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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for West Stockbridge vacation rentals

Beach nearby

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"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."
United States
Christine P.
The price is ￥56,879
￥103,651 total
includes taxes & fees
Aug 6 - Aug 7
Beachwood Cottage
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,018 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is ￥23,972
￥30,422 total
includes taxes & fees
Aug 19 - Aug 20
Berkshire Mountain Lodge
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 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 ￥32,169
￥67,837 total
includes taxes & fees
Aug 3 - Aug 4
stylish Berkshires Retreat
Coffee/tea maker, fridge, microwave, oven

Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very Good, (1 review)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is ￥16,820
￥25,141 total
includes taxes & fees
Jul 30 - Jul 31
Cozy 1-bedroom studio in serene Great Barrington with AC
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (19 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 ￥36,329
￥55,465 total
includes taxes & fees
Aug 20 - Aug 21
Cozy Riverside Berkshires Retreat
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,464 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is ￥19,411
￥23,472 total
includes taxes & fees
Jul 29 - Jul 30
Vacation Village in the Berkshires
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (159 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is ￥21,785
￥24,400 total
includes taxes & fees
Jul 27 - Jul 28
Micosta Leisure Inn
Pool

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
The price is ￥22,360
￥45,030 total
includes taxes & fees
Jul 28 - Jul 29
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Gift shop

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is ￥19,242
￥41,000 total
includes taxes & fees
Jul 23 - Jul 24
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is ￥24,377
￥30,942 total
includes taxes & fees
Jul 27 - Jul 28
The Brooks Motel: Exceptional Suite
Exterior detail

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, (3 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 ￥46,515
￥99,806 total
includes taxes & fees
Aug 3 - Aug 4
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Gift shop

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is ￥19,242
￥41,000 total
includes taxes & fees
Jul 23 - Jul 24
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is ￥43,878
￥65,711 total
includes taxes & fees
Jul 29 - Jul 30
Home in Great Barrington
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 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 ￥52,816
￥82,412 total
includes taxes & fees
Aug 4 - Aug 5
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

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, (9 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 ￥37,377
￥61,701 total
includes taxes & fees
Aug 4 - Aug 5
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Gift shop

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is ￥22,523
￥45,212 total
includes taxes & fees
Jul 28 - Jul 29
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,942
￥21,493 total
includes taxes & fees
Jul 29 - Jul 30
All comforts of home
Coffee/tea maker, fridge, microwave, stovetop

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (5 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is ￥28,602
￥91,817 total
includes taxes & fees
Jul 27 - Jul 28
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Indoor pool

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is ￥19,242
￥41,000 total
includes taxes & fees
Jul 23 - Jul 24
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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
"The king deluxe suite was large enough for a family. The kitchen was sufficiently equipped to cook meals. The in room jacuzzi was comfortable for two. The outdoor pool was large and there were plenty of lounge chairs for the guests. The indoor pool was large as well, though a bit noisy. The views were very nice and the location is relatively close to Williams town, Pittsfield and Lenox. Lots of museums and other sights in the area. Overall a very nice location for long weekend or a full week."
Sharon 2-night trip
Posted 9 hours ago
Vacation Village in the Berkshires

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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  • Enter your travel dates to view the best deals on holiday rentals in West Stockbridge while they last

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 5 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 Hotchkiss Mobile Studio, 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.