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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for West Stockbridge holiday homes

Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,367
HK$4,340 total
includes taxes & fees
5 Feb - 6 Feb
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Smart TV, books

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 reviews)
"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.
The price is HK$1,252
HK$3,082 total
includes taxes & fees
11 Feb - 12 Feb
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is HK$1,352
HK$2,225 total
includes taxes & fees
23 Feb - 24 Feb
Home in Great Barrington
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is HK$830
HK$1,104 total
includes taxes & fees
5 Feb - 6 Feb
All the comforts of home
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 reviews)
"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.
The price is HK$1,054
HK$2,094 total
includes taxes & fees
5 Feb - 6 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$937
HK$2,756 total
includes taxes & fees
24 Feb - 25 Feb
Near Tanglewood: Historic Summer Retreat
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is HK$1,406
HK$3,569 total
includes taxes & fees
8 Feb - 9 Feb
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
The price is HK$1,025
HK$2,069 total
includes taxes & fees
5 Feb - 6 Feb
Hudson Hot Tub & Pet Escape
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is HK$1,230
HK$3,127 total
includes taxes & fees
10 Feb - 11 Feb
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,476
HK$2,486 total
includes taxes & fees
17 Feb - 18 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,914
HK$11,005 total
includes taxes & fees
4 Mar - 5 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is HK$1,260
HK$4,009 total
includes taxes & fees
5 Feb - 6 Feb
Artists’ Hideaway in Old Chatham
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
The price is HK$1,367
HK$2,449 total
includes taxes & fees
5 Feb - 6 Feb
Renovated house. Built in 1890s. No neighbors in sight.
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (9 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,582
HK$2,325 total
includes taxes & fees
12 Feb - 13 Feb
Family Ski Getaway in the Berkshires
Smart TV, DVD player, books, stereo

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is HK$2,227
HK$4,084 total
includes taxes & fees
1 Mar - 2 Mar
Great Barrington Get Away
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,335
HK$5,078 total
includes taxes & fees
5 Feb - 6 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is HK$2,617
HK$4,900 total
includes taxes & fees
9 Feb - 10 Feb
Luxury Barn Retreat — All-Season Escape Awaits!
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$2,656
HK$4,589 total
includes taxes & fees
8 Feb - 9 Feb
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV

1 mile to Warren St.- Charming House in Hudson, NY

1 mile to Warren St.- Charming House in Hudson, NY
Hudson
The price is HK$1,953
HK$4,502 total
includes taxes & fees
5 Feb - 6 Feb
1 mile to Warren St.- Charming House in Hudson, NY
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,831
HK$8,874 total
includes taxes & fees
9 Feb - 10 Feb
Hancock Village Inn Near Jiminy Peak
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
"Spacious 2 bed 2 bath!"
Elaine 2-night trip
Posted 23 hours ago
Vacation Village in the Berkshires

Find out more about West Stockbridge

West Stockbridge Vacation Homes information

Number of reviews
201
Accommodation
480 Vacation Homes
Lowest Price
HK$1,104
Highest Price
HK$11,005

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