Winsted, CT Vacation Homes from AED 774

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 vacation 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.

AED 774 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

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

Collinsville

Judy L.

AED 811 total

includes taxes & fees

2 Nov - 3 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.

AED 992 total

includes taxes & fees

20 Oct - 21 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

AED 1,795 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 traveler

AED 1,651 total

includes taxes & fees

20 Oct - 21 Oct

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

6. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

AED 1,320 total

includes taxes & fees

22 Oct - 23 Oct

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

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

Sherwood Forest

William C B.

AED 1,169 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Plymouth

Iva B.

AED 2,850 total

includes taxes & fees

18 Oct - 19 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.

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

Sherwood Forest

Sharon K.

AED 1,378 total

includes taxes & fees

27 Oct - 28 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.

AED 1,445 total

includes taxes & fees

28 Oct - 29 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.

AED 1,577 total

includes taxes & fees

2 Nov - 3 Nov

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

12. Home in Great Barrington

Great Barrington

Janet G.

AED 1,314 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.

AED 2,058 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.

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

Great Barrington

Mark M.

AED 2,581 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

AED 12,874 total

includes taxes & fees

18 Oct - 19 Oct

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Top Winsted Hotel Reviews

Quality Inn Great Barrington

8/10 Good

"The hotel is in a good location. There are some good restaurants within walking distance. Only one complaint is that the bathroom fan is very loud."

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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Treat yourself

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Check prices for these dates

Our top choices for Winsted vacation homes

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