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Vacation Homes in West Stockbridge

Near Tanglewood: Historic Summer Retreat

New Lebanon
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
United States
Patty W.
$373 nightly
The price is $418
Nov 11 - Nov 12
Total with taxes and fees
Near Tanglewood: Historic Summer Retreat

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$338 nightly
The price is $377
Nov 12 - Nov 13
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

All the comforts of home

Hudson
9.2 out of 10, Wonderful, (27)
"Peaceful, friendly, clean, wish I had more time to explore and hope to return one day! Thank you!!"
United States
Barbara V.
$126 nightly
The price is $141
Nov 11 - Nov 12
Total with taxes and fees
All the comforts of home

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (40)
"we had a wonderful time staying at the house, very comfortable and well equipped and responsive host."
United States
lisa s.
$404 nightly
The price is $451
Nov 11 - Nov 12
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
United States
Kaye S.
$332 nightly
The price is $372
Dec 1 - Dec 2
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$351 nightly
The price is $392
Nov 11 - Nov 12
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
$217 nightly
The price is $242
Nov 13 - Nov 14
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
$244 nightly
The price is $272
Dec 1 - Dec 2
Total with taxes and fees
Home in Great Barrington

Hudson Hot Tub & Pet Escape

2.0 star property
Stottville
$279 nightly
The price is $282
Nov 11 - Nov 12
Total with taxes and fees
Hudson Hot Tub & Pet Escape

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
$464 nightly
The price is $518
Nov 11 - Nov 12
Total with taxes and fees
Great Barrington Get Away

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
$533 nightly
The price is $540
Nov 11 - Nov 12
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$440 nightly
The price is $492
Nov 12 - Nov 13
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$252 nightly
The price is $282
Nov 12 - Nov 13
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"Great location, very clean and well appointed with everyth"
United States
Nick R.
$345 nightly
The price is $385
Nov 30 - Dec 1
Total with taxes and fees
Bungalow in the Berkshires

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
10.0 out of 10, Exceptional, (56)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
$480 nightly
The price is $538
Nov 11 - Nov 12
Total with taxes and fees
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
$573 nightly
The price is $622
Dec 6 - Dec 7
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Hudson
10.0 out of 10, Exceptional, (1)
"Perfect Hudson Valley Girls weekend! The house was gorgeous, so incredibly clean, comfortable beds, beautiful outdoor fire pit area with jacuzzi overlooking the river. All the little efforts were put into the property to make it feel like an intimate home, like providing plenty of additional towels for the jacuzzi, shampoo / conditioner in the showers and more. We were able to spend each day in Hudson downtown enjoying all the boutiques and restaurants because it was such an easy drive into...
United States
Caitlin W.
$636 nightly
The price is $712
Nov 11 - Nov 12
Total with taxes and fees
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Awesome place to stay to ski for the weekend. Skiing on and off was very easy, quick ride to dinner and plenty of room in the condo for everyone. Can’t wait to come back!"
United States
Christine L.
$490 nightly
The price is $547
Nov 11 - Nov 12
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Artists’ Hideaway in Old Chatham

Old Chatham
$421 nightly
The price is $472
Nov 12 - Nov 13
Total with taxes and fees
Artists’ Hideaway in Old Chatham

1BR Hudson Apartment, 3Min Walk To Warren St For Two - Apartment 1 - Pet Allowed

Hudson
$338 nightly
The price is $382
Nov 16 - Nov 17
Total with taxes and fees
1BR Hudson Apartment, 3Min Walk To Warren St For Two - Apartment 1 - Pet Allowed
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

Find out more about West Stockbridge

West Stockbridge Vacation Homes information

Number of reviews
313
Accommodation
493 Vacation Homes
Lowest Price
$141
Highest Price
$712

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