Vacation rentals in Great Barrington, MA

173 available vacation rental offers

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Great Barrington, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Great Barrington, MA

Our Favorite Family-Friendly Vacation Rentals in Great Barrington, MA

Make memories with a family retreat in Great Barrington, MA, where fresh air and scenic trails are right outside your door.

Stunning Renovated Victorian - Great Barrington, MA
10 56 reviews
Great Barrington, MA
07/26 – 08/04
$1785/nighttotal: $16065 (9 )

Stunning Renovated Victorian

5 2
apartment , Great Barrington
This spacious home is located in the "Hill" neighborhood of Great Barrington, a short walk from Lake Mansfield and a quick drive to downtown shops and restaurants. The apartment has received excellent ratings for its amenities and location.
This 5000 square foot home comfortably accommodates up to 12 guests with five bedrooms and five bathrooms. It features a gourmet kitchen, a screened porch, a private patio with a hot tub, a tennis court, and a playset for children.
Stunning Renovated Victorian, Walk To Town - Great Barrington, MA
10 8 reviews
Great Barrington, MA
07/26 – 08/04
$1598/nighttotal: $14382 (9 )

Stunning Renovated Victorian, Walk To Town

1 2
apartment , Great Barrington
This spacious 5-bedroom home is located in a quiet cul-de-sac just a short walk from downtown Great Barrington, making it easy to explore the town's shops, restaurants, and attractions. The property has received excellent ratings for its location, cleanliness, and overall guest experience.
The house is perfect for large families or groups, with room for up to 12 guests. Guests can enjoy a variety of amenities, including a chef's kitchen, a hot tub, a screened porch with a ping pong table, and a private stone patio with a BBQ.
Prime Location, Recently Redesigned, Riverfront! - Great Barrington, MA
10 5 reviews
Great Barrington, MA
07/26 – 08/04
$626/nighttotal: $5634 (9 )

Prime Location, Recently Redesigned, Riverfront!

4 2
apartment , Great Barrington
This four-bedroom Great Barrington apartment, a historic factory conversion, is conveniently located near Butternut, Catamount, and Bousquet ski resorts, offering easy access to Berkshire outdoor activities.
The 4-bedroom rental boasts a spacious layout with two bathrooms, a grand piano, two wood-burning fireplaces, a fenced yard for two dogs (additional $50 per dog), and parking for six vehicles, comfortably accommodating eight guests.

Best Great Barrington, MA vacation rentals with a balcony

King Bed|wi-fi|2m Ski Resort|studio - Great Barrington, MA
9.6 98 reviews
Great Barrington, MA
07/26 – 08/04
$155/nighttotal: $1395 (9 )

King Bed|wi-fi|2m Ski Resort|studio

1 2
apartment , Great Barrington
This remodeled mid-century modern studio apartment is located in Great Barrington, Massachusetts, 1.5 miles from downtown and 1.3 miles from the Mahaiwe Performing Arts Center.
The pet-friendly unit sleeps two, features a king-size bed, high-speed internet, a 58" TV with Hulu + Live TV, a SMEG coffee maker, and a mini-fridge; shared guest amenities include a microwave.

Frequently Asked Questions about vacation rentals in Great Barrington, MA

  • What are some interesting places to visit in or near Great Barrington, MA?

    There are tons of cool spots in and around Great Barrington! You've got the Mahaiwe Performing Arts Center for a show, the Great Barrington Historical Society museum if you're into history, and the Mount Everett State Reservation for some hiking and stunning views. If you're up for a short drive, the Clark Art Institute in Williamstown is a must-see.
  • What are the best Airbnb and vacation rentals in Great Barrington, MA?

    A Cozy Retreat In Nature - An Art Lover’s Dream, Ski Berkshire Get Away In Gb and Secluded But Not Isolated Berkshire Retreat are the most popular Airbnb and vacation rentals in Great Barrington, MA among travelers.

  • Which walking or cycling routes are the best in Great Barrington, MA?

    Great Barrington is a walker's paradise! The Hop Brook Trail is a lovely, flat walk along the river, and the Barrington Rail Trail is great for biking, especially for families. If you're feeling ambitious, the Mount Everett State Reservation has some challenging hikes with breathtaking views.
  • What are the most popular Airbnbs in Great Barrington, MA?

  • What sports or outdoor activites can visitors enjoy in and around Great Barrington, MA?

    Great Barrington is a haven for outdoor enthusiasts! You can go hiking, biking, and kayaking on the Housatonic River. There's also great skiing and snowboarding at Catamount Mountain Resort in nearby Egremont, and the Great Barrington Golf Club is a fantastic option for golfers.
  • What are the best vacation rentals with a pool in Great Barrington, MA?

  • What other towns or cities can be easily accessed from Great Barrington, MA?

    Great Barrington is a great base for exploring the Berkshires! You can easily drive to Stockbridge, home to the Norman Rockwell Museum, or Lenox, famous for its Tanglewood Music Festival. If you want a bigger city, Albany, NY is about an hour and a half drive.
  • What are the best rentals for families and kids in Great Barrington, MA?

  • What amenities are commonly available in vacation rentals in Great Barrington, MA?

    Vacation rentals in Great Barrington usually come with the basics, like a kitchen, bathroom, and bedrooms. Many also have amenities like a fireplace, outdoor space, and even a hot tub. You'll find a wide range of options, so you can pick the perfect place based on your needs and budget.
  • What are the best rentals or Airbnbs with a jacuzzi in Great Barrington, MA?

  • What time of year is best to rent a vacation rental Great Barrington, MA?

    Great Barrington is beautiful year-round! Fall is a popular time to visit, with the stunning foliage. Summer is great for outdoor activities, and winter offers snow sports and cozy evenings by the fire. The best time to visit really depends on your interests.
  • What are the local dishes in Great Barrington, MA region?

    The Berkshires are known for their farm-to-table cuisine! You'll find lots of delicious local options, like the Berkshire pork and apple cider donuts. And don't forget to try the maple syrup and cheese from the area's farms. You'll find plenty of great restaurants in Great Barrington serving these local specialties.

Destinations nearby

Best Great Barrington, MA vacation rentals with a sauna

Berkshire Retreat|king Bed|wi-fi|2m Ski Resort - Great Barrington, MA
9.8 156 reviews
Great Barrington, MA
07/26 – 08/04
$155/nighttotal: $1395 (9 )

Berkshire Retreat|king Bed|wi-fi|2m Ski Resort

1 2
apartment , Great Barrington
This remodeled mid-century motel is located in Great Barrington, just a short drive from the downtown area and the Mahaiwe Performing Arts Center. The apartment has received excellent ratings for location, cleanliness, and overall experience.
This charming apartment features one bedroom and one bathroom, comfortably accommodating two guests. Amenities include a king-sized bed, a 55-inch TV with the NFL package, high-speed internet, air conditioning, a swimming pool, a garden, and parking.

Best Great Barrington, MA vacation rentals with a fireplace

Renovated 4br With Pool & Views 5mins To Gb Town - Great Barrington, MA
Great Barrington, MA
07/26 – 08/04
$1466/nighttotal: $13194 (9 )

Renovated 4br With Pool & Views 5mins To Gb Town

4 2
apartment , Great Barrington
This four-bedroom Great Barrington house offers a central location, providing easy access to the town's shops, restaurants, and cultural attractions.
The 4-bedroom, 3-bathroom home features a private pool, fully equipped kitchen, and accommodates up to six guests, perfect for families or groups seeking a peaceful yet convenient Berkshires getaway.
Stunning Renovated Victorian, Walk To Town - Great Barrington, MA
10 8 reviews
Great Barrington, MA
07/26 – 08/04
$1598/nighttotal: $14382 (9 )

Stunning Renovated Victorian, Walk To Town

1 2
apartment , Great Barrington
This spacious 5-bedroom home is located in a quiet cul-de-sac just a short walk from downtown Great Barrington, making it easy to explore the town's shops, restaurants, and attractions. The property has received excellent ratings for its location, cleanliness, and overall guest experience.
The house is perfect for large families or groups, with room for up to 12 guests. Guests can enjoy a variety of amenities, including a chef's kitchen, a hot tub, a screened porch with a ping pong table, and a private stone patio with a BBQ.
Stunning Renovated Victorian - Great Barrington, MA
10 56 reviews
Great Barrington, MA
07/26 – 08/04
$1785/nighttotal: $16065 (9 )

Stunning Renovated Victorian

5 2
apartment , Great Barrington
This spacious home is located in the "Hill" neighborhood of Great Barrington, a short walk from Lake Mansfield and a quick drive to downtown shops and restaurants. The apartment has received excellent ratings for its amenities and location.
This 5000 square foot home comfortably accommodates up to 12 guests with five bedrooms and five bathrooms. It features a gourmet kitchen, a screened porch, a private patio with a hot tub, a tennis court, and a playset for children.
Prime Location, Recently Redesigned, Riverfront! - Great Barrington, MA
10 5 reviews
Great Barrington, MA
07/26 – 08/04
$626/nighttotal: $5634 (9 )

Prime Location, Recently Redesigned, Riverfront!

4 2
apartment , Great Barrington
This four-bedroom Great Barrington apartment, a historic factory conversion, is conveniently located near Butternut, Catamount, and Bousquet ski resorts, offering easy access to Berkshire outdoor activities.
The 4-bedroom rental boasts a spacious layout with two bathrooms, a grand piano, two wood-burning fireplaces, a fenced yard for two dogs (additional $50 per dog), and parking for six vehicles, comfortably accommodating eight guests.
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