Winsted Vacation Homes

A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.

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Our top choices for Winsted holiday homes

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

1. 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 modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.

2. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville

Brandon R.

HK$1,588 total

includes taxes & fees

4 Nov - 5 Nov

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

3. Sun Filled Lake House Living

Avon

Joseph C.

HK$1,965 total

includes taxes & fees

17 Nov - 18 Nov

A patio with a table and chairs, a grill, and a view of a lake.

4. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville

Mike

HK$3,654 total

includes taxes & fees

3 Nov - 4 Nov

A patio area with wicker furniture and a brick floor.

5. The Old Avon 1800 Manor

Avon

Anonymous traveller

HK$3,392 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Sherwood Forest

William C B.

HK$2,462 total

includes taxes & fees

16 Nov - 17 Nov

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

7. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

HK$2,720 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.

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

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

Sherwood Forest

Frank M.

HK$2,937 total

includes taxes & fees

4 Nov - 5 Nov

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

10. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

HK$3,192 total

includes taxes & fees

3 Nov - 4 Nov

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

11. Home in Great Barrington

Great Barrington

Janet G.

HK$2,497 total

includes taxes & fees

9 Nov - 10 Nov

A cozy cabin room with wooden walls, a bed, a sofa, and a window with curtains.

12. Treetop Hideaway in Tyringham

Monterey

Sarah B.

HK$4,212 total

includes taxes & fees

16 Nov - 17 Nov

A hot tub in a backyard with a house, trees, and a clear sky.

13. Las Flores Villa

New Preston

HK$11,217 total

includes taxes & fees

3 Nov - 4 Nov

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

14. Maya's Garden House

Great Barrington

HK$9,873 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Great Barrington

Mary R.

HK$5,231 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Great Barrington

HK$9,948 total

includes taxes & fees

15 Nov - 16 Nov

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Top Winsted Hotel Reviews

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent

"Very good place to stay"

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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