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

Search Vacation Homes in Winsted

  • 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
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winsted vacation homes

2 bedrooms, WiFi (free), bed sheets

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 456
AED 828 total
includes taxes & fees
13 Sep - 14 Sep
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 AED 371
AED 1,133 total
includes taxes & fees
7 Sep - 8 Sep
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, (71 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,146
AED 1,942 total
includes taxes & fees
10 Sep - 11 Sep
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 AED 681
AED 1,396 total
includes taxes & fees
13 Sep - 14 Sep
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, (149 reviews)
"Great location"
United States
Will G.
The price is AED 698
AED 1,308 total
includes taxes & fees
3 Sep - 4 Sep
Big farmhouse in the foothills of the Berkshires
Terrace/patio

6. 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 traveler
The price is AED 738
AED 1,799 total
includes taxes & fees
10 Sep - 11 Sep
The Old Avon 1800 Manor
Interior

7. 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 AED 187
AED 1,063 total
includes taxes & fees
13 Sep - 14 Sep
Real Estate: Therapy - Lake, Laundry, Love it
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 AED 588
AED 1,457 total
includes taxes & fees
7 Sep - 8 Sep
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 AED 536
AED 1,386 total
includes taxes & fees
9 Sep - 10 Sep
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, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 907
AED 1,908 total
includes taxes & fees
22 Sep - 23 Sep
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, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 876
AED 1,352 total
includes taxes & fees
7 Sep - 8 Sep
Home in Great Barrington
Interior

12. #11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
The price is AED 1,175
AED 2,358 total
includes taxes & fees
12 Sep - 13 Sep
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
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 AED 1,036
AED 2,139 total
includes taxes & fees
21 Sep - 22 Sep
Treetop Hideaway in Tyringham
Outdoor dining

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

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is AED 1,272
AED 3,197 total
includes taxes & fees
1 Oct - 2 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 AED 1,165
AED 2,036 total
includes taxes & fees
14 Sep - 15 Sep
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 AED 9,917
AED 12,874 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winsted Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"It is a good value for money. Location is very good, right on the main street, just one block away from downtown Great Barrington with almost all the restaurants and shops within walking distance. Downside is that it is a motel, not a standard hotel. If you have a room on the second floor then you have to haul your luggage up as there is no elevator. Breakfast has bare minimum items. It would help if fresh fruit and cereal is added. There is improvement possible in the overall upkeep. However, I'll certainly recommend it for a short stay for budget customers like me."
SANJAY 2-night trip
Posted 2 hours ago
Quality Inn Great Barrington

Explore a world of travel with Expedia