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Compare 414 Vacation Homes in Great Barrington with updated reviews, rates, and availability.

Exterior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (183)
"We rented the house to celebrate mom’s 70th birthday. We wanted a quiet, simple place where we could spend time together, visit, and spend time outdoors. That’s exactly what we got. We all fished and kayaked and enjoyed the peaceful scenery. Thank you."
Peace and quiet on the lake
Property grounds
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Front of home
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (17)
"The property was perfect for our needs. Instructions for everything was provided fabulous rental. "
Newly Renovated Family House On Highland Lake with Dock
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Exterior
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (64)
"This is the 2nd time we've stayed here and loved it again. This has become our go to place to stay for our Berkshires adventures. Clean, comfortable, beautiful, private (the garden center was not open while we were there in Feb.), and great location!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior
Hilltown Nest is a wonderful place for family and friends to gather.
10.0 out of 10, Exceptional, (12)
"We had a great time. Owner was great about responding to questions. Very comfortable."
Hilltown Nest is a wonderful place for family and friends to gather.
Exterior
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Welcome!
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (119)
"My wife and I and our daughter and dog spent the week. Everything we needed was provided. Nice quiet and relaxing time. Great location down the street from the AMC Noble View trails. We all had a wonderful hike and a wonderful week."
The price is AED 790
AED 1,413 total
includes taxes & fees
22 May - 23 May
Big farmhouse in the foothills of the Berkshires
Living area
Near Tanglewood: Historic Summer Retreat
9.2 out of 10, Wonderful, (7)
"Visit was for a family gathering in the neighboring town. House was very comfortable and perfect for my needs. Amanda was available for my questions."
The price is AED 588
AED 1,369 total
includes taxes & fees
22 May - 23 May
Near Tanglewood: Historic Summer Retreat
Dining
Sweet Cozy Victorian in Housatonic. Close to everything.
The price is AED 643
AED 1,079 total
includes taxes & fees
23 May - 24 May
Sweet Cozy Victorian in Housatonic. Close to everything.
Renovated 9-BR 1800s Inn 8-Min to Catamount
Renovated 9-BR 1800s Inn 8-Min to Catamount
Room
Bright, Airy Home with TONS of character in Hudson, NY - 5 min from Warren St
8.4 out of 10, Very Good, (9)
"Stayed to go to nearby wedding. Wished we had more time to enjoy the house and very nice yard and fire pit. Bagel place a mile down the road is very nice and good!"
The price is AED 698
AED 1,146 total
includes taxes & fees
20 May - 21 May
Bright, Airy Home with TONS of character in Hudson, NY - 5 min from Warren St
Dancing Horse Lodge - Entrance View
Dancing Horse Lodge
9.4 out of 10, Exceptional, (29)
"My daughters and I really enjoyed our stay at Dancing Horse Lodge and would love to stay again! It's a great location - close to great stores and restaurants, so even though it rained for most of our stay there was plenty to still do. And then our time on property was relaxing and had everything we needed! Definitely enjoyed the gas fireplace, and our accommodations were very comfortable! Hoping to book another trip here late summer/early Fall."
Dancing Horse Lodge
Athens Vacation Rental | 3BR | 3BA | 2,800 Sq Ft | Steps Required to Enter
Stunning Athens Home: Grill, Fire Pit, Pool Access
6.0 out of 10, (2)
Stunning Athens Home: Grill, Fire Pit, Pool Access
Kitchen and dining room
Hudson Valley and The Berkshires getaway
10.0 out of 10, Exceptional, (1)
"Overnight golf trip with cousins and father. Perfect accommodations not far from the copake country club. Great time"
Hudson Valley and The Berkshires getaway
Classic Stockbridge Cottage
9.8 out of 10, Exceptional, (7)
"Good but steep driveway and steps"
The price is AED 2,564
AED 5,484 total
includes taxes & fees
26 May - 27 May
Classic Stockbridge Cottage
Breathtaking Mountain Views.
Mountain View Getaway
10.0 out of 10, Exceptional, (35)
"Couldn’t ask for better hosts! The house is impeccable and the views are amazing!"
Mountain View Getaway
Tranquil Victorian on Charming Street
The price is AED 1,286
AED 2,097 total
includes taxes & fees
19 May - 20 May
Tranquil Victorian on Charming Street
Berkshires Manor
Berkshire Manor for Lasting Memories
10.0 out of 10, Exceptional, (1)
"Escape to the serene New England Berkshires with a stay at Lee Manor, located just a short drive from the highway and within walking distance of the charming town of Lee. Surrounded by endless activities and with ample outdoor space and convenient on-site parking, this beautiful home is the perfect retreat. Mary and Leah, the hosts of Lee Manor, are exceptional. Their communication is flawless, with helpful messages filled with local information and recommendations before your arrival. Whenever...
Berkshire Manor for Lasting Memories
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Great Barrington

Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Great Barrington Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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