Top Cottages in Berkshire County in 2026

Berkshire County Cottages
Massachusetts
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Berkshire County Hotels Vacation Rentals in Berkshire County Berkshire County Car Rentals Berkshire County Vacations

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

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Our top choices for Berkshire County cottages

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

A cozy cabin-style room with a white sofa, a small white table, and a fireplace.

A cabin with a wooden staircase leading to a deck, a covered area with a canoe, and a stone wall in the background.

A wooden cabin interior with a kitchen, a dining area, and a bathroom.

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.

A cozy attic room with a sloped ceiling, wooden beams, a ceiling fan, and a large window with a view of the outdoors.

A cozy dining area with a round table, chairs, and a hanging light fixture.

A wooden cabin with a steeply pitched roof, a porch with chairs, and a small shed nearby.

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)

9.0/10

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."

Monica

A-frame Cabin w/ Furnished Deck in Becket!

A covered deck with wicker chairs and a grill.

A log cabin interior with a dining area, a sofa, and a fireplace.

A wooden cabin interior with a dining area, kitchen, and living room.

A rustic cabin interior with a stone fireplace, wooden beams, and a dining area.

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)

6.0/10

(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."

Benjamin

Berkshire Hills Nature Lovers' Log Home Retreat

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

A sign for Balderdash Cellars with a wooden fence, a tree, and a parking lot in the background.

A modern kitchen with light grey cabinets, stainless steel appliances, and a large window providing a view of greenery.

A spacious living room with a fireplace, leather sofas, a coffee table, and a dining area with a table and chairs.

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)

10/10

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."

Carol

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

A cabin with a wooden deck, a staircase, and a small porch area.

A spacious living area with a wooden dining table, a sofa, and a kitchen area with a refrigerator and coffee maker.

A small, single-story cabin with a red door, a small porch, and a garden area.

A cozy living area with a striped sofa, a chandelier, and a wooden ceiling.

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.

A rustic cabin interior with a wooden desk, a bed, and a large abstract painting.

A rustic wooden interior with a large wooden table, a wooden staircase, and a brick fireplace.

A cozy cabin interior with large windows, wooden furniture, and a staircase.

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

A spacious living room with wooden beams, a large window, and a cozy seating area with a patterned rug.

A spacious room with wooden beams, a fireplace, a dining area with a table and chairs, and large windows.

A spacious living area with wooden beams, a fireplace, and a large window.

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.

A four-poster bed with a wooden headboard, a desk with a chair, and a large window with blinds.

A modern bathroom with a freestanding bathtub, a glass-enclosed shower, and a window with blinds.

A wooden staircase with a handrail, a bench, and a large window.

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.

A spacious living room with a white sofa set, a coffee table, and a view of a garden through large windows.

A covered patio with a round table, chairs, and a view of a forest.

A covered patio with large windows, a concrete base, and a grassy lawn.

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.

A cozy living room with a sofa, a coffee table, a lamp, and a framed botanical print on the wall.

An outdoor dining area with a wooden table and white chairs, surrounded by lush greenery and trees.

A dining area with a wooden table, white chairs, a brick column, a vase with sunflowers, and a basket with bread and tomatoes.

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)

10/10

Exceptional

(1 review)

"What a charming home! The bathrooms and bedrooms were updated beautifully. The downstairs was updated enough while keeping the character."

Mary

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

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

A wooden interior with a dining table, chairs, a fireplace, and large windows.

A spacious cabin with a large wooden dining table, comfortable seating, a fireplace, and large windows offering a view of the surrounding forest.

A rustic cabin interior with a wooden staircase, a dining area, and a living room furnished with a sofa and coffee table.

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)

2.0/10

(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...

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.

A spacious living room with a large window, a sofa set, a reading chair, and a television.

A modern living room with a grey sofa, a wooden chair, a fireplace, and a dining area in the background.

A modern bathroom with a freestanding bathtub, a glass-enclosed shower, and a skylight.

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.

A modern living room with a sectional sofa, a coffee table, and a red patterned rug.

A front door with a welcome mat, a hanging light fixture, and a stone pedestal.

A modern living room with grey sofas, a red patterned rug, and a fireplace.

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.

A modern kitchen with a central island, stainless steel appliances, wooden chairs, pendant lights, and a view of greenery outside.

A bedroom with a large bed, a television on a stand, and a view of the outdoors through large windows.

A modern living room with a fireplace, a sofa, a coffee table, and a large window.

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.

A bedroom with a large bed, two bedside lamps, a painting on the wall, and a window with curtains.

A covered outdoor seating area with wooden furniture and a view of a forested area.

A kitchen with a central island, four wooden chairs, a refrigerator, and various kitchen appliances.

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)

2.0/10

(1 review)

Cozy Stockbridge Cabin - Walk to Beach & Lake!

A living room with a grey sofa, a glass coffee table, a patterned rug, and a cabinet with glass doors.

A living room with a fireplace, a grey sofa, a blue armchair, and a patterned rug.

A modern kitchen with light wood cabinets, stainless steel appliances, and a green countertop.

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.

A boat docked on a sandy shore with a clear view of a lake and surrounding greenery.

A wooden cabin interior with a dining area, a large window overlooking a lake, and a poster on the wall.

A two-story house with a wooden deck and a staircase leading to the second floor.

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.

A cozy living room with a brown leather sofa, a round coffee table, and a small side table.

A modern bathroom with white subway tiles, a glass-enclosed shower, a marble countertop, and a wall-mounted light fixture.

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.

A living room with a sofa, coffee table, and TV stand.

A kitchen with wooden cabinets, a sink, and a stove. There is a door leading to another room.

A compact kitchen with wooden walls, a white countertop, a sink, a stove, and a door with a window.

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.

A wooden cabin with a large glass windowed porch, a dining table with chairs, and a sofa.

A wooden dock with a kayak and a chair by a calm lake, surrounded by lush greenery and hills.

A spacious wooden deck with a ceiling fan, a blue sofa, a table, and chairs.

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.

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Top Berkshire County Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"it was beautiful, centrally located, perfect getaway"

Tara 1-night trip

Posted 3 hours ago

Hotel Downstreet, an Ascend Collection Hotel

Hotel On North

10/10 Excellent

"This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night."

alan 1-night trip

Posted 12 hours ago

Hotel On North

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"no comment"

Thomas 1-night trip

Posted 12 hours ago

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"This hotel was clean and in a good location. The staff was friendly and helpful. I loved their nice pool and jacuzzi and enjoyed it. Breakfast was OK. Rooms are clean and big enough to make your money worth for it. One more important thing for us was its free and big parking lot."

Ramin 1-night trip

Posted 1 day ago

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Yankee Inn

10/10 Excellent

"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."

Mark 1-night trip

Posted 1 day ago

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Nice Inn/B&B in Lenox MA, about a mile from downtown."

Anne 1-night trip

Posted 1 day ago

The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

Joanne 1-night trip

Posted 2 days ago

The Red Lion Inn

Quality Inn Great Barrington

8/10 Good

"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."

Leslie 2-night trip

Posted 4 days ago

Quality Inn Great Barrington

Prospect Berkshires

10/10 Excellent

"Absolutely spectacular resort! Could not have enjoyed more."

Alexis 1-night trip

Posted 4 days ago

Prospect Berkshires

Find out more about Berkshire County

Berkshire County Cottages information

Number of reviews	6
Accommodation	60 Cottages
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South Lee Vacations
Frelinghuysen Morris House and Studio
Pleasant Valley Wilderness Sanctuary
Visit Lenox
Canoe Meadows Wildlife Sanctuary
Visit Lee
Kushi Institute
Lee Premium Outlets
Visit South Lee
Charles H. Baldwin & Sons
Crane Museum of Papermaking
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Lenox Mountain
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Greenock Country Club
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National Shrine of the Divine Mercy
Norman Rockwell Museum
Bousquet Ski Area
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Berkshire Botanical Garden
Pyramid Lake
Visit West Stockbridge

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Book Cottages in Berkshire County on Expedia.com

Cottages in Berkshire County

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Berkshire County cottages

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

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

3. Berkshire Hills Nature Lovers' Log Home Retreat

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

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

6. Serene Riverfront Stay! 'the Mill River Cabin

7. Luxury Vacation Rental in the Berkshires!

8. Spacious Historic Home in the Berkshires!

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

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

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

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

13. Water-view Home in the Berkshires

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

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

16. Stockbridge Home: Walk to Town Beach!

17. Picturesque Cottage With Sunroom on Ashmere Lake!

18. Whitney by Avantstay Private Berkshires Estate

19. Cozy Becket Cottage Escape w/ Lake Access!

20. Great Barrington Lakeside Getaway w/ Kayak & Grill

Find vacation rentals that suit your style

Top Berkshire County Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Find out more about Berkshire County

Berkshire County Cottages information

Explore a world of travel with Expedia