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Great Barrington, MA short term rentals
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Best Short term and Weekly rentals in Great Barrington, MA

Explore Family Short-Term Rentals in Great Barrington, MA

These short-term rentals in Great Barrington, MA are ideal for families, offering fresh air and trail access right outside with room for everyone.

Luxury Fox Hollow Estate Home On Laurel Lake - Dream Location, Hot Tub, Kayaks++ - Great Barrington, MA
9.4 65 reviews
Great Barrington, MA
07/26 – 08/04
$721/nighttotal: $6489 (9 )

Luxury Fox Hollow Estate Home On Laurel Lake - Dream Location, Hot Tub, Kayaks++

5 7
apartment , Lee
This waterfront Cape Cod-style house is situated in the heart of Lenox, within walking distance of the Edith Wharton Estate and a short drive from Lee's cultural attractions and outdoor activities. The house has an excellent user rating.
The house has a floor area of 2700 square feet and can accommodate up to 14 guests. It has 5 bedrooms, 3 bathrooms, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, a jacuzzi, a garden, and parking. The house also offers amenities such as a pool table, HD Smart TVs, wood-burning fireplaces, a wine cooler, a hot tub, an outdoor barbecue, a tennis court, kayaks, canoes, and a rowboat.
Prime Location, Recently Redesigned, Riverfront! - Great Barrington, MA
10 5 reviews
Great Barrington, MA
07/26 – 08/04
$624/nighttotal: $5616 (9 )

Prime Location, Recently Redesigned, Riverfront!

4 7
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.
Historic Rectory Retreat In Stockbridge  Getaway For 8-12 Guests - Great Barrington, MA
10 11 reviews
Great Barrington, MA
07/24 – 07/26
$1263/nighttotal: $2526 (2 )

Historic Rectory Retreat In Stockbridge Getaway For 8-12 Guests

5 10
apartment , Stockbridge
This Stockbridge vacation home offers a central location, within a 10-minute walk of Schantz Galleries, the Housatonic River, and Mission House, and less than a mile from the Berkshire Theatre Festival and Naumkeag Museum.
This five-bedroom, two-bathroom house sleeps twelve guests and includes amenities such as free WiFi, a fully equipped kitchen with a refrigerator and dishwasher, a fireplace, and a washing machine; housekeeping is available upon request.
Berkshire Retreat At Cantina 229 - Great Barrington, MA
10 10 reviews
Great Barrington, MA
07/24 – 07/26
$1045/nighttotal: $2090 (2 )

Berkshire Retreat At Cantina 229

1 10
apartment , New Marlborough
This five-bedroom, three-bathroom home in New Marlborough, Massachusetts, is a beautifully restored 1911 house situated on five private acres, 15 minutes from Great Barrington and adjacent to the farm-to-table restaurant Cantina 229.
The 2,584-square-foot residence boasts a spacious layout, accommodating up to 10 guests and featuring a fully equipped kitchen, a basement with games and laundry facilities, and access to outdoor amenities including a fire pit and expansive lawns; nearby activities include hiking and skiing in the Berkshires.

Best Great Barrington, MA lodging with a balcony

Walk To Town/lake, 25 Renovation! - Great Barrington, MA
9.8 94 reviews
Great Barrington, MA
07/24 – 07/26
$1293/nighttotal: $2586 (2 )

Walk To Town/lake, 25 Renovation!

3 10
apartment , Great Barrington
This house in Great Barrington is conveniently located within walking distance of the Mahaiwe Performing Arts Center, the Housatonic River Walk, and the Housatonic River, placing you right in the heart of the town's cultural and recreational scene. The home has received excellent ratings for location, cleanliness, and overall user experience.
This 1500 square foot house has 3 bedrooms, 2 bathrooms, and can comfortably accommodate up to 11 guests. The property includes a fully equipped kitchen, a garden, a fireplace, and a barbecue grill, making it perfect for relaxing and enjoying the outdoors.
Fantastic 2-bedroom House With Ac In Quaint Hillsdale. - Great Barrington, MA
Great Barrington, MA
07/26 – 08/04
$742/nighttotal: $6678 (9 )

Fantastic 2-bedroom House With Ac In Quaint Hillsdale.

3 7
apartment , Copake Falls
This pet-friendly vacation home in Copake Falls offers immediate access to winter sports, situated just a 1-minute walk from Catamount Ski Area and 11 minutes from Catamount Aerial Adventure Park.
This 3-bedroom, 2-bathroom apartment accommodates up to 7 guests and features a full kitchen, air conditioning, Wi-Fi, a swimming pool, and a garden, with on-site parking available.
Chambery Inn - Great Barrington, MA
9.6 405 reviews
Great Barrington, MA
07/24 – 07/26
$4303/nighttotal: $8606 (2 )

Chambery Inn

5 10
B&B , Lee
Situated in the heart of Lee, this centrally located B&B is just 1.7 miles from Lee Premium Outlets and offers easy access to the town's attractions and amenities. With excellent user, location, and cleanliness ratings, this B&B ensures a comfortable and enjoyable stay.
The B&B features a charming garden, a spa tub, and spa services for relaxation and rejuvenation. Guests can enjoy free WiFi, parking, and a snack bar/deli for convenience. The B&B also offers express check-out and complimentary newspapers for added ease and comfort.

Frequently Asked Questions about short term rentals in Great Barrington, MA

  • Which top landmarks shouldn't you miss in and around Great Barrington, MA?

    You definitely want to check out the historic Mahaiwe Performing Arts Center in downtown Great Barrington. It's a beautiful theater that hosts concerts, plays, and other events. If you're into history, the Old First Church is a must-see. It was built in the 18th century and is a beautiful example of colonial architecture. And if you're looking for something a little more modern, the Great Barrington Rail Trail is a great place to go for a walk or bike ride.
  • What are the best short term rentals in Great Barrington, MA?

    Among the short term rentals in Great Barrington, MA, A Cozy Retreat In Nature - An Art Lover’s Dream, Cottage On Scenic Road and Ski Berkshire Get Away In Gb are the most popular ones.

  • What notable natural landmarks are near Great Barrington, MA?

    Just a short drive away, you'll find Mount Everett, the highest point in the Berkshires. It's a great place to hike and enjoy the views. And for a more relaxing experience, head to Lake Buel or Lake Mansfield. They're both beautiful spots to go swimming, kayaking, or just relax by the water.
  • What are the best short term rentals with a pool in Great Barrington, MA?

  • What family-friendly activities are available near Great Barrington, MA?

    The Great Barrington Farmers Market is a great place to bring the kids on Saturdays. There's always live music and plenty of things to see and do. The Berkshire Botanical Garden is another great option. It's a beautiful place to walk around and learn about different plants and flowers. And if you're looking for something a little more active, the Great Barrington Rail Trail is a great place to go for a bike ride or walk.
  • What are the best short term rentals with a jacuzzi in Great Barrington, MA?

  • What kind of weather can travelers expect in Great Barrington, MA?

    Great Barrington has four distinct seasons. Summers are warm and humid, with average highs in the 80s. Winters are cold and snowy, with average lows in the 20s. Spring and fall are mild and pleasant, with average temperatures in the 50s and 60s. Be sure to pack for all types of weather!
  • What are the best short term rentals for families and kids in Great Barrington, MA?

  • What major cities can be found near Great Barrington, MA?

    Great Barrington is located in the Berkshires, about a two-hour drive from both Boston and New York City. It's also about an hour from Albany, NY, and Hartford, CT.

Destinations nearby

Best Great Barrington, MA lodging with a kitchen

Nature Retreat Near Prospect Lake - Great Barrington, MA
Great Barrington, MA
07/24 – 07/26
$729/nighttotal: $1458 (2 )

Nature Retreat Near Prospect Lake

3 10
apartment , Egremont
This 3-bedroom, 1-bathroom Berkshires rental is located in Egremont, directly across from French Park offering immediate access to trails, tennis, and a playground, and is a short drive from local dining.
This pet-friendly apartment accommodates up to 11 guests and features a granite kitchen, wood-burning fireplace, 3-season porch, outdoor fire pit, Blackstone grill, and pizza oven.
Four Villas L Arcade, Pool & Forest Views Awaits - Great Barrington, MA
Great Barrington, MA
07/02 – 07/06
$937/nighttotal: $3748 (4 )

Four Villas L Arcade, Pool & Forest Views Awaits

8 4
B&B , Lee
This Bed and Breakfast in Lee, nestled in the Berkshires, offers proximity to hiking, boating, and skiing, with the Appalachian Trail just a short distance away, and is also conveniently located a short drive from the Norman Rockwell Museum and Tanglewood. This 8-bedroom, 8-bathroom inn accommodates up to 24 guests, providing spacious rooms with kitchens, an indoor heated pool, a public fitness center, and complimentary toiletries and basic kitchen amenities, with free parking available.
Historic (Updated)1812 Federal Brick House Well Situated In Berkshires With Pool - Great Barrington, MA
9.0 2 reviews
Great Barrington, MA
07/26 – 08/04
$1461/nighttotal: $13149 (9 )

Historic (Updated)1812 Federal Brick House Well Situated In Berkshires With Pool

4 7
apartment , Sheffield
This historic brick house is located in the Berkshires of Western Massachusetts, just minutes from Great Barrington and close to the Connecticut and New York borders, offering a peaceful retreat in a picturesque setting. The property has received excellent ratings for user experience, location, and cleanliness.
This spacious home features 4 bedrooms and can accommodate up to 8 guests, providing ample space for families or groups of friends. The home offers a variety of amenities, including a swimming pool, tennis court, fitness center, and a studio building with an art library and living room, making it perfect for relaxation, recreation, and entertainment.
Family Basecamp | 3 Villas, Pools & Games - Great Barrington, MA
Great Barrington, MA
07/02 – 07/06
$703/nighttotal: $2812 (4 )

Family Basecamp | 3 Villas, Pools & Games

6 4
B&B , Lee
This B&B in Lee, located in the Berkshires, is situated near hiking, boating, and skiing opportunities, as well as the Norman Rockwell Museum, Tanglewood, and the Appalachian Trail.
This 6-bedroom, 6-bathroom bed and breakfast accommodates up to 18 guests and features spacious rooms, a kitchen with a fridge and microwave, air conditioning, a swimming pool, garden, and fitness center, with complimentary parking for one vehicle.

Best Great Barrington, MA lodging with laundry available

Pothul Perch | Walk To Lake • Sleeps 8 - Great Barrington, MA
9.8 13 reviews
Great Barrington, MA
07/26 – 08/04
$613/nighttotal: $5517 (9 )

Pothul Perch | Walk To Lake • Sleeps 8

1 7
apartment , Great Barrington
This four-bedroom house in Great Barrington sits on a hill, a short walk from downtown shops and restaurants and a few blocks from Lake Mansfield.
The 8-guest rental boasts two full bathrooms, a fully equipped kitchen with dishwasher and freezer, a garage with storage for outdoor gear, plus a patio with a gas grill and outdoor fireplace, perfect for entertaining.
North Egremont Historic House - Great Barrington, MA
Great Barrington, MA
07/26 – 08/04
$390/nighttotal: $3510 (9 )

North Egremont Historic House

1 7
apartment , Egremont
This 1840s farmhouse in Egremont, Massachusetts, sits near the base of Baldwin Hill, a short walk from French Park and Prospect Lake, and 30 minutes from Tanglewood.
This three-bedroom, two-bathroom home sleeps seven, boasting a fully equipped kitchen with a dual-fuel stove and air fryer microwave, a two-acre lot with a deck, and proximity to hiking trails, tennis courts, and swimming at Prospect Lake.
Hudson Valley Meets Berkshires. Modern Vacation Home W/ Upscale Comforts - Great Barrington, MA
Great Barrington, MA
07/02 – 07/06
$879/nighttotal: $3516 (4 )

Hudson Valley Meets Berkshires. Modern Vacation Home W/ Upscale Comforts

3 4
apartment , Copake Lake
This Hillsdale rental is located near the Berkshires and Hudson Valley, offering 3 bedrooms and 2 bathrooms for up to 6 guests.
Enjoy a wood-burning fireplace, projector, outdoor fire pit, and fast WiFi in this modern mid-century designed home, perfect for exploring nearby hiking trails and nature.
Berkshire Summer Chalet W/ Pool + Private Hiking - Great Barrington, MA
9.2 10 reviews
Great Barrington, MA
07/26 – 08/04
$1179/nighttotal: $10611 (9 )

Berkshire Summer Chalet W/ Pool + Private Hiking

1 7
apartment , Great Barrington
This four-bedroom cabin is located in the foothills of the Appalachian Trail, a short drive from the center of Great Barrington, Massachusetts.
The cabin offers a spacious and modern design with 30-foot ceilings, a refinished swimming pool, and multiple patios, decks, and balconies for outdoor enjoyment.
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