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Search Resort Hotels in Winchester from CA $163

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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 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 $142
CA $163 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 $255
CA $293 total
includes taxes & fees
Nov 10 - Nov 11
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 20 - Nov 21
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 $171 total
includes taxes & fees
Nov 10 - Nov 11
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 10 - Nov 11
Cozy Attic 10 min to Llitchfield
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

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 $214
CA $594 total
includes taxes & fees
Nov 10 - Nov 11
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 10 - Nov 11
Cozy Modern Farmhouse Private Apt - 3 Beds
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

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 $399 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 $171
CA $278 total
includes taxes & fees
Nov 10 - Nov 11
Sunny Peace Homestay
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

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 $808 total
includes taxes & fees
Nov 10 - Nov 11
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
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 spacious foyer with a wooden staircase, a reception desk, and a seating area.

14. 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 30 - Dec 1
The Abner Hotel
A modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.

15. 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 $153
CA $192 total
includes taxes & fees
Nov 11 - Nov 12
Collinsville River Escape / Fall Foliage, Deck & Yard
A lobby with a chandelier, a reception desk, and a sign indicating an exit.

16. 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 $450 total
includes taxes & fees
Nov 15 - Nov 16
The Litchfield Inn
A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.

17. The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,008 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 15 - Nov 16
The Farmington Inn & Suites
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

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
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.

19. 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 spacious lobby with a grand staircase, multiple seating areas, and a reception desk.

20. Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1,004 reviews)
"Very cozy and clean. Would absolutely book again"
United States
Alicia
The price is CA $240
CA $307 total
includes taxes & fees
Nov 10 - Nov 11
Avon Old Farms Hotel
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.
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Top Winchester Hotel Reviews

Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"Clean, nice property. Highly recommend."
Katelyn 1-night trip
Posted 1 hour ago
Delamar West Hartford

Find out more about Winchester

Winchester Resorts information

Number of reviews
2,761
Accommodation
1 Resorts
Lowest Price
CA $163
Highest Price
CA $808

Frequently asked questions

What is Winchester like for a resort vacation?
Longing for a relaxing escape? Indulge in all the comforts of a resort, where you can find everything you want for your trip from convenient dining options to activities and shopping. Browse the resorts in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or checking out the on-site boutiques.
What's a top resort for my stay in Winchester?
Our top-rated resort near Winchester: Cozy 1-bedroom apartment Farmington Connecticut - 19.7 mi (31.7 km) from Winchester.
What can I do in Winchester?
Discover the shopping possibilities at Ledgebrook Plaza, or bring the kids to Action Wildlife Foundation for some family fun. Additional attractions in the area include Highland Lake and The Marina at Highland Lake.
What's the seasonal weather like in Winchester?
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 Winchester 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 Winchester?
Fly into Bradley Intl. Airport (BDL), which is located 21.9 mi (35.2 km) away from the heart of the city. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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