Compare temporary rentals in Great Barrington, MA from 100+ providers!
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Best Short term and Weekly rentals in Great Barrington, MA
Great Barrington, MA
07/26 – 08/04
$749/nighttotal: $6741 (9 )
Pothul Perch | Walk To Lake Sleeps 8
4 7
apartment , Great Barrington
This four-bedroom, two-bathroom house in Great Barrington is located a 14-minute walk from Lake Mansfield Park and a 3-minute drive from the Mahaiwe Performing Arts Center. This 3,500 square foot residence accommodates up to eight guests with amenities including a full kitchen with a microwave and dishwasher, free Wi-Fi, a private barbecue, and a garden.
10 56 reviews
Great Barrington, MA
07/26 – 08/04
$1627/nighttotal: $14643 (9 )
Stunning Renovated Victorian
5 7
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.
Great Barrington, MA
07/26 – 08/04
$638/nighttotal: $5742 (9 )
Tranquil 4-bedroom Aspen Like Cabin
1 7
cabin , Ghent
This private mountain lodge is situated on over 283 acres, offering a secluded setting less than 10 miles from Catamount and Butternut Mountain ski resorts. This 7-guest capacity lodge features an open floor plan with a stone fireplace, two full kitchens, 2.5 bathrooms, smart TVs, and access to hiking trails, a pond for swimming, and fishing.
9.6 4 reviews
Great Barrington, MA
07/02 – 07/06
$370/nighttotal: $1480 (4 )
It's All About The Mountain Views, Modern Farmhouse
1 4
apartment , Ghent
This family-friendly vacation home is located just 20 kilometers from Catamount Aerial Adventure Park, Catamount Ski Area, and Omi International Arts Center, offering a peaceful mountain retreat near popular attractions. The house has received excellent user ratings, making it a popular choice for travelers seeking a comfortable and enjoyable stay. This one-bedroom, one-bathroom house can accommodate up to six guests, making it ideal for families or groups of friends. The house offers a range of amenities, including a fully equipped kitchen, a spa tub, a fireplace, a terrace, a garden, and parking, ensuring a relaxing and enjoyable stay.
9.7 39 reviews
Great Barrington, MA
07/26 – 08/04
$971/nighttotal: $8739 (9 )
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
1 7
apartment , Stockbridge
This Stockbridge apartment offers a unique and exclusive rental option for travelers seeking a luxurious and spacious accommodation in the heart of the Berkshires. The apartment boasts an excellent user, location, and cleanliness rating, ensuring a comfortable and memorable stay. With its sprawling 2,000 square feet of living space, four bedrooms, and four bathrooms, the apartment comfortably accommodates up to eight guests. The fully equipped kitchen, expansive outdoor space, and access to a private swimming pool and lush grounds provide an unparalleled level of comfort and relaxation. The apartment's proximity to popular tourist destinations in Stockbridge makes it an ideal base for exploring the region's cultural and natural attractions.
Great Barrington, MA
07/02 – 07/06
$937/nighttotal: $3748 (4 )
Villa Retreat | Four Rooms, Sauna, Courts & Bbq
8 4
B&B , Lee
This B&B in Lee, nestled in the Berkshires, is located a short drive from the Norman Rockwell Museum and Tanglewood, offering convenient access to hiking, boating, skiing, and the Appalachian Trail. This accommodation features 8 spacious bedrooms, 8 bathrooms, and a guest capacity of 24, with amenities including a kitchen, air conditioning, an indoor swimming pool, a fitness center, and complimentary parking.
Great Barrington, MA
07/26 – 08/04
$465/nighttotal: $4185 (9 )
The Docent's House - Honoring A Legacy
1 7
apartment , Great Barrington
This Great Barrington home offers proximity to key Black History landmarks, including the W.E.B. Du Bois Boyhood Homesite (15 miles) and Clinton AME Zion Church (10 miles), with downtown Great Barrington's River Walk just 8 miles away. This 4-bedroom, 2-bathroom residence sleeps 8 guests and features a fully-equipped kitchen, air conditioning, indoor gas fireplace, outdoor dining, and is 3 miles from Ski Butternut, with the Norman Rockwell Museum 17 miles and Tanglewood 22 miles distant.
10 10 reviews
Great Barrington, MA
07/24 – 07/26
$1135/nighttotal: $2270 (2 )
Guesthouse Cabin Vacation Rentals In Berkshire County
4 10
cabin , Mount Washington
Undermountain Lodge is a short drive from Mount Washington's cultural attractions like Ashley House and Mahaiwe Performing Arts Center, and sits between two natural spring lakes in Sheffield, offering a serene escape. The lodge has earned excellent user ratings. The four-bedroom cabin comfortably sleeps 12 guests and features a spacious living room, dining room, and well-equipped kitchen. Guests can enjoy the expansive deck, covered porch, and firepit, as well as amenities like free Wi-Fi and a full kitchen with modern appliances.
9.6 7 reviews
Great Barrington, MA
07/26 – 08/04
$545/nighttotal: $4905 (9 )
The Race Mountain House
4 7
apartment , Sheffield
This Sheffield, Massachusetts mountain home sits near Mount Everett State Reservation (1.9 miles) and Mount Riga State Park (2.8 miles), offering easy access to hiking and outdoor recreation. This four-bedroom, three-bathroom vacation rental sleeps twelve, boasting a private pool, fireplace, fully equipped kitchen, in-house laundry, and a terrace – perfect for enjoying the stunning mountain views.
9.6 13 reviews
Great Barrington, MA
07/26 – 08/04
$1150/nighttotal: $10350 (9 )
Summer Chalet W/ Sparkling Pool In Great Barrington + Private Hiking Trails
4 7
apartment , Great Barrington
This secluded 4-bedroom, 3-bathroom cabin is located in the foothills of East Mountain, offering privacy and natural beauty just a short distance from the Great Barrington town center. This spacious accommodation accommodates up to 8 guests and features a seasonal swimming pool, private hiking trails connecting to the State Forest, expansive 30-foot ceilings with skylights, a wood-burning fireplace, and multiple outdoor areas for enjoying the Berkshires.
9.3 3 reviews
Great Barrington, MA
07/26 – 08/04
$692/nighttotal: $6228 (9 )
Berkshire House
1 7
apartment , Copake Falls
This 2-bedroom apartment offers a prime location at the base of the ski resort, just 5 miles from Hillsdale and Copake, NY, and Egremont, MA, with Great Barrington, MA, 15 miles away. This pet-friendly rental accommodates up to 7 guests with two queen beds and a bunk with trundle beds, featuring a full kitchen, air conditioning, and a garden, making it ideal for families seeking ski resort access and proximity to local towns.
10 8 reviews
Great Barrington, MA
07/26 – 08/04
$1598/nighttotal: $14382 (9 )
Stunning Renovated Victorian, Walk To Town
1 7
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.
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.
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.
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.
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.
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
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.
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.
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?
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
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.
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.
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.
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
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.
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.
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.
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.