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Vacation Homes in Great Barrington

Spacious Home nestled along the Blackberry River in Northwest CT
Fridge, microwave, oven, stovetop

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT
Charming cottage with lake access, wood burning fire place, and WiFi
Smart TV, fireplace

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (8)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (128)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds
Property grounds

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (4)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is ￥14,572
￥19,565 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is ￥29,438
￥53,520 total
includes taxes & fees
Aug 18 - Aug 19
Big farmhouse in the foothills of the Berkshires
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Terrace/patio

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (5)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Property grounds

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great stay. The host was great with communicating directions and details for the home and even shared local recommendations. We appreciated their quick response to our questions, too. "
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Relax or be active! The choice is yours in this pet-friendly family home.
Fridge, microwave, oven, stovetop

Relax or be active! The choice is yours in this pet-friendly family home.

9.8 out of 10, Exceptional, (14)
"Home was exactly as listed, very comfortable and convenient for my family’s trip. "
Relax or be active! The choice is yours in this pet-friendly family home.
Falls Reach In The Heart of Copake
Property grounds

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake
Stylish Pine Plains Home Near Parks & Hiking!
Fridge, microwave, stovetop, dishwasher

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (16)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
Woodland A-Frame
Interior

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Poolside Luxe at Long Pond
Exterior

Poolside Luxe at Long Pond

Poolside Luxe at Long Pond
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is ￥34,148
￥72,535 total
includes taxes & fees
Aug 18 - Aug 19
Near Tanglewood: Historic Summer Retreat
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Charming 3-bedroom house with WiFi, AC in delightful Hudson
Microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in delightful Hudson

2.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed our stay. The house was spacious for 4 adults and 1 baby. We were here for a wedding so we spent a lot of time in town rather than in the home/kitchen. The house is very conveniently located a couple blocks from the middle of the main strip (Warren St). 2 of the 3 beds were comfortable! "
Charming 3-bedroom house with WiFi, AC in delightful Hudson
Quiet Cabin On Over 12 Acres Of Woods!
Interior

Quiet Cabin On Over 12 Acres Of Woods!

10.0 out of 10, Exceptional, (12)
"Very nicely appointed and well equipped cabin in a quiet, rustic setting. Close to the towns of Stockbridge and Lee. Perfect for a Berkshire get away. "
Quiet Cabin On Over 12 Acres Of Woods!
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires
Interior

Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

2.0 star property
10.0 out of 10, Exceptional, (6)
"A very good place to stay. Best of all, each bedroom has its own bathroom. There's plenty of hot water, even if multiple people are showering at the same time. The only downside to me is that the washer is broken when we checked in. We want to come again!"
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires
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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Top Great Barrington Hotel Reviews

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

10/10 Excellent
"it was very quiet"
Ruth 1-night trip
Posted 2 days ago
Travelodge by Wyndham Great Barrington Berkshires