You can eat out or just stay at home and prepare all your meals in the kitchen. And with the living and dining room, everyone can spread out and relax. In the rooms you will find beautiful furniture. Several rooms have queen-size beds, which is great for everyone to relax. They are very well furnished. A BBQ, parking, internet and garage are also included.

Huge, luxurious, Victorian, updated Williamstown

Willianstown, Massachusetts

This is a spacious and beautiful 5 bedroom, 5 bath historic home. It can accommodate up to 10 people. This large home is perfect for a large family or group of friends. All rooms offer everything guests need. One bedroom has a king bed and several other rooms have queen beds. There's even more lounging space in the living room, dining room, and lanai. The kitchen is practical, well equipped and of course has everything you need to prepare your own meals. As an added bonus, your pets are also welcome.

Walk downtown and to the museums in Williamstown

Willianstown, Massachusetts

People love this home and it is a great place for your Williamstown vacation. The 5 bedroom, 3 bathroom apartment sleeps 16 people. This place is just the right size for a group outing with big friends. All rooms offer everything guests need. One bedroom has a king bed while the others have queen beds. Prepare your meals in the kitchen, which features modern appliances such as a microwave, dishwasher and stove. There is also the living room and dining area, which offers guests more space.

In this place you also have games, grill, parking and internet. It's hard to find a place like this so check before you book. This is also a pet friendly place. Williams College, the Williamstown Theater Festival and the Sterling and Francine Clark Art Institute are within five miles of this location.

11 acre mid-century estate

Willianstown, Massachusetts

This home on a large natural lot is a popular choice in Williamstown as it has 4 bedrooms and 3 bathrooms. With room for the whole group, this is a great holiday home for the whole family. All rooms are well furnished. Since two of the bedrooms have king-size beds, everyone can sleep comfortably. You can prepare your own meals in the fully equipped kitchen with a microwave, dishwasher and stove. There's even more lounging space in the living room, dining room, and lanai.

Do you need a private pool? Doesn't everyone do that? This place has one, and it's awesome. Also on the list of this home is a grill, parking, internet and fire pit. This place is minutes away from Williams College, Pera Mediterranean Bistro, and Spice Root Modern Indian Cuisine. This is a convenient option for anyone traveling to Williamstown.

quiet farmhouse

Willianstown, Massachusetts

This mountain view home is a great place to base yourself during your stay in Williamstown. Williams College and the Sterling and Francine Clark Art Institute are less than a mile away.

With 3 bedrooms and 1 bathroom there is plenty of room for up to 8 guests here, so add it to your wish list. There is plenty of space for the whole family or group. Guests enjoy the fully equipped kitchen, which is great for preparing home cooked meals. There is also the living room and dining area, which offers guests more space. The 3 bedrooms are neatly arranged so that everyone can sleep comfortably. The master has a king bed and the additional bedroom has a queen.

In this apartment you will also find internet and a barbecue. This is a good find for anyone heading to Williamstown. And you can bring the furry family members as this place is pet friendly.

Cozy renovated cabin in Williamstown

Willianstown, Massachusetts

If you are looking for a vacation rental with mountain views in Williamstown, this 2 bedroom, 2 bath cabin is a great option. This is a convenient option for anyone traveling to Williamstown. This is a great option for a family as there is room for everyone. Each room offers a comfortable place to relax. Sleep comfortably with a queen-size bed. The microwave, dishwasher and stove in the fully equipped kitchen allow you to prepare all your meals if you wish. And with the beautiful living room, dining room and balcony to spread out on, this cabin is a great place to relax and unwind.

This cabin also has modern conveniences like games, grill, parking and internet. You will also find Williams College, Mount Greylock, the Williamstown Theater Festival and the Sterling and Francine Clark Art Institute all less than 5 miles away.

See Airbnb and VRBO

Lee has a historic downtown and relaxed vibe that visitors love. Downtown is home to several historic buildings, including the Congregational Church, the Lee Library, and the Civil War Memorial. There are also a number of Victorian houses in the area.

Outside the city center, visitors can shop at the nearby mall. There are also a number of restaurants in the area. Kids and adults alike will enjoy spending time at Laurel Lake, which offers the quintessential mountain experience.

The concierge at the Golden Hill

Berkshire County, Massachusetts

This home is a popular choice for a Lee stay as it has 4 bedrooms and 4 bathrooms. This home is a great choice for multiple families traveling together. All rooms offer everything guests need. And with multiple bedrooms featuring queen beds, everyone can sleep comfortably. With the microwave and oven in the fully equipped kitchen you can prepare all your meals if you wish. Parking, internet and BBQ facilities are also included.

Impressionante Post & Beam Home

Berkshire County, Massachusetts

Guests love this unique, well designed home and it is a great place for your Berkshires vacation. The 5 bedroom, 3 bathroom apartment sleeps 14 people. With room for so many people, this large home is a great choice for families traveling together. Each room offers a comfortable place to relax. One bedroom has a king bed while the others have queen beds. One bedroom has bunk beds that the kids will love. The kitchen is well equipped with a microwave, dishwasher, stove and oven. Each can also spread in the living room, dining room and porch.

This home also has modern conveniences such as games, BBQ and parking. Staying here will make your trip to Berkshire County fun and convenient. The location is very convenient as the Divine Mercy National Sanctuary, Lee Prime Outlets, Salmon Run Fish House and Timothy's Restaurant are all less than 3 miles away.

Berkshire's sprawling estate

Lee, Massachusetts

This is a large and beautiful 4 bedroom, 1 bath home with mountain views. It can accommodate up to 6 people. There is plenty of space for the whole family or group. In the rooms you will find beautiful furniture. One bedroom has a king bed and the other has a queen bed. There is even more space to relax in the living room and on the veranda. A fully equipped kitchen allows guests to prepare their own meals.

You'll love hanging out on the porch and soaking up the atmosphere. This place will quickly feel like a second home.

Beautiful, private, family atmosphere, organic house

Lee, Massachusetts

For anyone looking for a fun vacation in Lee, this 3 bedroom, 2 bath home is a great vacation home as it sleeps 6 people. This home is perfect for a large family or group of friends. You can prepare your own meals in the fully equipped kitchen with microwave and dishwasher. The 3 bedrooms are neatly arranged so that everyone can sleep comfortably. This house also has a living room and dining area where you can comfortably relax during your trip. And other amenities can be found here, such as games, barbecue and parking. This is also a pet friendly place. Go out onto the balcony and enjoy the view. With golf and tennis nearby this is the perfect place to use as a base. This is a convenient option for anyone traveling to Lee.

Nord-Adams

North Adams is home to several historic churches giving it an enchanting skyline. The area is full of forests, parks and beautiful landscapes. Visitors enjoy visiting the Massachusetts Museum of Contemporary Art, the largest contemporary art museum in the country. For kids who love trains, a visit to Western Gateway Heritage State Park is fun. It is located in the restored freight station district and features a number of railway exhibitions. Also nearby is Natural Bridge State Park and a number of excellent hiking trails.

spacious victorian

North Adams, Massachusetts

This is a 4 bedroom historic Victorian home that is large, beautiful and stunning. It can accommodate up to 9 people. This is a large room and would be perfect for a large family or multiple families holidaying together. The location is perfect as it is close to many activities, shops and restaurants in town. Or you can easily drive to other nearby cities or even Vermont.

If you are interested in other accommodation options in the Berkshires, see alsoRomantic Berkshires getaways for a couples getaway.

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