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

Best Great Barrington, MA lodging with a balcony

Cozy Riverside Berkshires Retreat - Great Barrington, MA
9.6 23 reviews

Cozy Riverside Berkshires Retreat

apartment, Great Barrington
This riverfront duplex in Great Barrington offers convenient access to downtown, Chesterwood, and the Mahaiwe Performing Arts Center, with outdoor cats on the property.
This 3-bedroom, 1-bathroom apartment accommodates up to 8 guests and features a full kitchen with a microwave, spa, parking, and internet, making it suitable for events and outdoor activities like skiing and sledding.
Superb Views  -- Sunsets, Mountains, Valley - Great Barrington, MA
10 17 reviews

Superb Views -- Sunsets, Mountains, Valley

apartment, Copake Falls
This apartment is located in Copake Falls, just outside the city center and adjacent to the Taconic State Park, with Catamount Ski Area 15 minutes away and Butternut Ski Area within close proximity. The apartment has an excellent user rating and offers a peaceful and secluded escape.
This spacious 2500-square-foot home can accommodate up to 8 guests and features 4 bedrooms and 3 bathrooms. The apartment offers a modern kitchen, a private pool, a tennis/pickleball court, a large lawn area, and a wrap-around deck with a large awning for shade.
Berkshires Mid-century Retreat! - Great Barrington, MA
No reviews

Berkshires Mid-century Retreat!

apartment, West Stockbridge
This West Stockbridge residence offers a unique mountain setting on 14 acres at the end of a dead-end road, providing immediate access to hiking trails just 2 minutes away and exceptional proximity to Tanglewood and Kripalu, both 5 minutes away. This 5-bedroom, 3-bathroom rental features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, terrace, garden, sauna, and parking, located 15 minutes from wineries, 10 minutes from museums, and 20 minutes from skiing.
Amore Estate -  Beautiful Room With Many Places To Explore And Relax In. - Great Barrington, MA
9.2 41 reviews

Amore Estate - Beautiful Room With Many Places To Explore And Relax In.

apartment, Lenox
This 6-bedroom apartment is located in Lenox, just a mile from the Lenox Center and 1.5 miles from Tanglewood, offering easy access to cultural events and attractions. Guests consistently rate this rental as excellent, praising its privacy, stunning views, and peaceful atmosphere.
This spacious home can comfortably accommodate up to 16 guests and features a wrap-around porch, a swimming pool, a sports court, and a garden. Guests can also enjoy fresh eggs from the on-site chickens and take advantage of the nearby hiking trails and natural beauty.

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.

Prime Location, Recently Redesigned, Riverfront! - Great Barrington, MA
9.8 9 reviews

Prime Location, Recently Redesigned, Riverfront!

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 South Lee Apt 2 Mi To Main Street - Great Barrington, MA
No reviews

Historic South Lee Apt 2 Mi To Main Street

apartment, Lee
This apartment is located in South Lee, a 5-minute walk from the Housatonic River and a 5-minute drive from the Naumkeag historical house.
This 1500 sq ft dwelling accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring air conditioning, a fireplace, on-site parking, and in-unit laundry.
Secluded 5bd Close To Best Of Berks - Great Barrington, MA
8.5 4 reviews

Secluded 5bd Close To Best Of Berks

apartment, Great Barrington
This spacious Berkshire County house, nestled in rolling fields with mountain and farm views, offers easy access to Great Barrington's attractions.
This five-bedroom, four-bathroom home sleeps ten, boasting a chef's kitchen, media room, children's playroom, and stunning countryside views; wildlife sightings are a possibility.
Farmhouse With Views  Nestled Among Nature Reserve - Great Barrington, MA
9.9 51 reviews

Farmhouse With Views Nestled Among Nature Reserve

apartment, Alford
This 18th-century farmhouse, located on a 24-acre estate in Alford, Massachusetts, near Mount Everett and a 900-acre nature preserve, offers a peaceful retreat. This four-bedroom, two-bathroom property sleeps eight guests and features high-speed internet, a fully equipped kitchen, and outdoor amenities including a mowed backyard, fern garden, and access to a 10-acre field.

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.

Popular destinations

Best Great Barrington, MA lodging with a kitchen

Historic Family Retreat On The At & Housatonic! - Great Barrington, MA
No reviews

Historic Family Retreat On The At & Housatonic!

apartment, Lee
This historic 1815 farmhouse apartment in South Lee is located along the Appalachian Trail, 2 miles from Stockbridge and 3 miles from downtown Lee, offering proximity to Ski Butternut (10 miles), Bousquet Mountain (12 miles), and Goose Pond Reservation & October Mountain State Forest (6 miles).
This 1500 square foot dwelling accommodates up to 5 guests with 3 bedrooms and 2 bathrooms, featuring a full kitchen with a fridge, microwave, and dishwasher, air conditioning, free WiFi, a washer/dryer, and parking, with mountain and river views available from the shared yard.
Stunning Summer Berkshires Retreat W/ Heated Pool - Great Barrington, MA
9.8 38 reviews

Stunning Summer Berkshires Retreat W/ Heated Pool

apartment, Egremont
This 4-bedroom apartment is located in the southern part of Berkshire County, just outside Great Barrington, minutes from historic towns, museums, and hiking trails. It has earned excellent ratings for user experience, location, and cleanliness.
The apartment can accommodate up to 8 guests and features a fully equipped kitchen, spacious living areas, multiple outdoor dining options, and a private garden. Enjoy amenities like air conditioning, a swimming pool, a Jacuzzi, and a terrace/balcony, along with a peaceful rural setting and abundant wildlife viewing opportunities.
Home With Pool On 10 Acres - Great Barrington, MA
10 2 reviews

Home With Pool On 10 Acres

apartment, Stockbridge
This Stockbridge condo offers a quiet country setting on serene wooded acreage, located 3 miles from Tanglewood.
This 1-bedroom, 2-bathroom rental accommodates up to 6 guests and features a newly renovated kitchen, central air conditioning, a private swimming pool, and a jacuzzi, with a caretaker on-site.
The Carriage House - A Lovely Apartment Rental - Great Barrington, MA
9.2 132 reviews

The Carriage House - A Lovely Apartment Rental

apartment, Great Barrington
This one-bedroom apartment is located in a carriage house on a hill just outside of downtown Great Barrington, a four-minute drive or a 15-minute walk from the town center. The apartment features a private deck, a well-equipped kitchen, and is ideal for couples seeking a peaceful and convenient retreat in the Berkshires.

Best Great Barrington, MA lodging with laundry available

Historic Home Featured In Berkshire Magazine - Great Barrington, MA
No reviews

Historic Home Featured In Berkshire Magazine

apartment, Great Barrington
This spacious Great Barrington home, located near local attractions, offers easy access to the town's amenities.
The 5,500-square-foot house boasts five bedrooms, four bathrooms, a fully fenced one-acre lot with a trampoline, ping pong table, basketball hoop, and an attic playroom, accommodating up to eight guests and featuring a game room, multiple patios, and a firepit.
Lakefront, Kayaks Included, Come Unwind In Lenox! - Great Barrington, MA
9.0 2 reviews

Lakefront, Kayaks Included, Come Unwind In Lenox!

apartment, Lenox
This newly renovated lakefront residence is located on Laurel Lake in Lenox, offering direct lakefront access and is within walking distance to The Mount (Edith Wharton's Home) and Shakespeare & Company, and a short drive to Tanglewood.
This 2150 square foot home features 4 bedrooms and 3 bathrooms, accommodating up to 10 guests with amenities including a chef's kitchen, wood-burning fireplace, enclosed 3-season porch with a foosball table, and a private dock for water activities.
Beautiful Private Country House - Great Barrington, MA
9.2 19 reviews

Beautiful Private Country House

apartment, West Stockbridge
This secluded West Stockbridge house, near Williamsville, is a 15-minute drive from both Lenox (Tanglewood) and Great Barrington, offering easy access to cultural attractions.
The two-bedroom, two-bathroom home comfortably sleeps three guests and features a king-size bed, jacuzzi tub, fully equipped kitchen, fast Wi-Fi, and a pull-out couch; a large DVD selection provides additional entertainment.
Hawthorne House - Great Barrington, MA
10 2 reviews

Hawthorne House

apartment, Stockbridge
This 3-bedroom, 2.5-bathroom Stockbridge condo offers convenient access, located down the road from Tanglewood and a short 5-mile drive to downtown Lenox, Lee, and Pittsfield.
This pet-friendly rental accommodates up to 7 guests with two living spaces, a full kitchen, a deck with a firepit, and private laundry, ideal for exploring the Berkshires.

Top 5-Star Lodgings in Great Barrington, MA

Discover the perfect blend of luxury and location with these sophisticated Great Barrington, MA homes.

Best Of The Berkshires + Hot Tub By Evergreen Home - Great Barrington, MA
9.9 154 reviews

Best Of The Berkshires + Hot Tub By Evergreen Home

apartment, Egremont

Best Dog-Friendly Lodgings in Great Barrington, MA

These dog-friendly short-term rentals in Great Barrington, MA ensure you'll find great trails nearby for you and your pup.

New Listing!!  Berkshire Flat Overlooking Rising Pond! - Great Barrington, MA
No reviews

New Listing!! Berkshire Flat Overlooking Rising Pond!

apartment, Great Barrington
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