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Compare 108 Cottages in Stockbridge with updated reviews, rates, and availability.

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (104)
"Great hosts who made our stay enjoyable. Very peaceful location. "
Quiet rustic cottage with shared lake access

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (11)
"Stayed with family for a wedding nearby and had a great experience. Nice house, clean and comfortable and as advertised. Very comfortable bed. Remote location so it’s quiet and peaceful, and short walk to lake. Host was very helpful and quick to respond. Would stay again!"
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (7)
"Beautiful home with a great location in the Berkshires. We had a wonderful time!"
East Otis Vacation Rental w/ Private Deck & BBQ!

Family-Friendly Richmond Cottage w/ Private Yard

2.0 star property
10.0 out of 10, Exceptional, (4)
"Excellent property: would have liked to stay longer. "
Family-Friendly Richmond Cottage w/ Private Yard

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (107)
"It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend."
Charming historic cottage on scenic road to Mt. Greylock

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is SAR 750
SAR 1,542 total
includes taxes & fees
27 Apr - 28 Apr
The Blue Elm - A Historic Berkshire Cottage

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (1)
"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "
Lake Views & Dock Access - Pittsfield Cottage!

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (37)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

10.0 out of 10, Exceptional, (2)
"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"2nd time here so I give it excellent review."
The price is SAR 563
SAR 1,053 total
includes taxes & fees
30 Apr - 1 May
Perfect Vacation Get Away - Historical New Marlborough

Picturesque Cottage with Sunroom on Ashmere Lake!

9.4 out of 10, Exceptional, (21)
"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (24)
"Very nice house. Owners very helpful."
Cozy Berkshire cottage with fireplace.

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Plan your Berkshires by the lake

Plan your Berkshires by the lake

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay with friends. Conveniently located near the water, great amenities and very clean. The host was incredibly responsive and kind throughout!"
Fun Getaway Lakehouse in the Hudson Valley

Cottage in the Clouds With Mountain Views

9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views
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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Other property types in Stockbridge

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (96)
"Very nice accommodation. Great location."
A Grand property in Historic Stockbridge

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1799)
"Always a great place to stay!!"
The price is SAR 348
SAR 422 total
includes taxes & fees
7 May - 8 May
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (928)
"Staff was exceptionally helpful and friendly."
The price is SAR 503
SAR 562 total
includes taxes & fees
25 Apr - 26 Apr
Jiminy Peak Mountain Resort
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.