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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Winsted holiday homes

Interior

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is £265
includes taxes & fees
10 Jun - 11 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor dining

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is £216
includes taxes & fees
7 Jun - 8 Jun
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is £290
includes taxes & fees
8 Jun - 9 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is £259
includes taxes & fees
14 Jun - 15 Jun
Home in Great Barrington
Outdoor dining

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, (65 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is £365
includes taxes & fees
3 Jun - 4 Jun
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is £273
includes taxes & fees
4 Jun - 5 Jun
Big farmhouse in the foothills of the Berkshires
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is £427
includes taxes & fees
3 Jun - 4 Jun
Treetop Hideaway in Tyringham
Terrace/patio

The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
The price is £340
includes taxes & fees
3 Jun - 4 Jun
The Old Avon 1800 Manor
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is £299
includes taxes & fees
9 Jun - 10 Jun
Litchfield Retreat, Wineries, Foliage & Skiing
Property grounds

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 £366
includes taxes & fees
9 Jun - 10 Jun
Cheerful 3-bedroom cottage with woodstove
Property grounds

Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.0 out of 10, (3 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 £226
includes taxes & fees
24 Jun - 25 Jun
Sun Filled Lake House Living
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"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 £387
includes taxes & fees
10 Jun - 11 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Bloomfield
The price is £901
includes taxes & fees
4 Jun - 5 Jun
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Interior

#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 £421
includes taxes & fees
4 Jun - 5 Jun
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is £665
includes taxes & fees
3 Jun - 4 Jun
Whispering Estate Guest House - A Romantic Countryside Getaway
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Great location right outside the airport. Food reasonably priced and delicious."
Stacy 2-night trip
Posted 3 hours ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
8,019
Accommodation
288 Holiday Homes
Lowest Price
£64
Highest Price
£191