Sandisfield Vacation Homes

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Our top choices for Sandisfield holiday homes

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

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

Sherwood Forest

William C B.

HK$2,182 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Sherwood Forest

Frank M.

HK$2,937 total

includes taxes & fees

3 Nov - 4 Nov

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.

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

Sherwood Forest

Sharon K.

HK$2,802 total

includes taxes & fees

3 Nov - 4 Nov

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

4. Treetop Hideaway in Tyringham

Monterey

Sarah B.

HK$4,212 total

includes taxes & fees

16 Nov - 17 Nov

A wooden cabin interior with a bench, a rug, and a hanging plant.

5. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

Thomas C.

HK$1,432 total

includes taxes & fees

8 Nov - 9 Nov

A cozy living room with green sofas, a wooden ceiling, and a large window.

6. Maya's Garden House

Great Barrington

HK$9,873 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

7. Home in Great Barrington

Great Barrington

Janet G.

HK$2,497 total

includes taxes & fees

9 Nov - 10 Nov

A bathroom with a wooden vanity, a large mirror, and a shower with a glass door.

8. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

Great Barrington

HK$10,437 total

includes taxes & fees

14 Nov - 15 Nov

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

9. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

HK$3,192 total

includes taxes & fees

3 Nov - 4 Nov

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

10. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

HK$2,362 total

includes taxes & fees

3 Nov - 4 Nov

A house with a porch, a garden with pink flowers, and a stone wall along the road.

11. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

HK$2,720 total

includes taxes & fees

3 Nov - 4 Nov

A dining area with a wooden table, black chairs, and a vase with green plants.

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

Housatonic

Eric H.

HK$2,603 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Great Barrington

Mary R.

HK$5,231 total

includes taxes & fees

16 Nov - 17 Nov

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

HK$9,447 total

includes taxes & fees

4 Nov - 5 Nov

A wooden interior with a sectional sofa, a coffee table, and large windows offering a forest view.

15. Beautiful and Private Home Centrally Located in the Berkshires

West Stockbridge

HK$9,948 total

includes taxes & fees

9 Nov - 10 Nov

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

16. Spacious Central Berkshires Home for Groups

Lee

neil s.

HK$4,577 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Stockbridge

Anonymous traveller

HK$6,467 total

includes taxes & fees

23 Nov - 24 Nov

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

18. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

HK$4,820 total

includes taxes & fees

3 Nov - 4 Nov

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

19. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

HK$4,738 total

includes taxes & fees

15 Nov - 16 Nov

A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

20. Sun Filled Lake House Living

Avon

Joseph C.

HK$1,965 total

includes taxes & fees

17 Nov - 18 Nov

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Top Sandisfield Hotel Reviews

Berkshires Untold

10/10 Excellent

"We had a great stay. The lobby is beautiful- very warm and inviting. Don’t let the motel style fool you. The staff was very welcoming! Room was very spacious. We enjoyed sitting at the fire pit on a chilly fall night. Only suggestion would be softer pillows."

Quality Inn Great Barrington

10/10 Excellent

"This motel was exactly what we were looking for during our short stay. It was clean comfortable and easy to access. The bathroom toilet flushing mechanism was a bit slow/occasionally needed two flushes. There are train tracks behind the building and there is a train that will come by at night that is relatively loud. The breakfast had warm options and was satisfactory. Limited fresh fruit options but overall met our needs. I would stay here again and maybe request the front of the building to limit train noise."

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