A mountainous landscape with a lake and dense forests.

West Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for West Stockbridge vacation rentals

Outdoor dining

1. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
Stockbridge In-town Escape
Interior

2. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is SAR 657
SAR 1,199 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
4 bedrooms, travel crib, WiFi, bed sheets

3. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is SAR 1,909
SAR 3,277 total
includes taxes & fees
2 Sep - 3 Sep
Stylish Mid-century Modern Berkshires Cape
Smart TV

4. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is SAR 608
SAR 1,447 total
includes taxes & fees
15 Sep - 16 Sep
stylish Berkshires Retreat
Interior

5. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is SAR 718
SAR 1,129 total
includes taxes & fees
15 Sep - 16 Sep
Cozy Riverside Berkshires Retreat
Lobby

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,074 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is SAR 355
SAR 481 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Mountain Lodge
TV, fireplace, printers

7. 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, (7 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 SAR 2,136
SAR 4,939 total
includes taxes & fees
19 Aug - 20 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV, fireplace, DVD player, books

8. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is SAR 4,562
SAR 8,542 total
includes taxes & fees
14 Sep - 15 Sep
Berkshires farm, 30+ guests, 50 acres
Outdoor dining

9. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is SAR 999
SAR 2,102 total
includes taxes & fees
14 Sep - 15 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
Coffee/tea maker, fridge, microwave, oven

10. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is SAR 285
SAR 812 total
includes taxes & fees
19 Aug - 20 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Exterior

11. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is SAR 1,115
SAR 2,189 total
includes taxes & fees
13 Sep - 14 Sep
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Beach nearby, sun loungers, beach towels

12. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is SAR 837
SAR 1,183 total
includes taxes & fees
13 Sep - 14 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

13. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"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 SAR 1,517
SAR 2,512 total
includes taxes & fees
14 Sep - 15 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Coffee/tea maker, fridge, microwave, oven

14. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very Good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveler
The price is SAR 4,356
SAR 7,136 total
includes taxes & fees
23 Aug - 24 Aug
Renovated Downtown Great Barrington House
Coffee/tea maker, fridge, microwave, oven

15. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is SAR 1,014
SAR 1,527 total
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Coffee/tea maker, fridge, microwave, oven

16. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is SAR 389
SAR 581 total
includes taxes & fees
24 Aug - 25 Aug
Cozy 1-bedroom studio in serene Great Barrington with AC
Property grounds

17. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is SAR 939
SAR 1,539 total
includes taxes & fees
23 Aug - 24 Aug
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

18. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is SAR 818
SAR 2,128 total
includes taxes & fees
14 Sep - 15 Sep
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
TV, DVD player, books, video library

19. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is SAR 360
SAR 895 total
includes taxes & fees
14 Sep - 15 Sep
1800s Carriage house in Berkshires / Hudson Valley
TV

20. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is SAR 1,066
SAR 2,195 total
includes taxes & fees
16 Sep - 17 Sep
Treetop Hideaway in Tyringham
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"We loved the location, comfort, staff and all around feel of this sweet hotel for our visit to the Berkshires for a night at Tanglewood."
Deborah 1-night trip
Posted less than an hour ago
The Yankee Inn

Frequently asked questions

Can I find a vacation rental in West Stockbridge?

Yes, we have vacation rentals in West Stockbridge close to Hotchkiss Mobile Studio, or you can select a more secluded option if you want a relaxing stay. Visitors to West Stockbridge speak positively about the gardens and restaurants in this destination. Make sure you have time to check out the forests and lake views during your trip.

What are some of the best vacation home rentals that West Stockbridge has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This highly rated vacation home rental in West Stockbridge is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in West Stockbridge?

With 21 Expedia vacation rentals, you're sure to find just the right place for your West Stockbridge stay.

What can I see and do in West Stockbridge?

Family-friendly attractions include Hotchkiss Mobile Studio and Charles H. Baldwin & Sons, whereas Stockbridge Bowl is a spot to enjoy the outdoors. While here, Ebenezer II Gifts and Antiques and Hoffman's Pottery are other places worth a visit.

What are vacation rentals like in West Stockbridge?

Vacation rentals are privately owned accommodations you can stay in for several days or more in West Stockbridge. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.