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

Holiday Homes in Winsted

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winsted holiday homes

Interior

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (1 review)
"Great place and wonderful host."
United States
Thomas C.
The price is €200
includes taxes & fees
4 Oct - 5 Oct
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Property grounds

2. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is €270
includes taxes & fees
24 Sept - 25 Sept
Sun Filled Lake House Living
Outdoor dining

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

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (72 reviews)
"Wow! What a great place! The house is lovely, very clean, comfy beds and cozy seating. Amazing view and an unbeatable location!"
United States
Kristi M.
The price is €459
includes taxes & fees
28 Sept - 29 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Interior

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

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is €336
includes taxes & fees
14 Oct - 15 Oct
Linny's - Private Dock - Lake Access - Firepit
Property grounds

5. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (151 reviews)
"Great location"
United States
Will G.
The price is €313
includes taxes & fees
22 Sept - 23 Sept
Big farmhouse in the foothills of the Berkshires
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is €258
includes taxes & fees
24 Sept - 25 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Terrace/patio

7. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is €384
includes taxes & fees
28 Sept - 29 Sept
The Old Avon 1800 Manor
Outdoor spa tub

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is €339
includes taxes & fees
27 Sept - 28 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €325
includes taxes & fees
28 Sept - 29 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Property grounds

10. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

11. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is €287
includes taxes & fees
24 Sept - 25 Sept
Home in Great Barrington
TV

12. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"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!! "
United States
Samantha G.
The price is €495
includes taxes & fees
22 Sept - 23 Sept
Treetop Hideaway in Tyringham
Smart TV, books, printers

13. Guest Fave Cape-Cod Style Retreat with Main-Level Bedroom bordering Farmington

Guest Fave Cape-Cod Style Retreat with Main-Level Bedroom bordering Farmington
New Britain
9.6 out of 10, Exceptional, (8 reviews)
"We enjoyed our trip and the house was perfect for us, 3 boys and their father. "
United States
Todd S.
Guest Fave Cape-Cod Style Retreat with Main-Level Bedroom bordering Farmington
3 bedrooms, desk, WiFi, bed sheets

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

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is €751
includes taxes & fees
4 Oct - 5 Oct
Lakehaven • Hot Tub, Decks, Fires & More
Interior

15. #11 - 4 Bedrooms, 3 Baths! Sleeps up to 8

#11 - 4 Bedrooms, 3 Baths! Sleeps up to 8
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
#11 - 4 Bedrooms, 3 Baths! Sleeps up to 8
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is €628
includes taxes & fees
23 Sept - 24 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Exterior

17. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €3,052
includes taxes & fees
1 Oct - 2 Oct
Las Flores Villa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winsted Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Very nice stay. Nice town to stay in."
Wendy L 1-night trip
Posted 9 hours ago
Quality Inn Great Barrington

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
231
Accommodation
288 Holiday Homes
Lowest Price
€200
Highest Price
€3,052