Search Cottages in West Stockbridge

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 97 Cottages in West Stockbridge with updated reviews, rates, and availability.

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (104)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (22)
"We had a wonderful experience- house was clean and very comfy with all the amenities. Hosts went out of their way both before and during our stay to provide information and make sure all our needs were met! We enjoyed relaxing in the house and the location was also very close to many great Berkshires sights!! Highly recommend this listing! "
Cozy Berkshire cottage with fireplace.

Welcome to the Red Bridge Cottage!

10.0 out of 10, Exceptional, (1)
"Good experience. Love the front porch"
Welcome to the Red Bridge Cottage!

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough

Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!

9.8 out of 10, Exceptional, (6)
"Our family of four stayed here for the weekend after picking up our daughter from Hawthorne Valley Farm Camp, and this property was perfect for us! The home was immaculate and cool when we arrived. Rudy communicated a few days ahead of time about an issue with the fridge and provided coolers and ice for us to use. We loved eating dinner out on the porch and playing board games down in the media room. The beds were clean and comfortable without being too soft. It made a huge difference that our...
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is SAR 751
SAR 1,561 total
includes taxes & fees
2 Jan - 3 January 2025
The Blue Elm - A Historic Berkshire Cottage

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (103)
"I am originally from Western Mass, and was looking for a quiet get away for my fiancé and I for my birthday weekend. This more than fit the bill, we had many romantic nights in front of the fire (big y or tractor supply good for indoor wood). The cabin was delightful, quaint. And it was so quiet this time of year with no one else around us, which was just what I was looking for. Our hosts were great, made everything very easy for check in and check out and were easily valve through the App....
Quiet rustic cottage with shared lake access

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (14)
"Beautiful clean property. A lovely location. Exceeded expectations."
Fun Getaway Lakehouse in the Hudson Valley

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!

10.0 out of 10, Exceptional, (5)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"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."
Beachwood Cottage

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Modern Cozy Cottage, Games, Fireplace. 20 min to Hudson & Catamount Skiing

10.0 out of 10, Exceptional, (2)
"My family of four stayed at this house for a wedding in the area. The house was more than we expected. Very comfortable, good feel, and just an overall good experience."
Modern Cozy Cottage, Games, Fireplace. 20 min to Hudson & Catamount Skiing

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (37)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

A Charming Cottage - Secluded in Nature and Relaxing

10.0 out of 10, Exceptional, (3)
"The rental was nice. It was convenient for viewing the fall foliage and just enjoying the countryside. "
A Charming Cottage - Secluded in Nature and Relaxing

Waterfalls and Trails at 'the Mills At Green Hole'

3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
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.
Don't see what you're looking for?
See all available properties in West Stockbridge
Save an average of 15% on thousands of hotels when you're signed in

Other property types in West Stockbridge

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (8)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is SAR 704
SAR 810 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires
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.

Frequently asked questions

How much do cottages in West Stockbridge cost?
Cottages in West Stockbridge range between SAR 751 and SAR 751 per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in West Stockbridge with Expedia?
We think that a vacay should be hassle-free, so if you’re after cottages in West Stockbridge at an affordable price, Expedia has got you covered. Save those pennies and choose a low-cost option far from the downtown buzz, or book an upmarket cottage to really pamper your favorite people.
How can I find cheap cottages in West Stockbridge?
Expedia is here to help you look for cheap cottages in West Stockbridge. To reserve a fantastic stay in a couple of quick clicks, use the filter tool to refine your search results by star rating, budget and amenities.