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12 Sep - 14 Sep
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19 Sep - 21 Sep
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3 Oct - 5 Oct
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31 Oct - 2 Nov

Cottages in West Stockbridge

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

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
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
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Property grounds

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (88)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"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 AED 735
AED 1,485 total
includes taxes & fees
4 Sep - 5 Sep
The Blue Elm - A Historic Berkshire Cottage
Perfect Vacation Get Away - Historical New Marlborough
Exterior

Perfect Vacation Get Away - Historical New Marlborough

9.2 out of 10, Wonderful, (57)
"Lovely place!"
The price is AED 551
AED 1,015 total
includes taxes & fees
1 Oct - 2 Oct
Perfect Vacation Get Away - Historical New Marlborough
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Outdoor dining

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

10.0 out of 10, Exceptional, (7)
"Very cozy, very nice views, tranquil, serene. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Private hot tub + Modern Cottage
Exterior

Private hot tub + Modern Cottage

9.8 out of 10, Exceptional, (7)
"The property had everything we needed. We enjoyed our stay immensely."
Private hot tub + Modern Cottage
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Outdoor dining

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

10.0 out of 10, Exceptional, (3)
"We were there for 2 nights for visiting day at a camp in the Berkshires. The home is very comfortable and clean. We enjoyed our stay! "
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
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
Charming historic cottage on scenic road to Mt. Greylock
Exterior

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (114)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Entire cottage in Berkshire Villiage
Exterior

Entire cottage in Berkshire Villiage

3.0 star property
9.8 out of 10, Exceptional, (6)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Exterior

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (7)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Exterior

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

9.4 out of 10, Exceptional, (13)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Berkshires farm, 30+ guests, 50 acres
Exterior

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is AED 4,004
AED 6,707 total
includes taxes & fees
21 Sep - 22 Sep
Berkshires farm, 30+ guests, 50 acres
Beachwood Cottage
Exterior

Beachwood Cottage

9.6 out of 10, Exceptional, (5)
"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
Vintage Country Home with Games, BBQ & Trails, & 20 Min to Hudson
Exterior

Vintage Country Home with Games, BBQ & Trails, & 20 Min to Hudson

10.0 out of 10, Exceptional, (3)
"My partner and I spent 5 wonderfully relaxing days exploring the small towns in the area, grilling out and enjoying being surrounded by so much natural beauty. The home is very clean and well equipped to make any stay comfortable. We are very much looking forward to planning our next visit."
Vintage Country Home with Games, BBQ & Trails, & 20 Min to Hudson
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Plan your Berkshires by the lake
Exterior

Plan your Berkshires by the lake

Plan your Berkshires by the lake
Quiet rustic cottage with shared lake access
Exterior

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (110)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
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 West Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Room was very clean. There is a lot to do at the property, 2 pools, activities for the kids. Lots of things to do in the area "
Judy 2-night trip
Posted 6 days ago
Vacation Village in the Berkshires

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Frequently asked questions

How much do cottages in West Stockbridge cost?
You can expect to pay between AED 551 and AED 4,004 per night for cottages in West Stockbridge. No matter your budget, the perfect stay is only a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in West Stockbridge with Expedia?
We think a getaway should be hassle-free, so if you're searching for cottages in West Stockbridge at a nice price, Expedia has got your back. Keep the budget under control and pick a low-cost option far away from the downtown buzz, or book an upscale cottage to really pamper your favorite people.
How can I find cheap cottages in West Stockbridge?
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