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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

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!
Interior

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

9.2 out of 10, Wonderful, (11)
"The cottage was adorable and spotless. Minutes to Great Barrington and Butternut and close to other Berkshire ski resorts. My family of 5 was so cozy and had plenty of space. The basement bedroom does get cold, especially the floor so bring your slippers!"
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
East Otis Vacation Rental w/ Private Deck & BBQ!
Desk, internet, bed sheets

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
Property grounds

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
Miscellaneous

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....
Outdoor dining

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
Outdoor dining

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
Exterior

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 AEDĀ 735
AEDĀ 1,485 total
includes taxes & fees
3 May - 4 May
The Blue Elm - A Historic Berkshire Cottage
Beachwood Cottage
Beach nearby

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
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Fridge, microwave, stovetop, dishwasher

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (1)
"This house was more than we could ask for itā€™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 didnā€™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
Paper towels

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!
Golf

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
Fridge, microwave, stovetop, dishwasher

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, itā€™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
Property grounds

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 AEDĀ 551
AEDĀ 1,019 total
includes taxes & fees
2 Jun - 3 Jun
Perfect Vacation Get Away - Historical New Marlborough
Picturesque Cottage with Sunroom on Ashmere Lake!
Interior

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 Ozzieā€™s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!
Cozy Berkshire cottage with fireplace.
Fridge, microwave, oven, stovetop

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
Dining

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
Exterior

Plan your Berkshires by the lake

Plan your Berkshires by the lake
Fun Getaway Lakehouse in the Hudson Valley
Terrace/patio

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
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

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1802)
"The property was clean and the staff very accommodated."
The price is AEDĀ 434
AEDĀ 525 total
includes taxes & fees
8 May - 9 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

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 AEDĀ 493
AEDĀ 550 total
includes taxes & fees
4 May - 5 May
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.