A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Cottages in Berkshire County

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Berkshire County cottages

A wooden deck with outdoor seating and a view of a forest.

1. 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.

2. 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 a red railing, a covered grill, and a glass door leading to an interior space.

3. Berkshires Cabin 2 Mi to Appalachian Trail!

Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Otis
Berkshires Cabin 2 Mi to Appalachian Trail!
A covered porch with blue flooring, green chairs, and a small table.

4. Spacious Historic Home in the Berkshires!

Spacious Historic Home in the Berkshires!
3.0 star property
Pittsfield
Spacious Historic Home in the Berkshires!
A rustic cabin with a red exterior, a wooden deck, and a stone wall.

5. 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 two-story house with a front porch, a brick chimney, and a well-maintained garden.

6. 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 furniture, a shaded area, and a view of trees and a house.

7. 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 wooden deck with Adirondack chairs, a glass door, and a brick wall.

8. 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 modern room with a glass table, chairs, a sofa, and a view of a forest.

9. Water-view Home in the Berkshires

Water-view Home in the Berkshires
3.0 star property
Sheffield
Water-view Home in the Berkshires
A white house with a symmetrical roof and a central chimney, surrounded by a well-maintained lawn and dense forest.

10. Whitney by Avantstay Private Berkshires Estate

Whitney by Avantstay Private Berkshires Estate
3.0 star property
Sheffield
Whitney by Avantstay Private Berkshires Estate

11. Luxury Vacation Rental in the Berkshires!

Luxury Vacation Rental in the Berkshires!
3.0 star property
Williamstown
Luxury Vacation Rental in the Berkshires!
A wooden deck with two red chairs and a table, overlooking a forested area with a stream.

12. 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
A wooden deck with outdoor seating and a glass door leading to a room.

13. 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 park with a lake, benches, and boats.

14. Stockbridge Home: Walk to Town Beach!

Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge
Stockbridge Home: Walk to Town Beach!
A covered outdoor area with a table and chairs, large windows, and a view of a lake and forest.

15. 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 deck with a table and chairs, overlooking a lake with boats and a dock.

16. 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 two-story house with a large lawn, a covered patio, and a view of the surrounding forest.

17. 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 wooden deck with outdoor seating, overlooking a river and autumn foliage.

18. 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
A modern house with a large deck, surrounded by a forest.

19. 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 deck with wicker furniture and a potted plant, surrounded by a wooden railing and a house with large windows.

20. 1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
3.0 star property
Glendale
10.0 out of 10, Exceptional, (1 review)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
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 Berkshire County Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"the good….full kitchen, living room, king bedroom, clean bathroom, VERY reasonable nightly rate, especially for central berkshire county in the summer. there is no daily room cleaning, but extra towels, etc are always available from the front desk… the less than good…we’ve stayed here now u time in the past 18 months, but the last couple of stays the rooms have been a little musty and damp, despite (or because of?) the a/c being on constantly. ya gotta hold the handle down on the toilet to get a complete flush. no food service, but the is a stop&shop literally across the street… i would still recommend BML for the room rate and location alone…"
Barry 2-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

Find out more about Berkshire County

Berkshire County Cottages information

Number of reviews
6
Accommodation
61 Cottages
Lowest Price
Highest Price