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Search Resort Hotels in Winchester from CA $127

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is CA $172
CA $310 total
includes taxes & fees
Sep 13 - Sep 14
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.

2. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,007 reviews)
"New renovation, new floor, new redesign of the room. Studio room is quiet, not a lot of noise from the street get into the room."
United States
Sophornna
The price is CA $135
CA $156 total
includes taxes & fees
Oct 4 - Oct 5
Days Inn by Wyndham Torrington
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

3. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (216 reviews)
"The Inn is lovely and charming - and the breakfast was especially great."
United States
Rachel
The price is CA $191
CA $220 total
includes taxes & fees
Sep 10 - Sep 11
Blackberry River Inn
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

4. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (443 reviews)
"The whole vibe of the B&B was so simple and perfect. 10/10 will stay again."
United States
Nicholas
The price is CA $145
CA $167 total
includes taxes & fees
Sep 8 - Sep 9
Locust Tree Bed and Breakfast LLC
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, (817 reviews)
"Location for the event I attended was very good. Has possibilities of being a very good place to stay."
United States
Carol
The price is CA $188
CA $216 total
includes taxes & fees
Sep 23 - Sep 24
Americas Best Value Inn Torrington CT
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, (116 reviews)
"Cute place. Antiquey Excellent breakfast!"
United States
Valerie
The price is CA $194
CA $215 total
includes taxes & fees
Sep 8 - Sep 9
Truman Gillet House Bed & Breakfast
A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

7. The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.6 out of 10, Exceptional, (90 reviews)
"The hotel is very charming and cozy, and the town is worth spending a few days there."
United States
Eduardo
The price is CA $280
CA $322 total
includes taxes & fees
Sep 20 - Sep 21
The Abner Hotel
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

8. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (13 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 $179
CA $285 total
includes taxes & fees
Sep 23 - Sep 24
Sunny Peace Homestay
A two-story house with a front porch, a small balcony, and a white picket fence.

9. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 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 $116
CA $467 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Attic 10 min to Llitchfield
A bedroom with two beds, a desk, a chair, a window with curtains, and a door with a glass panel.

10. Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (110 reviews)
"Classic 50's/60's motor lodge format. Clean and comfortable. The free WiFi is good to have because cellular data coverage is very sparse."
United States
Chris
The price is CA $180
CA $207 total
includes taxes & fees
Sep 8 - Sep 9
Hitching Post Country Motel
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, (455 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 $199
CA $229 total
includes taxes & fees
Sep 13 - Sep 14
Residence Inn by Marriott Hartford Avon
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

12. 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 $195
CA $597 total
includes taxes & fees
Sep 15 - Sep 16
Art House 3 Beds Close to Warner Theater
A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

13. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is CA $179
CA $559 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

14. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 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 $210
CA $371 total
includes taxes & fees
Sep 21 - Sep 22
Pristine Cozy Walkable Downtown 2BR Getaway
A hotel room with two beds, a nightstand with a lamp, and a wall-mounted phone.

15. PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (210 reviews)
"Everything was nice! I'd stay here again!"
United States
SEMORA
The price is CA $111
CA $127 total
includes taxes & fees
Sep 28 - Sep 29
PLYMOUTH MOTOR LODGE
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, (1,008 reviews)
"The Farmington Inn is charming, comfortable and quiet, with an excellent location and easy access to all that CT has to offer."
United States
Rachael Gagner
The price is CA $188
CA $240 total
includes taxes & fees
Sep 8 - Sep 9
The Farmington Inn & Suites
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

17. 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, (113 reviews)
"We loved our stay! The cottage was adorable!"
United States
Kristen S.
The price is CA $187
CA $346 total
includes taxes & fees
Sep 9 - Sep 10
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

18. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (62 reviews)
"Perfect little b&b."
United States
Mark
The price is CA $256
CA $286 total
includes taxes & fees
Sep 13 - Sep 14
Wilder House Berkshires
A wooden deck with a swing chair and a bench overlooking a lake.

19. Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (312 reviews)
"Great staff and location!"
United States
Stacie
The price is CA $265
CA $304 total
includes taxes & fees
Sep 22 - Sep 23
Interlaken Inn & Resort
A lobby with a chandelier, a reception desk, and a sign indicating an exit.

20. The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,004 reviews)
"Beautiful place 5 stars"
United States
Sandra
The price is CA $391
CA $450 total
includes taxes & fees
Sep 30 - Oct 1
The Litchfield 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.
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Top Winchester Hotel Reviews

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Great location."
Nancy 3-night trip
Posted 15 hours ago
Hampton Inn & Suites Hartford/Farmington

Find out more about Winchester

Winchester Resorts information

Number of reviews
6,788
Accommodation
1 Resorts
Lowest Price
CA $127
Highest Price
CA $470

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 Burr Pond State Park.
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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