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

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 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 HK$1,083
HK$1,884 total
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 HK$761
HK$2,351 total
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 HK$2,448
HK$4,124 total
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 HK$1,490
HK$3,009 total
includes taxes & fees
14 Oct - 15 Oct
Linny's - Private Dock - Lake Access - Firepit
Interior

5. #33- Newly Constructed - Luxury Collection

#33- Newly Constructed - Luxury Collection
Plymouth
#33- Newly Constructed - Luxury Collection
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 HK$455
HK$2,340 total
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 HK$1,396
HK$3,554 total
includes taxes & fees
28 Sept - 29 Sept
The Old Avon 1800 Manor
Property grounds

8. 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 HK$1,491
HK$2,761 total
includes taxes & fees
22 Sept - 23 Sept
Big farmhouse in the foothills of the Berkshires
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 HK$1,144
HK$2,943 total
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.
The price is HK$1,462
HK$3,455 total
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
Outdoor spa tub

11. 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 HK$1,257
HK$3,077 total
includes taxes & fees
27 Sept - 28 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Coffee/tea maker, fridge, microwave, oven

12. 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 HK$1,737
HK$2,711 total
includes taxes & fees
21 Sept - 22 Sept
Home in Great Barrington
TV

13. 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 HK$2,212
HK$4,527 total
includes taxes & fees
21 Sept - 22 Sept
Treetop Hideaway in Tyringham
3 bedrooms, desk, WiFi, bed sheets

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

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is HK$2,717
HK$6,758 total
includes taxes & fees
15 Oct - 16 Oct
Lakehaven • Hot Tub, Decks, Fires & More
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$3,287
HK$5,696 total
includes taxes & fees
23 Sept - 24 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Exterior

16. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is HK$21,181
HK$27,496 total
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

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Good location. Shuttle offered to wedding. Good venue for after party."
Katherine 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut

Find out more about Winsted

Winsted Vacation Homes information

Number of reviews
219
Accommodation
282 Vacation Homes
Lowest Price
HK$1,884
Highest Price
HK$27,496

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