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$1,885 total

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a bed, a nightstand, a lamp, a window with curtains, a television, and a bathroom door.

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

Collinsville

HK$1,294 total

includes taxes & fees

7 Oct - 8 Oct

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$2,060 total

includes taxes & fees

5 Oct - 6 Oct

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$4,125 total

includes taxes & fees

19 Oct - 20 Oct

A patio area with wicker furniture and a brick floor.

5. The Old Avon 1800 Manor

Avon

Anonymous traveller

HK$3,750 total

includes taxes & fees

20 Oct - 21 Oct

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$2,411 total

includes taxes & fees

5 Oct - 6 Oct

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

Will G.

HK$2,712 total

includes taxes & fees

12 Oct - 13 Oct

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$2,991 total

includes taxes & fees

7 Oct - 8 Oct

A living room with a sectional sofa, a small side table, and a floor lamp.

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

Plymouth

HK$6,783 total

includes taxes & fees

5 Oct - 6 Oct

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

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

Sherwood Forest

Frank M.

HK$3,078 total

includes taxes & fees

14 Oct - 15 Oct

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

11. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

HK$3,448 total

includes taxes & fees

12 Oct - 13 Oct

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

12. Home in Great Barrington

Great Barrington

HEATHER G.

HK$2,630 total

includes taxes & fees

26 Oct - 27 Oct

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

13. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

HK$4,537 total

includes taxes & fees

28 Oct - 29 Oct

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

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

Great Barrington

Mark M.

HK$5,565 total

includes taxes & fees

19 Oct - 20 Oct

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

15. Las Flores Villa

New Preston

HK$27,500 total

includes taxes & fees

16 Oct - 17 Oct

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Top Winsted Hotel Reviews

Extended Stay America Suites Hartford Farmington

8/10 Good

"The staff is very attentive."

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

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