A historic building with a tall tower, surrounded by lush green trees and a well-maintained lawn.

Cottages in Berkshire County

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Berkshire County cottages

A rustic cabin with a red exterior, a wooden deck, and a stone wall.

1. Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
3.0 star property
Great Barrington
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
A wooden deck with outdoor seating and a view of a forest.

2. A-frame Cabin w/ Furnished Deck in Becket!

A-frame Cabin w/ Furnished Deck in Becket!
3.0 star property
Becket
9.0 out of 10, Wonderful, (2 reviews)
"This cabin has absolutely everything you can think of!! Shampoo, conditioner, pots and pans, cutlery, towels, bug spray, firewood, fans, AC, even a car charger!! I was a little worried because I didn’t connect with the property manager but I had received all the check in information I needed. Absolutely no worries needed! Check in and check out was totally seamless."
United States
Monica
A-frame Cabin w/ Furnished Deck in Becket!
A covered deck with wicker chairs and a grill.

3. Berkshire Hills Nature Lovers' Log Home Retreat

Berkshire Hills Nature Lovers' Log Home Retreat
3.0 star property
Windsor
6.0 out of 10, (1 review)
"Loved home, view and area. Did not love ac only on lower level. It was 82 in sleeping areas at 10pm when we arrived and stayed hot."
United States
Benjamin
Berkshire Hills Nature Lovers' Log Home Retreat
A wooden deck with Adirondack chairs, a glass door, and a brick wall.

4. 3 Acres, Mtn Views, Hot Tub, Steps to Winery

3 Acres, Mtn Views, Hot Tub, Steps to Winery
3.0 star property
Richmond
10.0 out of 10, Exceptional, (1 review)
"This home is exceptional in all respects --beautifully situated on lovely property, well located in southern Berkshires. Newly remodeled. Great outdoor space. Fabulous kitchen with new appliances, extremely well-outfitted. Host easily accessible. Exceeded all expectations. Would definitely return if plans allow."
United States
Carol
3 Acres, Mtn Views, Hot Tub, Steps to Winery
A cabin with a wooden deck, a staircase, and a small porch area.

5. East Otis Vacation Rental w/ Private Deck & Bbq!

East Otis Vacation Rental w/ Private Deck & Bbq!
3.0 star property
Otis
East Otis Vacation Rental w/ Private Deck & Bbq!
A wooden deck with two red chairs and a table, overlooking a forested area with a stream.

6. Serene Riverfront Stay! 'the Mill River Cabin

Serene Riverfront Stay! 'the Mill River Cabin
3.0 star property
Mill River
Serene Riverfront Stay! 'the Mill River Cabin
Interior

7. Luxury Vacation Rental in the Berkshires!

Luxury Vacation Rental in the Berkshires!
3.0 star property
Williamstown
Luxury Vacation Rental in the Berkshires!
A covered porch with blue flooring, green chairs, and a small table.

8. Spacious Historic Home in the Berkshires!

Spacious Historic Home in the Berkshires!
3.0 star property
Pittsfield
Spacious Historic Home in the Berkshires!
A two-story house with a large lawn, a covered patio, and a view of the surrounding forest.

9. Modern Berkshires Farmhouse w/ Porch, Fireplace & Views Beaver Creek by Avantstay

Modern Berkshires Farmhouse w/ Porch, Fireplace & Views Beaver Creek by Avantstay
3.0 star property
Stockbridge
Modern Berkshires Farmhouse w/ Porch, Fireplace & Views Beaver Creek by Avantstay
A two-story house with a front porch, a brick chimney, and a well-maintained garden.

10. Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
3.0 star property
Lee
10.0 out of 10, Exceptional, (1 review)
"What a charming home! The bathrooms and bedrooms were updated beautifully. The downstairs was updated enough while keeping the character."
United States
Mary
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
A wooden deck with outdoor seating and a glass door leading to a room.

11. Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.0 star property
Great Barrington
2.0 out of 10, (1 review)
"Pictures do not reflect the present condition of the cabin which has deteriorated over time and has not been properly maintained. The cabin had cobwebs in every corner of the house. The couch on dirty and the cushions are stained. The bathroom tub was moldy. The refrigerator was dirty and there was a hole in the living room ceiling, a hole open to the outside in the bathroom window frame. There was snow everywhere that we could use the front door, the patio, the BBQ or the Firepit. We...
United States
Joe
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
A covered outdoor area with a table and chairs, large windows, and a view of a lake and forest.

12. Lakefront Otis Home w/ Stunning Views & Boats!

Lakefront Otis Home w/ Stunning Views & Boats!
3.0 star property
Otis
Lakefront Otis Home w/ Stunning Views & Boats!
A modern room with a glass table, chairs, a sofa, and a view of a forest.

13. Water-view Home in the Berkshires

Water-view Home in the Berkshires
3.0 star property
Sheffield
Water-view Home in the Berkshires
A modern house with a large deck, surrounded by a forest.

14. Secluded + Modern Enclosed Patio, Forest Views Woodland Zen by Avantstay

Secluded + Modern Enclosed Patio, Forest Views Woodland Zen by Avantstay
3.0 star property
Housatonic
Secluded + Modern Enclosed Patio, Forest Views Woodland Zen by Avantstay
A wooden deck with outdoor furniture, a shaded area, and a view of trees and a house.

15. Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake!
3.0 star property
Stockbridge
2.0 out of 10, (1 review)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
A park with a lake, benches, and boats.

16. Stockbridge Home: Walk to Town Beach!

Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge
Stockbridge Home: Walk to Town Beach!
A deck with a table and chairs, overlooking a lake with boats and a dock.

17. Picturesque Cottage With Sunroom on Ashmere Lake!

Picturesque Cottage With Sunroom on Ashmere Lake!
3.0 star property
Hinsdale
Picturesque Cottage With Sunroom on Ashmere Lake!
A white house with a symmetrical roof and a central chimney, surrounded by a well-maintained lawn and dense forest.

18. Whitney by Avantstay Private Berkshires Estate

Whitney by Avantstay Private Berkshires Estate
3.0 star property
Sheffield
Whitney by Avantstay Private Berkshires Estate
A wooden deck with a table and chairs, a window, and a view of the forest.

19. Cozy Becket Cottage Escape w/ Lake Access!

Cozy Becket Cottage Escape w/ Lake Access!
3.0 star property
Sherwood Forest
Cozy Becket Cottage Escape w/ Lake Access!
A wooden deck with outdoor seating, overlooking a river and autumn foliage.

20. Great Barrington Lakeside Getaway w/ Kayak & Grill

Great Barrington Lakeside Getaway w/ Kayak & Grill
3.0 star property
Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Berkshire County Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"This is a gem of a small hotel/motel. Super comfortable rooms, updated bathrooms, and well done self serve breakfast included. Also has an indoor pool and an outdoor pool during the season. And a very nice hiking trail off of the back. An excellent change from the Run of the middle courtyard Marriott!"
Kimberly 2-night trip
Posted less than an hour ago
The Yankee Inn

Find out more about Berkshire County

Berkshire County Cottages information

Number of reviews
6
Accommodation
61 Cottages
Lowest Price
Highest Price