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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

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.
Treetop Hideaway In Tyringham - Great Barrington, MA
9.2 11 reviews

Treetop Hideaway In Tyringham

apartment, Tyringham
This secluded log cabin is located in Lee, offering expansive views of the Tyringham Valley and bordering conservation land in Monterey, a short drive from Greenock Country Club and Otis Ridge.
This spacious retreat features a recently renovated kitchen, a screened porch with a hot tub, a wraparound deck, and over 35 acres of private woods, accommodating up to 8 guests with 4 bedrooms and 1 bathroom.
Wilder House Berkshires - Great Barrington, MA
No reviews

Wilder House Berkshires

B&B, Sheffield
B&B rental. You will be based in Sheffield.
Services and facilities include an iron, a garden and a wheelchair friendly access. This accommodation in Sheffield also has a terrace!
Prime Location, Recently Redesigned, Riverfront! - Great Barrington, MA
10 1 review

Prime Location, Recently Redesigned, Riverfront!

apartment, Great Barrington
This historic factory conversion in Great Barrington is situated on the riverfront, offering 5-minute access to Butternut, 10-minute access to Catamount, and 30-minute access to Bousquet ski resorts, with nearby attractions including the Mahaiwe Performing Arts Center and the W.E.B. Du Bois Boyhood Homesite.
This spacious 2020 sq ft lodge accommodates up to 8 guests with 4 bedrooms, 2 bathrooms, a full kitchen, air conditioning, a terrace, garden, and onsite parking for 6 vehicles, featuring original historic elements like wood beams and stonework, along with two fireplaces and a grand piano.

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.

Historic Rectory Retreat In Stockbridge  Getaway For 8-12 Guests - Great Barrington, MA
10 14 reviews

Historic Rectory Retreat In Stockbridge Getaway For 8-12 Guests

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.
The Berkshire Mountain Inn - Great Barrington, MA
9.5 16 reviews

The Berkshire Mountain Inn

B&B, Great Barrington
This inn in Great Barrington is located 14 miles from Tanglewood and Cranwell Spa & Golf Club, and 9.3 miles from the Norman Rockwell Museum, with Great Falls and the Canaan Village Historic District also 12 miles away.
This B&B offers complimentary Wi-Fi, air-conditioned rooms, a garden, a terrace, and private parking, with check-out between 8:00 AM and 11:00 AM.
Idyllic Retreat; Hot Tub/sauna By Evergreen Home - Great Barrington, MA
10 43 reviews

Idyllic Retreat; Hot Tub/sauna By Evergreen Home

apartment, Great Barrington
This Great Barrington house rental, a private 3-bedroom, 3-bathroom home on 4.7 acres, is a 7-minute drive from downtown Great Barrington, 11 minutes from Lake Mansfield, and within easy reach of Butternut Ski Area, Lenox, and Tanglewood.
The 3-bedroom, 3-bathroom home boasts a spacious open-concept living area with a double-sided fireplace, a fully equipped kitchen, a hot tub, a sauna, a gym with a Peloton bike, and accommodates up to 8 guests comfortably.
Berkshires Retreat W Magic View! 
Beach/swim 1 Mi! - Great Barrington, MA
9.8 149 reviews

Berkshires Retreat W Magic View! Beach/swim 1 Mi!

apartment, Monterey
This Monterey apartment is located in the scenic Berkshires, a short drive from attractions like Ski Butternut, Great Barrington, and Jacob's Pillow. It offers a peaceful retreat in the woods with stunning views of Lake Garfield and surrounding mountains. The apartment has excellent user, location, and cleanliness ratings.
This 3-bedroom, 2-bathroom home has 1800 square feet of space and can comfortably accommodate 8 guests. The apartment features a fully equipped kitchen, high-speed Wi-Fi, a wood-burning stove, a private lake access, a deck with lounge chairs and a grill, and a fitness center.

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

1br+kitchenette|wifi|sleeps 4|ada|tanglewood - Great Barrington, MA
10 6 reviews

1br+kitchenette|wifi|sleeps 4|ada|tanglewood

apartment, Great Barrington
This charming bed and breakfast is located just outside of Great Barrington, a short drive from both the downtown area and the Butternut Ski Area. The surrounding area offers a peaceful and scenic setting, perfect for a relaxing getaway.
The suite comfortably accommodates up to four guests and features a fully equipped kitchen with a refrigerator and microwave, as well as air conditioning. Guests can enjoy mountain views, dedicated parking, and access to the entire property, including the newly renovated East Rock Inn.
Berkshires Retreat | Hiking & Swim | Fenced Yard - Great Barrington, MA
10 49 reviews

Berkshires Retreat | Hiking & Swim | Fenced Yard

apartment, Monterey
This Berkshire Mountains home, near Bear Town State Forest and Butternut Ski Area (7 minutes away) and Tanglewood (26 minutes away), offers easy access to other Berkshire attractions.
This five-bedroom, three-bathroom house sleeps ten, features a well-equipped kitchen with a 48-inch gas range and dual ovens, a private fenced backyard, multiple gathering areas, 1 GB fiber internet, and ample entertainment options including Roku TVs and arcade games.
The Hideaway: Berkshire Home - Village Of Egremont - Great Barrington, MA
9.9 147 reviews

The Hideaway: Berkshire Home - Village Of Egremont

apartment, Egremont
This Egremont apartment is located just outside of downtown Great Barrington, close to hiking, biking, shopping, skiing, and the arts. It consistently receives excellent ratings for location, cleanliness, and overall experience.
The apartment comfortably accommodates up to eight guests in its three bedrooms and two bathrooms. You'll find a fully equipped kitchen, a fireplace for cozy evenings, and access to the entire property, including a semi-finished basement with a ping pong table.
Stunning Renovated Victorian - Great Barrington, MA
10 59 reviews

Stunning Renovated Victorian

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.

Best Great Barrington, MA lodging with laundry available

Berkshires Family Inn  For Getaways & Big Groups! - Great Barrington, MA
9.7 74 reviews

Berkshires Family Inn For Getaways & Big Groups!

apartment, Great Barrington
This Great Barrington vacation home is located just 0.7 miles from Ski Butternut and within 3 miles of both Lake Buel and Beartown State Forest, making it a convenient base for exploring the area's natural beauty. Guests have consistently rated the property excellent in terms of location, cleanliness, and overall experience.
This 7-bedroom house comfortably accommodates up to 15 guests, making it perfect for large families or groups of friends. Amenities include a fully equipped kitchen, a fireplace, a garden, and parking, along with free Wi-Fi and a DVD player for entertainment.
King Bed|wi-fi|2m Ski Resort|studio - Great Barrington, MA
9.7 116 reviews

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

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.
Charming Idyllic Farmhouse Minutes To Great Barrington Ma And Salisbury Ct - Great Barrington, MA
10 37 reviews

Charming Idyllic Farmhouse Minutes To Great Barrington Ma And Salisbury Ct

apartment, Egremont
This 1740s farmhouse is located in South Egremont, a rural area in the Berkshires, minutes from downtown Great Barrington, local ski areas, and numerous attractions like Tanglewood, Jacobs Pillow, and Lime Rock Park. The property is a peaceful retreat surrounded by conservation land with walking trails, perfect for relaxation and recharging.
The farmhouse has 4 bedrooms, 3 bathrooms, and can accommodate up to 8 guests. You can enjoy a blend of historical charm and modern comfort with features like multiple fireplaces, a modern kitchen, a terrace overlooking a perennial garden and backyard pond, a greenhouse, picnic supplies, and more.
Riverside Retreat In The Berkshires - Great Barrington, MA
9.6 25 reviews

Riverside Retreat In The Berkshires

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.

Top 5-Star Lodgings in Great Barrington, MA

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

Condo ∙ 2 Bedrooms ∙ 6 Guests - Great Barrington, MA
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Lenox

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.

Newly Construced White House Set Back On A Knoll - Great Barrington, MA
10 36 reviews

Newly Construced White House Set Back On A Knoll

apartment, Great Barrington
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