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

Search Chalets in Winsted from CA $119

  • 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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14
No exact matches found, but these alternatives could be just right

Recommended hotels in Winsted

A single-story house with a gravel driveway, surrounded by greenery and trees.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is CA $145
CA $279 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A Days Inn building with a blue awning, a lobby entrance, and a well-maintained lawn with various plants.

2. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,008 reviews)
"It’s a good place to stay for a night, and the staff there are extremely friendly."
United States
Tyler
The price is CA $116
CA $133 total
includes taxes & fees
Nov 11 - Nov 12
Days Inn by Wyndham Torrington
A white two-story house with a covered driveway leading to an entrance.

3. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (242 reviews)
"Quiet room Wonderful breakfast Pleasant atmosphere"
United States
Donna
The price is CA $238
CA $273 total
includes taxes & fees
Nov 2 - Nov 3
Blackberry River Inn
A motel with a covered entrance, a parking lot, and a building with a sign that reads "LARRY'S".

4. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (830 reviews)
"Clean and the staffs are friendly"
United States
Tuty
The price is CA $211
CA $242 total
includes taxes & fees
Oct 24 - Oct 25
Americas Best Value Inn Torrington CT
A covered porch with white railings and rocking chairs.

5. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (452 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is CA $148
CA $170 total
includes taxes & fees
Oct 25 - Oct 26
Locust Tree Bed and Breakfast LLC
A house with a porch, American flags, and a pathway leading to a bench.

6. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (120 reviews)
"We had a very nice peaceful stay :)"
United States
Melanie
The price is CA $197
CA $218 total
includes taxes & fees
Oct 29 - Oct 30
Truman Gillet House Bed & Breakfast
A large, two-story house with a steeply pitched roof, stone foundation, and a well-maintained garden with various shrubs and a fountain.

7. Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (141 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
Manor House Inn
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

8. 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, (841 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is CA $126
CA $141 total
includes taxes & fees
Nov 18 - Nov 19
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

9. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,000 reviews)
"Our stay was great everything was very clean and the breakfast had a great selection"
United States
Jessica
The price is CA $202
CA $232 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn & Suites Hartford/Farmington
An outdoor patio with tables and chairs, a wooden ceiling, and a view of trees and buildings.

10. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,000 reviews)
"Such a warm welcome from the wonderful woman at the desk, beautiful inn with a very comfortable bed and on site restaurant which is super convenient! Loved our stay!"
United States
Kimberly
The price is CA $239
CA $300 total
includes taxes & fees
Nov 4 - Nov 5
Simsbury 1820 House
A house with a garden featuring purple flowers and a stone wall.

11. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
8.8 out of 10, Excellent, (18 reviews)
"When I arrived after dark, it was hard to tell if I was at the right house. The bedroom was clean and quiet. Appears to be a shared bathroom but lucky one of the two bedrooms were vacant. Good for a quick stay."
United States
Dean
The price is CA $183
CA $292 total
includes taxes & fees
Nov 2 - Nov 3
Sunny Peace Homestay
The Avon Old Farms Hotel entrance with a covered walkway and a brick building in the background.

12. Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1,000 reviews)
"We stay every Fall when visiting family. It never disappoints"
United States
Kristen
The price is CA $240
CA $307 total
includes taxes & fees
Nov 6 - Nov 7
Avon Old Farms Hotel
A two-story house with a front porch, a small balcony, and a white picket fence.

13. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is CA $148
CA $524 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Attic 10 min to Llitchfield
A two-story building with a sign for The Farmington Inn.

14. The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
"Clean room friendly staff nice breakfast"
United States
Brian
The price is CA $176
CA $226 total
includes taxes & fees
Nov 9 - Nov 10
The Farmington Inn & Suites
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

15. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (465 reviews)
"It was such a great experience, the hotel was so nice and clean. Plenty of things for the kids to do. And we were able to walk to get ice cream after dinner."
United States
Laura
The price is CA $190
CA $218 total
includes taxes & fees
Nov 19 - Nov 20
Residence Inn by Marriott Hartford Avon
A Quality Inn sign, a brick building, and a parking lot with cars.

16. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"good location, friendly helpful staff"
United States
Scott Patterson
The price is CA $106
CA $119 total
includes taxes & fees
Nov 12 - Nov 13
Quality Inn Great Barrington
An outdoor patio area with wooden flooring, green metal chairs, and tables under umbrellas.

17. The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (116 reviews)
"A really cute place to stay for the night during our travels. Highly recommend the rooftop bar!"
United States
Maria
The price is CA $289
CA $332 total
includes taxes & fees
Nov 11 - Nov 12
The Abner Hotel
A two-story house with a balcony on the ground floor and a second-floor balcony.

18. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is CA $212
CA $633 total
includes taxes & fees
Oct 25 - Oct 26
Art House 3 Beds Close to Warner Theater
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

19. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (117 reviews)
"We loved our stay! The cottage was adorable!"
United States
Kristen S.
The price is CA $190
CA $350 total
includes taxes & fees
Nov 5 - Nov 6
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A brick building with a covered patio, a fountain, and a staircase leading to a second floor.

20. Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (316 reviews)
"Loved the 4 post beds and the linens were the nicest I have ever slept in. Lots of free parking on sight with a couple of outdoor fire pits. I would definitely stay there when we are in Simsbury"
Canada
SueEllen and Ian
The price is CA $391
CA $481 total
includes taxes & fees
Nov 4 - Nov 5
Simsbury Inn
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 Westfield - Springfield

Quality Inn Westfield - Springfield

10/10 Excellent
"Great place for the money. Would stay there again"
Mark 1-night trip
Posted 2 days ago
Quality Inn Westfield - Springfield

Find out more about Winsted

Winsted Chalets information

Number of reviews
3,970
Accommodation
2 Chalets
Lowest Price
CA $119
Highest Price
CA $633

Explore a world of travel with Expedia