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$1,542 total

includes taxes & fees

9 Nov - 10 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$1,627 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$2,059 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$3,685 total

includes taxes & fees

29 Oct - 30 Oct

A patio area with wicker furniture and a brick floor.

5. The Old Avon 1800 Manor

Avon

Anonymous traveller

HK$3,525 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$2,305 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.

7. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

HK$2,836 total

includes taxes & fees

29 Oct - 30 Oct

A hot tub in a covered outdoor area with a view of trees and a fence.

8. Lakehaven • Hot Tub, Decks, Fires & More

Plymouth

Iva B.

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.

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

Sherwood Forest

Sharon K.

HK$2,942 total

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a sofa, coffee table, and a dining area with chairs.

10. #11 | Beds for 8, up to 14 with approval

Plainville

Neil R.

HK$4,519 total

includes taxes & fees

29 Oct - 30 Oct

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

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

Sherwood Forest

Frank M.

HK$2,990 total

includes taxes & fees

29 Oct - 30 Oct

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

12. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

HK$3,350 total

includes taxes & fees

2 Nov - 3 Nov

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

13. Home in Great Barrington

Great Barrington

Janet G.

HK$2,603 total

includes taxes & fees

9 Nov - 10 Nov

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

14. Treetop Hideaway in Tyringham

Monterey

Sarah B.

HK$4,403 total

includes taxes & fees

16 Nov - 17 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$5,555 total

includes taxes & fees

16 Nov - 17 Nov

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

16. Las Flores Villa

New Preston

HK$27,495 total

includes taxes & fees

30 Oct - 31 Oct

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Top Winsted Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"Staff were professional and friendly,"

Avon Old Farms Hotel

8/10 Good

"Avon Old Farms is in old property that has been very well maintained. It is charming, has comfortable seating throughout with small libraries for reading. It is light and airy. The breakfast that is provided as part of the room is adequate. The biggest negative is the staff, primarily the staff at the front desk. They are courteous but they do not extend themselves or demonstrate any warmth or enthusiasm that you are there. When you walk up, they say 'yes?' No "welcome to Avon Old Farms" or " I hope that your trip went well" or "if there's anything that we can do to make you stay more enjoyable, please let us know". They proceeded to perform the necessary check-in steps, answered my question about room service (not available) without adding any suggestions for dinner alternatives. Their attitude is that they're there because they have to be and that they are courteous and doing what they have to do to keep their jobs. That part was very disappointing. The rest of the hotel was charming, gracious, and I would stay there again in spite of the front office coolness."

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