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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for West Stockbridge vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,269 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is ￥12,263
￥17,266 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A covered porch with string lights, a ceiling fan, and outdoor seating.

2. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is ￥54,498
￥93,535 total
includes taxes & fees
Nov 17 - Nov 18
Secluded Family Home in Serene Stockbridge Woods
Indoor pool

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,844 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is ￥12,837
￥16,093 total
includes taxes & fees
Nov 15 - Nov 16
Vacation Village in the Berkshires
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is ￥27,981
￥46,256 total
includes taxes & fees
Nov 14 - Nov 15
Sweet Cozy Victorian in Housatonic. Close to everything.
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is ￥12,222
￥18,471 total
includes taxes & fees
Nov 19 - Nov 20
Cozy 1-bedroom studio in serene Great Barrington with AC
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

6. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (197 reviews)
"Great stay"
United States
George
The price is ￥13,176
￥14,758 total
includes taxes & fees
Nov 18 - Nov 19
Micosta Leisure Inn
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 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 ￥11,184
￥30,906 total
includes taxes & fees
Nov 16 - Nov 17
NEW RENO - Chalet-style farm loft near Tanglewood
A gazebo with a stone floor and a grassy area with trees in the background.

8. 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 ￥13,580
￥33,839 total
includes taxes & fees
Nov 17 - Nov 18
1800s Carriage house in Berkshires / Hudson Valley
A picnic table in a grassy yard with trees and a fence in the background.

9. A Cozy Berkshire Escape l Close to the Slopes

A Cozy Berkshire Escape l Close to the Slopes
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥32,353
￥47,560 total
includes taxes & fees
Nov 25 - Nov 26
A Cozy Berkshire Escape l Close to the Slopes
A covered outdoor seating area with two chairs and a view of a grassy landscape.

10. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is ￥35,948
￥46,221 total
includes taxes & fees
Nov 14 - Nov 15
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A rustic wooden building with a chimney, surrounded by lush greenery and flowering plants.

11. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is ￥50,759
￥96,495 total
includes taxes & fees
Nov 16 - Nov 17
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

12. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is ￥123,822
￥203,487 total
includes taxes & fees
Nov 30 - Dec 1
Beautiful and Private Home Centrally Located in the Berkshires
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

13. 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, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is ￥73,494
￥131,706 total
includes taxes & fees
Dec 7 - Dec 8
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A spacious living room with wooden beams, large windows, a chandelier, and a fireplace.

14. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
Luxury Barn Near Hudson With New Private Sauna
A sandy beach with a lake and forest in the background.

15. 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, (7 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 ￥33,392
￥51,933 total
includes taxes & fees
Nov 15 - Nov 16
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A white two-story house with a porch, surrounded by trees and a hill.

16. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (6 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 ￥25,902
￥65,030 total
includes taxes & fees
Nov 18 - Nov 19
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A cabin with a wooden deck and a stone pathway leading to the entrance.

17. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥31,978
￥48,400 total
includes taxes & fees
Dec 13 - Dec 14
Home in Great Barrington
A modern two-story house with a stone foundation, a covered porch, and a small shed.

18. 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, (10 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 ￥90,446
￥192,402 total
includes taxes & fees
Nov 20 - Nov 21
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A porch with two Adirondack chairs, a welcome mat, and a door labeled "Apartment 2".

19. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (6 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is ￥13,181
￥33,390 total
includes taxes & fees
Nov 15 - Nov 16
Berkshires Apartment at the Stephentown Hotel
A sign for East Rock Inn with a gravel path leading to a building surrounded by lush greenery.

20. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
The price is ￥50,663
￥58,731 total
includes taxes & fees
Nov 20 - Nov 21
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
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
"Breakfast was h asic everything else was perfect"
paul 2-night trip
Posted 14 hours ago
The Yankee Inn

Find out more about West Stockbridge

Search for holiday rentals in West Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in West Stockbridge using one of the methods below:

  • View our selection of featured holiday rentals in West Stockbridge
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Look no further and take a look at our great range of rental properties in West Stockbridge!

Frequently asked questions

Can I find a vacation rental in West Stockbridge?

Yes, we have vacation rentals in West Stockbridge close to Charles H. Baldwin & Sons, 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 20 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 Charles H. Baldwin & Sons and Ebenezer II Gifts and Antiques, whereas Stockbridge Bowl is a spot to enjoy the outdoors. Hoffman's Pottery and Berkshire Botanical Garden are a couple of places you'll find in the larger area.

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.