Winsted Holiday Homes from £152: Search Holiday Homes in Winsted

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.

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

Brandon R.

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.

includes taxes & fees

26 Oct - 27 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

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

includes taxes & fees

26 Oct - 27 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.

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.

includes taxes & fees

3 Nov - 4 Nov

A staircase with a wooden handrail and a white wall with a large, oval-shaped mirror.

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

Plymouth

Iva B.

includes taxes & fees

22 Oct - 23 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.

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.

includes taxes & fees

28 Oct - 29 Oct

A spacious living room with a brown leather sofa, a dining area with a wooden table and chairs, and a kitchen with stainless steel appliances.

11. #11 - 4 Bedrooms, 3 Baths! Sleeps up to 8

Plainville

Neil R.

includes taxes & fees

30 Oct - 31 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.

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.

includes taxes & fees

3 Nov - 4 Nov

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

14. 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.

includes taxes & fees

16 Nov - 17 Nov