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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winsted holiday homes

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, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is HK$1,450
HK$2,733 total
includes taxes & fees
26 May - 27 May
Big farmhouse in the foothills of the Berkshires
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 HK$1,255
HK$3,091 total
includes taxes & fees
1 Jun - 2 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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 HK$1,142
HK$2,922 total
includes taxes & fees
26 May - 27 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 HK$2,200
HK$3,806 total
includes taxes & fees
26 May - 27 May
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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 HK$1,587
HK$2,499 total
includes taxes & fees
26 May - 27 May
Home in Great Barrington
Interior

Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events
Bloomfield
10.0 out of 10, Exceptional, (5 reviews)
"House was very spacious."
United States
Christina H.
The price is HK$2,318
HK$5,514 total
includes taxes & fees
1 Jun - 2 Jun
Stylish Townhome | Perfect for Family Gatherings & Events
Exterior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$677
HK$2,603 total
includes taxes & fees
10 Jun - 11 Jun
Real Estate: Therapy - Lake, Laundry, Love it
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is HK$2,045
HK$3,116 total
includes taxes & fees
31 May - 1 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 HK$1,857
HK$3,947 total
includes taxes & fees
1 Jun - 2 Jun
Cheerful 3-bedroom cottage with woodstove
Terrace/patio

The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
The price is HK$1,387
HK$3,540 total
includes taxes & fees
27 May - 28 May
The Old Avon 1800 Manor
Smart TV

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Bloomfield
9.0 out of 10, Wonderful, (6 reviews)
"I had a great time and I felt very welcome"
United States
Avis b.
The price is HK$2,310
HK$5,753 total
includes taxes & fees
2 Jun - 3 Jun
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
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 HK$2,210
HK$4,530 total
includes taxes & fees
1 Jun - 2 Jun
Treetop Hideaway in Tyringham
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 HK$2,758
HK$5,295 total
includes taxes & fees
16 Jun - 17 Jun
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
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 HK$580
HK$2,083 total
includes taxes & fees
28 May - 29 May
Sun Filled Lake House Living
Exterior

Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is HK$7,969
HK$12,298 total
includes taxes & fees
26 May - 27 May
Las Flores Villa
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 HK$2,351
HK$4,175 total
includes taxes & fees
31 May - 1 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior

Group-Friendly Townhouse Stay – Sleeps up to 20

Group-Friendly Townhouse Stay – Sleeps up to 20
Bloomfield
8.0 out of 10, Very good, (3 reviews)
"This was a terrific spot for our weekend plans to fly in and see a UCONN Husky basketball game in Hartford! Hope was comfortable and clean. Will definitely plan to stay here again. "
United States
Paul L.
The price is HK$3,448
HK$9,410 total
includes taxes & fees
27 May - 28 May
Group-Friendly Townhouse Stay – Sleeps up to 20
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 HK$4,231
HK$6,923 total
includes taxes & fees
26 May - 27 May
Whispering Estate Guest House - A Romantic Countryside Getaway
Fridge, microwave, oven, stovetop

Premium 3-Story Townhome | Perfect for Large Groups

Premium 3-Story Townhome | Perfect for Large Groups
Bloomfield
8.4 out of 10, Very good, (7 reviews)
"Great stay. "
United States
Le Dung H.
The price is HK$2,655
HK$5,948 total
includes taxes & fees
1 Jun - 2 Jun
Premium 3-Story Townhome | Perfect for Large Groups
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

The Little Lion

The Little Lion

10/10 Excellent
"Great"
Michael 2-night trip
Posted less than an hour ago
The Little Lion

Find out more about Winsted

Winsted Vacation Homes information

Number of reviews
330
Accommodation
293 Vacation Homes
Lowest Price
HK$2,083
Highest Price
HK$12,298

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