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Compare 98 Cottages in West Stockbridge with updated reviews, rates, and availability.

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

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!
East Otis Vacation Rental | Studio | 1BA | 800 Sq Ft | Steps to Enter

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!
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Richmond Vacation Rental | 3BR | 2BA | Steps to Enter | 1,210 Sq Ft

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Private Lake Cottage on 3 acres w/350 sq. ft. deck
This living room has an oversized sectional with a large fireplace and smart TV.

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

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Cozy Berkshire cottage with fireplace.
Interior

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (23)
"Very good! Enjoyed every moment once we got the thermostat set to the right temp for us. Clean and cozy!"
Cozy Berkshire cottage with fireplace.
Welcome to the Red Bridge Cottage!
Cozy cottage with glass door pellet stove & whirlpool tub for those snowy nights

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!
The Blue Elm - A Historic Berkshire Cottage
Bathroom

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 750
SAR 1,542 total
includes taxes & fees
23 Feb - 24 Feb
The Blue Elm - A Historic Berkshire Cottage
Charming historic cottage on scenic road to Mt. Greylock
Summer

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (107)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Aerial view

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (11)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Family-Friendly Richmond Cottage w/ Private Yard
Richmond Vacation Rental | 2BR | 2BA | 1,750 Sq Ft | Stairs Required

Family-Friendly Richmond Cottage w/ Private Yard

2.0 star property
10.0 out of 10, Exceptional, (4)
"Comfortable. Homey. Very well stocked, especially the kitchen. Plenty of room and light. Thank you for our visit. "
Family-Friendly Richmond Cottage w/ Private Yard
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Stockbridge Vacation Rental | 4BR | 2BA | 1,700 Sq Ft | 3 Steps to Enter

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Lake Views & Dock Access - Pittsfield Cottage!
Pittsfield Vacation Rental | 4BR | 1.5BA | 2,000 Sq Ft | Step-Free Entry (Ramp)

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (1)
"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "
Lake Views & Dock Access - Pittsfield Cottage!
Quiet rustic cottage with shared lake access

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
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
The gorgeous view from our back yard and note the firepit!

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!
Beachwood Cottage
Exterior detail

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
Plan your Berkshires by the lake
Exterior

Plan your Berkshires by the lake

Plan your Berkshires by the lake
Fun Getaway Lakehouse in the Hudson Valley
Tiny house for glamping! Sleeps 2 and fire pit!

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (15)
"Can't say enough about this place. It looked like it was just recently built or renovated, and was very very clean. The place was warm, inviting, and very comfortable for my family of 5. Leticia is amazing, very very responsive and understanding. If you are staying in the area (the lake, skiing, etc.) I would highly recommend this place. We will definitely look to book this place again the next time we go skiing at Catamount."
Fun Getaway Lakehouse in the Hudson Valley
Cozy Hudson Valley Lake Cottage :CATAMOUNT SKI/SNOW BOARD
Relax on the large deck with lake views

Cozy Hudson Valley Lake Cottage :CATAMOUNT SKI/SNOW BOARD

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 :CATAMOUNT SKI/SNOW BOARD
Perfect Vacation Get Away - Historical New Marlborough
Exterior

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"Beautiful wrap-around porch. Views were wonderful. Had to use the pullout sofa, because the stairs to the loft was basically a stepladder and for us seniors, was a no go. It does need a microwave. We gave it a four star overall, but for a younger couple would be a five."
Perfect Vacation Get Away - Historical New Marlborough
Picturesque Cottage with Sunroom on Ashmere Lake!
Hinsdale Vacation Rental | 3BR | 2BA | 1,340 Sq Ft | Stairs Required

Picturesque Cottage with Sunroom on Ashmere Lake!

9.4 out of 10, Exceptional, (21)
"Everything was just like it was listed. We had trouble with the t.v. but other than that it was great. "
Picturesque Cottage with Sunroom on Ashmere Lake!
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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Other property types in West Stockbridge

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

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

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Wellspring by AvantStay | Indoor Pool + Views
Welcome!

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views
Vacation Village in the Berkshires
Exterior

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1765)
"Great place for a family vacation. Property very clean, quiet, and well organized "
The price is SAR 409
SAR 486 total
includes taxes & fees
3 Mar - 4 Mar
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 750 and SAR 750 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.