The Berkshires Vacation Home Rentals from CA $86: Search Top Private Vacation Homes for Rent

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Our top choices for The Berkshires vacation homes

A hot tub with a string of lights above it, set against a dark night sky.

1. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

CA $534 total

includes taxes & fees

Nov 13 - Nov 14

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

2. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Brian C.

CA $510 total

includes taxes & fees

Nov 17 - Nov 18

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

3. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

CA $409 total

includes taxes & fees

Nov 26 - Nov 27

A house with a deck, a small garden, and a sunset in the background.

4. Home in Great Barrington

Great Barrington

Janet G.

CA $433 total

includes taxes & fees

Dec 13 - Dec 14

A dining area with a wooden table, chairs, and a ceiling fan.

5. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

CA $406 total

includes taxes & fees

Nov 13 - Nov 14

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

6. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Eric H.

CA $410 total

includes taxes & fees

Nov 13 - Nov 14

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

7. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

CA $580 total

includes taxes & fees

Nov 18 - Nov 19

8. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

CA $733 total

includes taxes & fees

Nov 13 - Nov 14

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

9. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

CA $872 total

includes taxes & fees

Nov 18 - Nov 19

A living room with a sofa, armchairs, a coffee table, and a television.

10. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

CA $817 total

includes taxes & fees

Nov 13 - Nov 14

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

11. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveller

CA $1,175 total

includes taxes & fees

Dec 7 - Dec 8

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

12. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

CA $946 total

includes taxes & fees

Nov 18 - Nov 19

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

13. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

CA $775 total

includes taxes & fees

Nov 29 - Nov 30

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

14. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

CA $1,716 total

includes taxes & fees

Nov 20 - Nov 21

A kitchen with white cabinets, a wooden dining table, and pendant lights.

15. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

CA $685 total

includes taxes & fees

Dec 4 - Dec 5

A wooden deck with a table and chairs, surrounded by a white railing.

16. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

CA $670 total

includes taxes & fees

Nov 13 - Nov 14

A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

17. Beautiful and Private Home Centrally Located in the Berkshires

West Stockbridge

CA $1,805 total

includes taxes & fees

Nov 18 - Nov 19

A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

18. Greylock Cabin

Florida

Margaret M.

CA $670 total

includes taxes & fees

Dec 13 - Dec 14

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

19. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

CA $1,555 total

includes taxes & fees

Nov 17 - Nov 18

A wooden deck with a staircase leading to a covered porch area.

20. All the comforts of home

Hudson

Julie B.

CA $188 total

includes taxes & fees

Nov 16 - Nov 17

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Learn more about The Berkshires

Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

See all hotels in The Berkshires

A large white building with multiple chimneys, surrounded by lush gardens with various flowers.

Top reviews in The Berkshires

A dining table with pastries, a coffee pot, and a vase of sunflowers.

Granville House

Housatonic

10/10 Excellent

Rebecca

A modern living room with a fireplace, large windows, and a cozy seating area.

Inn At Mount Snow

West Dover

10/10 Excellent

marco

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.

Lise