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Oct 23 - Oct 24
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Oct 24 - Oct 25
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Oct 23 - Oct 25
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Oct 30 - Nov 1

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Our top choices for Winchester hotels

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
A grand hallway with a chandelier, a staircase, and a table with flowers.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
A room with a fireplace, two striped armchairs, and a floral drape.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Melanie
NT$6,161
NT$7,085 total
includes taxes & fees
Oct 26 - Oct 27
Blackberry River Inn
A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.
A breakfast bar with a coffee machine, toaster, and various food items.
A Days Inn building with a blue awning, a lobby entrance, and a well-maintained lawn with various plants.
A Days Inn sign with a sunburst design, surrounded by trees.

2. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
Torrington
United States
Tyler
NT$2,684
NT$3,086 total
includes taxes & fees
Nov 12 - Nov 13
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.
A spacious living area with a brown leather sofa, a glass coffee table, a wooden entertainment unit with a flat-screen TV, and a large window providing a view of the outdoors.
A motel with a covered entrance, a parking lot, and a building with a sign that reads "LARRY'S".
A gym with various exercise equipment, a mirror, and a blue wall.

3. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
Torrington
United States
Tuty
NT$4,864
NT$5,593 total
includes taxes & fees
Oct 24 - Oct 25
Americas Best Value Inn Torrington CT
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.
A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.
A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.

4. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
United States
Laura
NT$4,399
NT$5,059 total
includes taxes & fees
Nov 19 - Nov 20
Residence Inn by Marriott Hartford Avon
A lobby with a chandelier, a reception desk, and a sign indicating an exit.
A long wooden table with potted plants and candle holders in a modern interior setting.
A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.
A spacious living room with a fireplace, a dining area, and a sofa.

5. The Litchfield Inn

The Litchfield Inn
Litchfield
United States
Jacqueline
NT$9,396
NT$10,805 total
includes taxes & fees
Nov 15 - Nov 16
The Litchfield Inn
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.

6. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
United States
Jessica
NT$4,676
NT$5,377 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn & Suites Hartford/Farmington
A hotel with multiple buildings, a parking lot, and a well-maintained lawn.
A modern lobby with a yellow sofa, marble table, and two armchairs.
A modern kitchen with a central island, built-in cabinets, and a coffee station.
A swimming pool with lounge chairs and a red door.

7. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
United States
EDWARD
NT$4,952
NT$5,695 total
includes taxes & fees
Oct 30 - Oct 31
Homewood Suites by Hilton Hartford-Farmington
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.
A two-story building with a flat roof, solar panels, and a small patio area.
A covered porch with white railings and rocking chairs.
A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

8. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Daniel
NT$3,405
NT$3,916 total
includes taxes & fees
Oct 26 - Oct 27
Locust Tree Bed and Breakfast LLC
A modern hotel lobby with seating arrangements, a central dining table, and a kitchenette area.
A hotel room with a large window, a sofa, a chair, a small table, a TV, and a chessboard.
A reception desk with a wooden backdrop and a large, detailed drawing of a ship.
A hotel room with two beds, a desk, a chair, a TV, a lamp, a small table with bottles, and a framed picture on the wall.

9. Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
Windsor Locks
United States
John
NT$7,442
NT$8,559 total
includes taxes & fees
Nov 21 - Nov 22
Sheraton Hartford Hotel at Bradley Airport
A bedroom with a large bed, a chair, and a window with curtains.
A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.
A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.
A covered porch with a dining area, a sofa, and decorative wall art.

10. The White Hart

The White Hart
Salisbury
United States
William
NT$9,706
NT$11,162 total
includes taxes & fees
Nov 22 - Nov 23
The White Hart
A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.
A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.
A brick building with a covered patio, a fountain, and a staircase leading to a second floor.

11. Simsbury Inn

Simsbury Inn
Simsbury Center
Canada
SueEllen and Ian
NT$9,037
NT$11,101 total
includes taxes & fees
Nov 4 - Nov 5
Simsbury Inn
A large, historic building with a covered porch and outdoor seating area.
A sign for the Simsbury House, indicating it is a historic building from 1820.
A large, historic house with multiple chimneys, a covered porch, and lush greenery.
A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.

12. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
United States
Kimberly
NT$5,896
NT$7,340 total
includes taxes & fees
Nov 4 - Nov 5
Simsbury 1820 House
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A spacious lobby with large windows, a central plant, and multiple hanging lights.

13. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
United States
Jennifer
NT$4,680
NT$5,382 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Hotel Bristol, Connecticut
A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.
A spacious lobby with a grand staircase, multiple seating areas, and a central decorative table.
A large conference room with multiple round tables, beige chairs, chandeliers, and a wooden floor.
A spacious indoor dining area with high ceilings, large windows, and a brick wall.

14. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
United States
Kristen
NT$5,550
NT$7,094 total
includes taxes & fees
Nov 6 - Nov 7
Avon Old Farms Hotel
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.
A large indoor swimming pool with multiple seating areas and large windows.
A modern breakfast area with a counter, seating, and a refrigerator.
A modern lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.

15. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
Bristol
United States
Gabriela
NT$4,228
NT$4,862 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Bristol
A bathroom with a sink, mirror, and towel rack.
A wooden deck with a swing chair and a bench overlooking a lake.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.
A modern hotel room with a bed, sofa, leather chair, and a small table.

16. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
United States
mary
NT$8,726
NT$10,035 total
includes taxes & fees
Nov 8 - Nov 9
Interlaken Inn & Resort
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A white two-story house with a front door, windows, and a chimney.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

17. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
John
NT$9,404
NT$11,348 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.
A well-lit room with a fireplace, two armchairs, a sofa, and a coffee table.
A well-lit living room with a patterned sofa, armchairs, a television, and a patterned carpet.
A four-poster bed in a hotel room with a blue carpet, a desk with a lamp, a chair, and a bedside table with a lamp.

18. The Farmington Inn & Suites

The Farmington Inn & Suites
Farmington
United States
Brian
NT$4,524
NT$5,764 total
includes taxes & fees
Nov 8 - Nov 9
The Farmington Inn & Suites
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
A dining area with a round table, chairs, a fireplace, and a variety of plants.
A modern house with a white exterior, two wooden doors, and a grey awning.
A spacious living room with a large sectional sofa, a round coffee table, and a chandelier. There are large windows with curtains, a fireplace, and a view of greenery outside.

19. Belden House & Mews

Belden House & Mews
Litchfield Historic District
United States
Anthony
NT$14,810
NT$18,333 total
includes taxes & fees
Nov 17 - Nov 18
Belden House & Mews
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.
A modern living room with a sofa, ottoman, and green armchair, a coffee table with a vase of flowers, and a wooden cabinet with decorative items.
A spacious room with a high ceiling, a ceiling fan, a large window with a view of greenery, a white sofa, a black leather chair, and a wooden table with a computer setup.
A house with a garden featuring purple flowers and a stone wall.

20. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
United States
Dean
NT$4,232
NT$6,731 total
includes taxes & fees
Nov 3 - Nov 4
Sunny Peace Homestay
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Stay near popular Winchester attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
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Northwestern Connecticut Community College

Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester.
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Northwestern Connecticut Community College Library

After visiting Northwestern Connecticut Community College Library, make a plan to see the other sights and activities in Winchester.
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Winchester Historical Society

8.0/10 (1 review)
You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area.
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The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.
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Rowley Fields

Explore the great outdoors at Rowley Fields, a lovely green space in Winchester.
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Ledgebrook Plaza

You can enjoy retail therapy at Ledgebrook Plaza during your stay in Winchester.
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American Mural Project

You can spend time studying the exhibits at American Mural Project in Winchester.
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Top Winchester Hotel Reviews

The Abner Hotel

The Abner Hotel

10/10 Excellent
"What a charming in place! My daughter and I stayed there for a couple of nights during our Gilmore Girls weekend and it was a great spot to use as a home base for exploring the area and surrounding towns."
Sheryl 2-night trip
Posted 4 hours ago
The Abner Hotel
Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"great staff with customer service focus!"
Christopher 1-night trip
Posted 13 hours ago
Delamar West Hartford
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Hotel was clean and modern. Hotel bar was fun and front desk was quick, friendly and efficient."
Jennifer 1-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Our room was very clean. They had an excellent breakfast with much to choose from."
Josephine 1-night trip
Posted 4 days ago
The Litchfield Inn
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

10/10 Excellent
"N"
Milo 2-night trip
Posted 4 days ago
Home2 Suites by Hilton Bristol
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent
"Very nice, comfortable stay. Would stay there again."
Erin 1-night trip
Posted 8 days ago
Fairfield Inn & Suites by Marriott Plainville
Simsbury Inn

Simsbury Inn

8/10 Good
"The rooms are nice and very comfortable. The ground are beautiful. The breakfast buffet was often cold and the food not great."
Cynthia 4-night trip
Posted 12 days ago
Simsbury Inn
Troutbeck

Troutbeck

10/10 Excellent
"Absolutely stunning escape. Just go"
Ryan 1-night trip
Posted 1 month ago
Troutbeck

More cheap stays in Winchester

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
NT$2,684
NT$3,086 total
Nov 12 - Nov 13
includes taxes & fees
Days Inn by Wyndham Torrington
PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
NT$2,886
NT$3,319 total
Oct 27 - Oct 28
includes taxes & fees
7.8/10 Good! (221 reviews)
PLYMOUTH MOTOR LODGE
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
NT$3,556
NT$4,089 total
Nov 15 - Nov 16
includes taxes & fees
Extended Stay America Suites Hartford Farmington
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT
NT$4,676
NT$5,377 total
Oct 30 - Oct 31
includes taxes & fees
Hampton Inn & Suites Hartford/Farmington
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT
NT$4,864
NT$5,593 total
Oct 24 - Oct 25
includes taxes & fees
Americas Best Value Inn Torrington CT
The Millerton Inn

The Millerton Inn

53 Main St Millerton NY
NT$8,142
NT$9,211 total
Oct 25 - Oct 26
includes taxes & fees
8.4/10 Very Good! (49 reviews)
The Millerton Inn

Hotels in Winchester with star-rating

Frequently asked questions

What's the best place for a stay in Winchester?
The Farmington Inn & Suites, located 20.6 mi (33.1 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Delamar West Hartford and Extended Stay America Suites Hartford Farmington. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! You'll find that most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.
What are some hotels with pools in Winchester?
Homewood Suites by Hilton Hartford-Farmington: Offers a snack bar/deli, an indoor pool, and buffet. Mayflower Inn & Spa, Auberge Collection and Avon Old Farms Hotel are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester are sure to find plenty to explore and enjoy. In Winchester, there are 21 hotels and other accommodations to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Favorite places to visit include Highland Lake, The Marina at Highland Lake, and Burr Pond State Park. A couple of additional sights to add to your agenda are Winchester Historical Society and American Museum of Tort Law. Check out what more to see and do in Expedia's Winchester guide.
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.

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