Search Resort Hotels in Winsted from CA $105

  • 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

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Winsted

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

1. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (55 reviews)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is CA $165
CA $306 total
includes taxes & fees
Dec 6 - Dec 7
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A wooden cabin interior with a bench, a rug, and a hanging plant.

2. 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 $266 total
includes taxes & fees
Nov 15 - Nov 16
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.

3. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,000 reviews)
"Rooms were very clean, staff was very nice"
United States
Bethany
The price is CA $139
CA $160 total
includes taxes & fees
Nov 10 - Nov 11
Days Inn by Wyndham Torrington
A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.

4. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (837 reviews)
"Clean and the staffs are friendly"
United States
Tuty
The price is CA $210
CA $241 total
includes taxes & fees
Nov 7 - Nov 8
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, (454 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is CA $147
CA $169 total
includes taxes & fees
Nov 9 - Nov 10
Locust Tree Bed and Breakfast LLC
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

6. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (251 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is CA $247
CA $284 total
includes taxes & fees
Nov 8 - Nov 9
Blackberry River Inn
A modern hotel room with a dining area, seating arrangements, and a large TV screen.

7. Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport
2.5 star property
Windsor
9.0 out of 10, Wonderful, (1,005 reviews)
"Close to airport"
United States
Mark
The price is CA $160
CA $184 total
includes taxes & fees
Nov 28 - Nov 29
Hampton Inn Hartford/Airport
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, (854 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 $116
CA $130 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern hotel with a flat roof, large windows, and a covered entrance.

9. Springhill Suites Marriott Airport

Springhill Suites Marriott Airport
3.0 star property
Windsor Locks
8.8 out of 10, Excellent, (1,000 reviews)
"The hotels staff, amenities & atmosphere was great ."
United States
Carolee
The price is CA $146
CA $168 total
includes taxes & fees
Nov 25 - Nov 26
Springhill Suites Marriott Airport
A house with a porch, American flags, and a pathway leading to a bench.

10. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (122 reviews)
"We had a very nice peaceful stay :)"
United States
Melanie
The price is CA $196
CA $217 total
includes taxes & fees
Nov 14 - Nov 15
Truman Gillet House Bed & Breakfast
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

11. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (467 reviews)
"The room was a great size and very clean."
United States
Loren
The price is CA $178
CA $204 total
includes taxes & fees
Nov 22 - Nov 23
Residence Inn by Marriott Hartford Avon
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

12. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is CA $106
CA $118 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Great Barrington
A large, historic building with a covered porch and outdoor seating area.

13. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,002 reviews)
"Restaurant inside inn was comforting and had a great vibe."
United States
Enrique
The price is CA $250
CA $312 total
includes taxes & fees
Nov 9 - Nov 10
Simsbury 1820 House
A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.

14. The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
9.0 out of 10, Wonderful, (1,003 reviews)
"A beautiful inn in a beautiful town. Loved our stay and will definitely be back."
United States
Kenneth
The price is CA $175
CA $225 total
includes taxes & fees
Nov 9 - Nov 10
The Farmington Inn & Suites
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

15. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.0 out of 10, Wonderful, (19 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 $182
CA $290 total
includes taxes & fees
Nov 9 - Nov 10
Sunny Peace Homestay
A two-story house with a front porch, a small balcony, and a white picket fence.

16. 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 $147
CA $499 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Attic 10 min to Llitchfield
A spacious lobby with a grand staircase, multiple seating areas, and a reception desk.

17. Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1,001 reviews)
"We stay every Fall when visiting family. It never disappoints"
United States
Kristen
The price is CA $238
CA $304 total
includes taxes & fees
Nov 7 - Nov 8
Avon Old Farms Hotel
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a landscaped driveway.

18. 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, (1,092 reviews)
"Very good place to stay"
United States
MARITZA RODRIGUEZ
The price is CA $144
CA $166 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Bradley Airport by IHG
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

19. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,001 reviews)
"Very pleased with the hotel & staff. Definitely would stay there again."
United States
Penny
The price is CA $183
CA $210 total
includes taxes & fees
Dec 3 - Dec 4
Hampton Inn & Suites Hartford/Farmington
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

20. 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 $189
CA $333 total
includes taxes & fees
Nov 9 - Nov 10
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
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

Learn more about Winsted

Highland Lake offers refreshing swimming and boating during summer months, with a small beach perfect for families. Explore the American Museum of Tort Law founded by Ralph Nader, then grab coffee at one of Main Street's welcoming cafes.

See all hotels in Winsted
A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.

Top reviews in Winsted

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
Norfolk

10/10 Excellent

Very nice place , staff was very nice also.
Canada
Mark
Reviewed July 21, 2026
Blackberry River Inn

Frequently Asked Questions

What is Winsted like for a resort vacation?

Longing for a relaxing getaway? You deserve all the comforts of a resort, where you can find everything you want for your vacation from tasty food and drink options to activities and shopping. Browse the resort options in the area and discover the best one for you, whether you envision yourself kicking back in a suite with stunning views or hitting the golf course for an afternoon game.

What's a favorite resort in Winsted?

Our top-rated resort near Winsted: Cozy 1-bedroom apartment Farmington Connecticut - 17.4 mi (28 km) from Winsted.

What can I do in Winsted?

Discover the shopping possibilities at Ledgebrook Plaza, or bring the kids to Action Wildlife Foundation for some family fun. For more to see in the area, you can spend time at Highland Lake or Burr Pond State Park.

What's the weather like in Winsted?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winsted are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

What's the best way to get to and around Winsted?

Fly into Bradley Intl. Airport (BDL), which is located 19.3 mi (31 km) away from the city center. You can also search for flights into Westfield, MA (BAF-Barnes Municipal), which is 24.5 mi (39.4 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia