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
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Winsted holiday homes

Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (112 reviews)
"Very nice and comfortable place to stay. I’d definitely return. Breakfast was great."
United States
Lawrence
The price is HK$1,097
HK$1,218 total
includes taxes & fees
20 Jul - 21 Jul
Truman Gillet House Bed & Breakfast
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (430 reviews)
"Below average B&B"
United States
Larry
The price is HK$823
HK$946 total
includes taxes & fees
15 Jul - 16 Jul
Locust Tree Bed and Breakfast LLC
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (580 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is HK$878
HK$980 total
includes taxes & fees
19 Jul - 20 Jul
The Little Lion
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is HK$1,360
HK$1,519 total
includes taxes & fees
19 Jul - 20 Jul
Wilder House Berkshires
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (239 reviews)
"Overall good stay"
United States
Susan
The price is HK$1,279
HK$1,470 total
includes taxes & fees
26 Jul - 27 Jul
Home2 Suites by Hilton Bristol
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (191 reviews)
"beautiful inn"
United States
Maura
The price is HK$1,220
HK$1,403 total
includes taxes & fees
14 Jul - 15 Jul
Blackberry River Inn
Iron/ironing board, free WiFi, bed sheets

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (198 reviews)
"Everything was nice! I'd stay here again!"
United States
SEMORA
The price is HK$697
HK$802 total
includes taxes & fees
12 Jul - 13 Jul
PLYMOUTH MOTOR LODGE
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (877 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is HK$871
HK$973 total
includes taxes & fees
14 Jul - 15 Jul
Monument Mountain Motel
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,014 reviews)
"Great staff. Clean comfortable rooms. Good pillows and mattress and cold A/C"
United States
sarah
The price is HK$926
HK$1,034 total
includes taxes & fees
9 Aug - 10 Aug
Quality Inn Great Barrington
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (94 reviews)
"A little dated but clean. A room for the night for when I race at lime rock"
United States
William
The price is HK$1,019
HK$1,171 total
includes taxes & fees
13 Jul - 14 Jul
Hitching Post Country Motel
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.2 out of 10, Wonderful, (5 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is HK$1,481
HK$1,654 total
includes taxes & fees
10 Aug - 11 Aug
Berkshire Lake Lodge
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (785 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is HK$1,185
HK$1,323 total
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.6 out of 10, Exceptional, (74 reviews)
"I actual live in town and always wanted to stay here with my wife and dine here. Super clean room, very chill atmosphere, well decorated and most importantly, a comfortable bed. The staff was incredible and very attentive. But the real shinning star was the Courthouse restaurant, probably one of the best meals I’m going to have this year. Great vibes, great staff and amazing food. 5/5 stars, would highly recommend staying."
United States
Mark
The price is HK$1,838
HK$2,114 total
includes taxes & fees
23 Jul - 24 Jul
The Abner Hotel
Desk, free cots/infant beds, rollaway beds, free WiFi

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,005 reviews)
"Good clean place to stay "
United States
keith
The price is HK$793
HK$911 total
includes taxes & fees
12 Jul - 13 Jul
Days Inn by Wyndham Torrington
Exterior

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG
2.5 star property
Windsor Locks
8.8 out of 10, Excellent, (1,146 reviews)
"Very comfortable room and staff was courteous. The breakfast area and food was Great."
United States
Loreen
The price is HK$791
HK$910 total
includes taxes & fees
9 Aug - 10 Aug
Holiday Inn Express & Suites Bradley Airport by IHG
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (958 reviews)
"The coffee was fantastic. Rooms were quiet"
United States
Richard
The price is HK$793
HK$885 total
includes taxes & fees
9 Aug - 10 Aug
Quality Inn Westfield - Springfield
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (592 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is HK$776
HK$866 total
includes taxes & fees
20 Jul - 21 Jul
Travelodge by Wyndham Great Barrington Berkshires
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (881 reviews)
"Nice hotel for an overnight trip. Staff was very friendly and helpful."
United States
Brian
The price is HK$1,022
HK$1,141 total
includes taxes & fees
2 Aug - 3 Aug
Hampton Inn Westfield
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
"Staff was very friendly accommodating and helpful"
United States
alecia
The price is HK$1,011
HK$1,298 total
includes taxes & fees
12 Jul - 13 Jul
The Farmington Inn & Suites
Garden

Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (8 reviews)
"Angela is very respectful and generous to her guests."
United States
Jean
The price is HK$966
HK$1,562 total
includes taxes & fees
26 Jul - 27 Jul
Sunny Peace Homestay
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
"Excellent staff. Clean. Beds and towels excellent."
Daniel 1-night trip
Posted 5 hours ago
Quality Inn Great Barrington

Find out more about Winsted

Winsted Vacation Homes information

Number of reviews
10,248
Accommodation
304 Vacation Homes
Lowest Price
HK$802
Highest Price
HK$2,114

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