Search Winchester Villa Rentals from CA $141

  • 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

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
villa image
Villas
Villas

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A green wooden fence with a mailbox attached to it.

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 $295 total
includes taxes & fees
Nov 22 - Nov 23
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A single-story house with a gravel driveway, surrounded by greenery and trees.

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 Days Inn building with a blue awning, a lobby entrance, and a well-maintained lawn with various plants.

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 $142
CA $163 total
includes taxes & fees
Nov 15 - Nov 16
Days Inn by Wyndham Torrington
A white two-story house with a covered driveway leading to an entrance.

4. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (255 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is CA $255
CA $293 total
includes taxes & fees
Nov 15 - Nov 16
Blackberry River Inn
Exterior

5. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (840 reviews)
"Clean and the staffs are friendly"
United States
Tuty
The price is CA $212
CA $244 total
includes taxes & fees
Nov 12 - Nov 13
Americas Best Value Inn Torrington CT
A covered porch with white railings and rocking chairs.

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 $170 total
includes taxes & fees
Nov 13 - Nov 14
Locust Tree Bed and Breakfast LLC
A two-story house with a front porch, a small balcony, and a white picket fence.

7. 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 12 - Nov 13
Cozy Attic 10 min to Llitchfield
A two-story house with a balcony on the ground floor and a second-floor balcony.

8. 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 $213
CA $609 total
includes taxes & fees
Nov 12 - Nov 13
Art House 3 Beds Close to Warner Theater
A two-story house with a front porch, a small balcony, and a white picket fence.

9. 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 12 - Nov 13
Cozy Modern Farmhouse Private Apt - 3 Beds
A two-story house with a porch, an American flag, and a wreath.

10. 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 $398 total
includes taxes & fees
Nov 16 - Nov 17
Pristine Cozy Walkable Downtown 2BR Getaway
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

11. 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 $169
CA $276 total
includes taxes & fees
Dec 12 - Dec 13
Sunny Peace Homestay
A two-story building with a balcony on the ground floor and a second-floor balcony.

12. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is CA $338
CA $807 total
includes taxes & fees
Nov 12 - Nov 13
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
An outdoor patio area with wooden flooring, green metal chairs, and tables under umbrellas.

13. The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (131 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 $374
CA $431 total
includes taxes & fees
Dec 3 - Dec 4
The Abner Hotel
An outdoor patio with wicker furniture, a glass-top table, and a barbecue grill.

14. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.6 out of 10, Exceptional, (4 reviews)
"Cute and cozy home away from home! We loved our stay and all the nice features there were!! Everything was neat and clean and host was super amazing and helpful! We definitely will choose this place again if we’re ever in the area."
United States
Leah H.
The price is CA $152
CA $181 total
includes taxes & fees
Nov 16 - Nov 17
Collinsville River Escape / Fall Foliage, Deck & Yard
A building with a covered patio area, a brick chimney, and a garden with various plants and shrubs.

15. The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,002 reviews)
"We really enjoyed our stay. Room was clean and quiet."
United States
Philip
The price is CA $391
CA $449 total
includes taxes & fees
Nov 15 - Nov 16
The Litchfield Inn
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

16. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (468 reviews)
"The room was a great size and very clean."
United States
Loren
The price is CA $180
CA $208 total
includes taxes & fees
Nov 22 - Nov 23
Residence Inn by Marriott Hartford Avon
A house with a porch, American flags, and a pathway leading to a bench.

17. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (123 reviews)
"We had a very nice peaceful stay :)"
United States
Melanie
The price is CA $198
CA $219 total
includes taxes & fees
Nov 14 - Nov 15
Truman Gillet House Bed & Breakfast
An outdoor patio with a long table and chairs, a grill, and potted plants.

18. 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
Dec 6 - Dec 7
Home2 Suites by Hilton Bristol
The Avon Old Farms Hotel entrance with a covered walkway and a brick building in the background.

19. Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1,005 reviews)
"Very cozy and clean. Would absolutely book again"
United States
Alicia
The price is CA $177
CA $234 total
includes taxes & fees
Nov 15 - Nov 16
Avon Old Farms Hotel
A two-story building with a sign for The Farmington Inn.

20. The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
9.0 out of 10, Wonderful, (1,001 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 $227 total
includes taxes & fees
Nov 15 - Nov 16
The Farmington Inn & Suites
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 white two-story house with a covered driveway leading to an entrance.
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