Winsted Vacation Homes

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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$1,654 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

HK$1,570 total

includes taxes & fees

13 Oct - 14 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$2,109 total

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

HK$4,125 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with stainless steel appliances, white cabinets, and a wooden floor.

5. Linny's - Private Dock - Lake Access - Firepit

West Suffield

Patricia S.

HK$3,010 total

includes taxes & fees

1 Nov - 2 Nov

A patio area with wicker furniture and a brick floor.

6. The Old Avon 1800 Manor

Avon

Anonymous traveller

HK$3,620 total

includes taxes & fees

12 Oct - 13 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$2,737 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Sherwood Forest

William C B.

HK$2,621 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.

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

Sherwood Forest

Sharon K.

HK$3,071 total

includes taxes & fees

8 Oct - 9 Oct

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

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

Plymouth

Iva B.

HK$6,744 total

includes taxes & fees

8 Oct - 9 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$2,982 total

includes taxes & fees

13 Oct - 14 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$3,456 total

includes taxes & fees

12 Oct - 13 Oct

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

13. Home in Great Barrington

Great Barrington

HEATHER G.

HK$2,729 total

includes taxes & fees

13 Oct - 14 Oct

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.

HK$4,454 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

Mark M.

HK$5,504 total

includes taxes & fees

19 Oct - 20 Oct

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

16. Las Flores Villa

New Preston

HK$27,504 total

includes taxes & fees

8 Oct - 9 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Winsted Hotel Reviews

Simsbury 1820 House

10/10 Excellent

"Lovely comfortable place!!"

The Farmington Inn & Suites

8/10 Good

"The receptionist at the front desk upon arrival was very friendly and helpful. She explained the location of our room, fitness area, breakfast room etc. Even though the building is obviously older, our room was very clean and comfortable. Also the room cleaning staff was very cheerful!"

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."

Find out more about Winsted