Winsted Holiday Homes from £170: 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

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

Winchester

includes taxes & fees

13 Sept - 14 Sept

2. Sun Filled Lake House Living

Avon

Joseph C.

includes taxes & fees

9 Sept - 10 Sept

3. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville

Mike

includes taxes & fees

10 Sept - 11 Sept

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

West Suffield

Wendy C.

includes taxes & fees

13 Sept - 14 Sept

5. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

includes taxes & fees

7 Sept - 8 Sept

6. The Old Avon 1800 Manor

Avon

Anonymous traveller

includes taxes & fees

7 Sept - 8 Sept

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

Sherwood Forest

William C B.

includes taxes & fees

13 Sept - 14 Sept

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

Sherwood Forest

Frank M.

includes taxes & fees

8 Sept - 9 Sept

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

Sherwood Forest

Sharon K.

includes taxes & fees

9 Sept - 10 Sept

10. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

22 Sept - 23 Sept

11. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

8 Sept - 9 Sept

12. 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

21 Sept - 22 Sept

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

Plymouth

includes taxes & fees

1 Oct - 2 Oct

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

Great Barrington

Mary R.

includes taxes & fees

14 Sept - 15 Sept

15. Las Flores Villa

New Preston

includes taxes & fees

1 Oct - 2 Oct

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Top Winsted Hotel Reviews

DoubleTree by Hilton Hartford - Bradley Airport

10/10 Excellent

"The room was clean, the staff were professional and friendly. The breakfast was delicious."

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews	327
Accommodation	283 Holiday Homes
Lowest Price	£170
Highest Price	£2,592

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winsted holiday homes

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

2. Sun Filled Lake House Living

3. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

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

5. Big farmhouse in the foothills of the Berkshires

6. The Old Avon 1800 Manor

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

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

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

10. Cheerful 3-bedroom cottage with woodstove

11. Home in Great Barrington

12. Treetop Hideaway in Tyringham

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

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

15. Las Flores Villa

Find holiday rentals that suit your style

Top Winsted Hotel Reviews

DoubleTree by Hilton Hartford - Bradley Airport

The Farmington Inn & Suites

Avon Old Farms Hotel

Quality Inn Great Barrington

DoubleTree by Hilton Hotel Bristol, Connecticut

Fairfield Inn & Suites by Marriott Plainville

Simsbury 1820 House

Homewood Suites by Hilton Hartford-Farmington

Find out more about Winsted

Winsted Holiday Homes information

Explore a world of travel with Expedia