The Berkshires, MA Vacation Homes from ￥9,593

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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.

￥60,177 total

includes taxes & fees

Nov 15 - Nov 16

A triangular-shaped building with a balcony and a wooden picnic table in front.

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

Sherwood Forest

Brian C.

￥57,429 total

includes taxes & fees

Nov 15 - Nov 16

A spacious living room with a wooden staircase, a dining area, and a television.

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

Sherwood Forest

William C B.

￥45,186 total

includes taxes & fees

Nov 18 - Nov 19

A cabin with a wooden deck and a stone pathway leading to the entrance.

4. Home in Great Barrington

Great Barrington

Janet G.

￥48,400 total

includes taxes & fees

Dec 13 - Dec 14

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

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

Housatonic

Eric H.

￥46,256 total

includes taxes & fees

Nov 14 - Nov 15

A picnic table in a grassy yard with trees and a fence in the background.

6. A Cozy Berkshire Escape l Close to the Slopes

Great Barrington

Kelly B.

￥47,560 total

includes taxes & fees

Nov 25 - Nov 26

7. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

￥78,701 total

includes taxes & fees

Nov 14 - Nov 15

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

8. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

￥65,371 total

includes taxes & fees

Nov 18 - Nov 19

A covered porch with string lights, a ceiling fan, and outdoor seating.

9. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

￥95,211 total

includes taxes & fees

Nov 16 - Nov 17

A rustic wooden building with a chimney, surrounded by lush greenery and flowering plants.

10. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

￥96,495 total

includes taxes & fees

Nov 16 - Nov 17

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

11. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

￥77,191 total

includes taxes & fees

Dec 4 - Dec 5

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

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

Stockbridge

Anonymous traveler

￥145,269 total

includes taxes & fees

Dec 14 - Dec 15

A modern kitchen with a granite countertop, stainless steel appliances, and a large island with drawers.

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

Great Barrington

Mary R.

￥106,543 total

includes taxes & fees

Nov 16 - Nov 17

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

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

￥75,509 total

includes taxes & fees

Nov 21 - Nov 22

A residential house with a blue exterior, a black fence, and a large tree in the background.

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

Williamstown

Michelle B.

￥87,392 total

includes taxes & fees

Nov 29 - Nov 30

A modern two-story house with a stone foundation, a covered porch, and a small shed.

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

Great Barrington

Roberta

￥190,120 total

includes taxes & fees

Nov 20 - Nov 21

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

￥203,487 total

includes taxes & fees

Nov 30 - Dec 1

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

18. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

￥174,424 total

includes taxes & fees

Nov 17 - Nov 18

A wooden swing set with two cushioned swings in a natural setting with trees and a cabin in the background.

19. Greylock Cabin

Florida

Margaret M.

￥75,538 total

includes taxes & fees

Dec 13 - Dec 14

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

20. All the comforts of home

Hudson

Julie B.

￥21,168 total

includes taxes & fees

Nov 17 - Nov 18

View all properties

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 wooden house with a porch, surrounded by trees and a body of water.

Prospect Berkshires

Egremont

10/10 Excellent

Emily

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

Anonymous traveler

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

A breakfast setting with a plate of food, a glass of orange juice, and a cup of tea.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe