Search Lodges in Winchester from CA $140

  • 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 Winchester

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 $153
CA $294 total
includes taxes & fees
Nov 22 - Nov 23
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, (5 reviews)
The price is CA $146
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, (1,001 reviews)
"Rooms were very clean, staff was very nice"
United States
Bethany
The price is CA $141
CA $162 total
includes taxes & fees
Nov 12 - Nov 13
Days Inn by Wyndham Torrington
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

4. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (253 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is CA $252
CA $290 total
includes taxes & fees
Nov 12 - Nov 13
Blackberry River Inn
A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.

5. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (839 reviews)
"Clean and the staffs are friendly"
United States
Tuty
The price is CA $206
CA $237 total
includes taxes & fees
Nov 11 - Nov 12
Americas Best Value Inn Torrington CT
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

6. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (455 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is CA $148
CA $171 total
includes taxes & fees
Nov 10 - Nov 11
Locust Tree Bed and Breakfast LLC
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

7. 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 $214
CA $594 total
includes taxes & fees
Nov 9 - Nov 10
Art House 3 Beds Close to Warner Theater
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

8. 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 $180
CA $207 total
includes taxes & fees
Nov 22 - Nov 23
Residence Inn by Marriott Hartford Avon
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

9. 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 $171
CA $278 total
includes taxes & fees
Nov 10 - Nov 11
Sunny Peace Homestay
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

10. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (285 reviews)
"Everything was wonderful , we enjoy a lot the hot tub and the go to pool that feels amazing"
United States
Gabriela
The price is CA $184
CA $212 total
includes taxes & fees
Nov 15 - Nov 16
Home2 Suites by Hilton Bristol
A large, historic building with a covered porch and outdoor seating area.

11. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,003 reviews)
"Restaurant inside inn was comforting and had a great vibe."
United States
Enrique
The price is CA $253
CA $315 total
includes taxes & fees
Nov 9 - Nov 10
Simsbury 1820 House
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

12. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is CA $244
CA $399 total
includes taxes & fees
Nov 17 - Nov 18
Pristine Cozy Walkable Downtown 2BR Getaway
A house with a porch, American flags, and a pathway leading to a bench.

13. 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 $198
CA $220 total
includes taxes & fees
Nov 14 - Nov 15
Truman Gillet House Bed & Breakfast
A two-story house with a front porch, a small balcony, and a white picket fence.

14. 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 $504 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Attic 10 min to Llitchfield
A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

15. The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (128 reviews)
"The Abner Hotel is beautiful, very clean, and has a lovely, welcoming atmosphere. Overall, everything was great, and we had a very pleasant stay."
United States
DIEGO
The price is CA $375
CA $431 total
includes taxes & fees
Nov 29 - Nov 30
The Abner Hotel
A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.

16. The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,007 reviews)
"A beautiful inn in a beautiful town. Loved our stay and will definitely be back."
United States
Kenneth
The price is CA $177
CA $228 total
includes taxes & fees
Nov 9 - Nov 10
The Farmington Inn & Suites
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

17. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,003 reviews)
"Very pleased with the hotel & staff. Definitely would stay there again."
United States
Penny
The price is CA $185
CA $213 total
includes taxes & fees
Dec 3 - Dec 4
Hampton Inn & Suites Hartford/Farmington
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

18. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1,003 reviews)
"Lovely stay, easy check in and kind staff. The room was clean and comfortable"
United States
Julia
The price is CA $197
CA $226 total
includes taxes & fees
Nov 22 - Nov 23
DoubleTree by Hilton Hotel Bristol, Connecticut
A two-story house with a front porch, a small balcony, and a white picket fence.

19. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is CA $199
CA $578 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Modern Farmhouse Private Apt - 3 Beds
A lobby with a blue sofa, a small round table, and a fireplace.

20. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.4 out of 10, Very good, (1,008 reviews)
"Very nice, comfortable stay. Would stay there again."
United States
Erin
The price is CA $148
CA $170 total
includes taxes & fees
Nov 19 - Nov 20
Fairfield Inn & Suites by Marriott Plainville
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

Top reviews in Winchester

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

Explore a world of travel with Expedia