Search Cottages 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
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
No exact matches found, but these alternatives could be just right

Recommended hotels in Winsted

Exterior

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,004 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is HK$737
HK$823 total
includes taxes & fees
3 Jun - 4 Jun
Quality Inn Great Barrington
Exterior

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (857 reviews)
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
United States
Mark
The price is HK$603
HK$674 total
includes taxes & fees
7 Jun - 8 Jun
Monument Mountain Motel
Exterior

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
The price is HK$1,029
HK$1,149 total
includes taxes & fees
1 Jun - 2 Jun
Berkshire Lake Lodge
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (109 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
1 Jun - 2 Jun
Truman Gillet House Bed & Breakfast
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Great Place!!!"
United States
page
The price is HK$823
HK$946 total
includes taxes & fees
3 Jun - 4 Jun
Locust Tree Bed and Breakfast LLC
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (224 reviews)
"Great place for a quick family getaway!!"
United States
Rosemary
The price is HK$1,442
HK$1,658 total
includes taxes & fees
1 Jun - 2 Jun
Home2 Suites by Hilton Bristol
Exterior

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,003 reviews)
"Rooms were fresh and clean, staff is very friendly and accommodating!"
United States
Amanda
The price is HK$806
HK$927 total
includes taxes & fees
30 Jun - 1 Jul
Days Inn by Wyndham Torrington
Premium bedding, desk, laptop workspace, blackout curtains

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (861 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
The price is HK$993
HK$1,109 total
includes taxes & fees
28 Jun - 29 Jun
Hampton Inn Westfield
Exterior

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (580 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$619
HK$692 total
includes taxes & fees
1 Jun - 2 Jun
Travelodge by Wyndham Great Barrington Berkshires
Exterior

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (933 reviews)
"Very clean& maintained. Most comfortable bed I've slept in"
United States
Keith
The price is HK$808
HK$902 total
includes taxes & fees
1 Jul - 2 Jul
Quality Inn Westfield - Springfield
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, (766 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
The price is HK$1,050
HK$1,173 total
includes taxes & fees
3 Jun - 4 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Terrace/patio

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (65 reviews)
"This is my litchfield go to spot. The location is spectacular the staff is so friendly and professional the rooms are comfortable and well appointed. Breakfast is not to be missed and the restaurant is comfortable savvy . The rooftop is amazing (when open). "
United States
laura
The price is HK$3,095
HK$3,560 total
includes taxes & fees
1 Jun - 2 Jun
The Abner Hotel
Front of property

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is HK$776
HK$867 total
includes taxes & fees
2 Jun - 3 Jun
The Little Lion
Exterior

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (50 reviews)
"My favorite place to stay! Always comfortable and breakfast was great."
United States
Allison
The price is HK$1,511
HK$1,687 total
includes taxes & fees
1 Jun - 2 Jun
Wilder House Berkshires
Front of property

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (184 reviews)
"beautiful inn"
United States
Maura
The price is HK$1,220
HK$1,403 total
includes taxes & fees
2 Jun - 3 Jun
Blackberry River Inn
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Best that can be said is that it was clean. The shower was ok. No on-site staff, we had to check in using a Ring doorbell and bad phone connection. The baseboard heat control required me to get on the floor and crawl into the corner of the room behind the fridge. And the room didn’t look at all like the picture on Expedia. Stay here if you have no other choice."
United States
Andrew
The price is HK$744
HK$1,094 total
includes taxes & fees
1 Jun - 2 Jun
Becket Motel
Exterior

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (782 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is HK$1,525
HK$1,704 total
includes taxes & fees
8 Jun - 9 Jun
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (47 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is HK$1,110
HK$1,240 total
includes taxes & fees
15 Jun - 16 Jun
East Rock Inn
Front of property

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (87 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$1,172 total
includes taxes & fees
1 Jun - 2 Jun
Hitching Post Country Motel
Front of property – evening/night

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (192 reviews)
"Clean"
United States
Young Hwan
The price is HK$697
HK$802 total
includes taxes & fees
1 Jun - 2 Jun
PLYMOUTH MOTOR LODGE
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

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

6/10 Okay
"I have always enjoyed staying at Hampton and have consistently received great service, which is why this experience was so disappointing. We left our room early in the morning expecting it to be cleaned by the time we returned, but it had not been serviced. When I went to the front desk to inquire, I was told that housekeeping needed to prioritize rooms from guests who had checked out so they could be prepared for incoming guests. While I understand that process, in my experience at other hotels, housekeeping is usually able to service occupied rooms before afternoon check-in times. We left again and returned later, only to find that the room still had not been properly cleaned. Fresh towels had been left, and the beds were made, but the sheets had not been changed nor the floor was vacuum nor wiped. There was also a clump of hair on the floor that had not been picked up which was very disappointing. I do want to recognize one staff member who stood out. She had short curly hair and was incredibly kind and welcoming to everyone. Unfortunately, I did not get her name, but she provided excellent customer service and made a positive impression during our stay. I will continue to choose Hampton because of my past positive experiences, but I hope housekeeping standards improve to match the level of service I have come to expect from the brand."
Sabrina 2-night trip
Posted 5 hours ago
Hampton Inn & Suites Hartford/Farmington

Find out more about Winsted

Winsted Cottages information

Number of reviews
8,784
Accommodation
81 Cottages
Lowest Price
HK$674
Highest Price
HK$3,560

Frequently asked questions

Why book your cottage in Winsted with Expedia?
We think that a holiday should be easy, so if you're seeking cottages in Winsted at a great price, Expedia is here to help. Stick to the budget and pick a thrifty option surrounded by wilderness, or splurge on a 5-star cottage to really spoil your favourite people.
How can I find cheap cottages in Winsted?
With Expedia's helpful filter tool, scoring cheap cottages in Winsted is a breeze. To discover properties that'll make your wallet happy, refine your search results by budget, star rating and amenities.

Explore a world of travel with Expedia