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Winchester Hotels from S$121

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Check prices for these dates

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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Our top choices for Winchester hotels

A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.
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.
A breakfast bar with a coffee machine, toaster, and various food items.

1. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
Torrington
United States
Tyler
S$121
includes taxes & fees
12 Nov - 13 Nov
Days Inn by Wyndham Torrington
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
A room with a fireplace, two striped armchairs, and a floral drape.
A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

2. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Melanie
S$254
includes taxes & fees
25 Oct - 26 Oct
Blackberry River Inn
A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.
A gym with various exercise equipment, a mirror, and a blue wall.
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".

3. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
Torrington
United States
Tuty
S$220
includes taxes & fees
30 Oct - 31 Oct
Americas Best Value Inn Torrington CT
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.
A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.
A two-story building with a flat roof, solar panels, and a small patio area.
A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

4. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Daniel
S$154
includes taxes & fees
30 Oct - 31 Oct
Locust Tree Bed and Breakfast LLC
A house with a porch, American flags, and a pathway leading to a bench.
A dining room with a table set for four, surrounded by wooden chairs. A chandelier hangs above the table, and a vase with flowers is on the table.
A wooden desk with a notebook, two mugs, a framed sign, a telephone, and a decorative bowl.
A four-poster bed with floral bedding, two bedside lamps, and a wooden floor.

5. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
Granby
United States
Melanie
S$198
includes taxes & fees
28 Oct - 29 Oct
Truman Gillet House Bed & Breakfast
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

6. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
United States
Jessica
S$211
includes taxes & fees
20 Nov - 21 Nov
Hampton Inn & Suites Hartford/Farmington
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.
A modern lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.
A large indoor swimming pool with multiple seating areas and large windows.
A modern breakfast area with a counter, seating, and a refrigerator.

7. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
Bristol
United States
Gabriela
S$192
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Bristol
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 chairs, a coffee table with flowers, and a side table with a lamp and decorative items.
A house with a garden featuring purple flowers and a stone wall.
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.

8. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
United States
Dean
S$265
includes taxes & fees
2 Nov - 3 Nov
Sunny Peace Homestay
A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.
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.
A well-lit room with a fireplace, two armchairs, a sofa, and a coffee table.

9. The Farmington Inn & Suites

The Farmington Inn & Suites
Farmington
United States
Brian
S$210
includes taxes & fees
8 Nov - 9 Nov
The Farmington Inn & Suites
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.
A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

10. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
United States
Laura
S$199
includes taxes & fees
19 Nov - 20 Nov
Residence Inn by Marriott Hartford Avon
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 reception desk.
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.

11. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
United States
Kristen
S$287
includes taxes & fees
1 Nov - 2 Nov
Avon Old Farms Hotel
A large, historic building with a covered porch and outdoor seating area.
A large, historic house with multiple chimneys, a covered porch, and lush greenery.
A sign for the Simsbury House, indicating it is a historic building from 1820.
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
S$289
includes taxes & fees
25 Oct - 26 Oct
Simsbury 1820 House
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
A spacious lobby with large windows, a central plant, and multiple hanging lights.
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.

13. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
United States
Jennifer
S$216
includes taxes & fees
8 Nov - 9 Nov
DoubleTree by Hilton Hotel Bristol, Connecticut
Interior detail
A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.
A bedroom with a large bed, a dresser, a chair, and a mirror.
A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

14. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Liliana
S$234
includes taxes & fees
27 Oct - 28 Oct
Wilder House Berkshires
A lobby with a chandelier, a reception desk, and a sign indicating an exit.
A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.
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.

15. The Litchfield Inn

The Litchfield Inn
Litchfield
United States
Jacqueline
S$424
includes taxes & fees
15 Nov - 16 Nov
The Litchfield Inn
A lobby with a blue sofa, a small round table, and a fireplace.
A hotel room with a sofa, two small tables, a TV, a desk, and a mirror.
A Fairfield Inn & Suites hotel with a large parking lot and snow-covered ground.
An indoor swimming pool with a 'No Diving' sign, a glass enclosure, and a tiled wall with a 'No Diving' sign.

16. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
Plainville
United States
Erin
S$149
includes taxes & fees
8 Nov - 9 Nov
Fairfield Inn & Suites by Marriott Plainville
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
A swimming pool with lounge chairs and umbrellas, surrounded by trees.
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.

17. Belden House & Mews

Belden House & Mews
Litchfield Historic District
United States
Anthony
S$693
includes taxes & fees
18 Nov - 19 Nov
Belden House & Mews
A hotel with multiple buildings, a parking lot, and a well-maintained lawn.
A swimming pool with lounge chairs and a red door.
A modern kitchen with a central island, built-in cabinets, and a coffee station.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a lamp.

18. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
United States
EDWARD
S$242
includes taxes & fees
25 Oct - 26 Oct
Homewood Suites by Hilton Hartford-Farmington
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
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.

19. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
John
S$447
includes taxes & fees
14 Nov - 15 Nov
The Old Inn On The Green
A bedroom with two beds, a desk, a chair, a window with curtains, and a door with a glass panel.
A motel sign with a 'VACANCY' notice, surrounded by well-maintained landscaping and a building with a red roof.
A room with a mounted television, a chair, and a coat rack.
A bathroom with a white sink, a dark wooden vanity, and a drawer with a white towel.

20. Hitching Post Country Motel

Hitching Post Country Motel
Cornwall Bridge
United States
Chris
S$191
includes taxes & fees
30 Oct - 31 Oct
Hitching Post Country Motel
View all properties

Hotels recommended for families in Winchester

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

Blackberry River Inn

Blackberry River Inn
Norfolk
S$254
includes taxes & fees
25 Oct - 26 Oct
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 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.
A breakfast bar with a coffee machine, toaster, and various food items.

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
Torrington
S$121
includes taxes & fees
12 Nov - 13 Nov
Days Inn by Wyndham Torrington
An outdoor patio with a circular fire pit surrounded by wicker chairs, a grill, and a dining area with tables and chairs.
A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
S$199
includes taxes & fees
19 Nov - 20 Nov
Residence Inn by Marriott Hartford Avon
A lobby with a chandelier, a reception desk, and a sign indicating an exit.
A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.
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.

The Litchfield Inn

The Litchfield Inn
Litchfield
S$424
includes taxes & fees
15 Nov - 16 Nov
The Litchfield Inn
A hotel with a prominent sign, a covered entrance, and a landscaped driveway.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.
An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.
A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
S$211
includes taxes & fees
20 Nov - 21 Nov
Hampton Inn & Suites Hartford/Farmington
A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.
A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.
A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.
A person in a blue swimsuit relaxing in a hot tub with a pool in the background.

Simsbury Inn

Simsbury Inn
Simsbury Center
S$437
includes taxes & fees
4 Nov - 5 Nov
Simsbury Inn
A hotel with multiple buildings, a parking lot, and a well-maintained lawn.
A swimming pool with lounge chairs and a red door.
A modern kitchen with a central island, built-in cabinets, and a coffee station.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a lamp.

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
S$242
includes taxes & fees
25 Oct - 26 Oct
Homewood Suites by Hilton Hartford-Farmington
A modern hotel lobby with seating arrangements, a central dining table, and a kitchenette area.
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.
A hotel kitchenette with a microwave, coffee maker, and a sink.

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
Windsor Locks
S$336
includes taxes & fees
21 Nov - 22 Nov
Sheraton Hartford Hotel at Bradley Airport
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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

Explore the campus of Northwestern Connecticut Community College during your stay in 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 studying the exhibits at Winchester Historical Society in 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 do some window-shopping at Ledgebrook Plaza during your visit to Winchester.
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American Mural Project

You can spend time browsing the exhibits at American Mural Project during your trip to Winchester.
See properties

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 1 hour ago
The Abner Hotel
Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"great staff with customer service focus!"
Christopher 1-night trip
Posted 10 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 11 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
S$121
12 Nov - 13 Nov
includes taxes & fees
Days Inn by Wyndham Torrington
PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
S$123
23 Nov - 24 Nov
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
S$160
15 Nov - 16 Nov
includes taxes & fees
Extended Stay America Suites Hartford Farmington
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT
S$211
20 Nov - 21 Nov
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
S$220
30 Oct - 31 Oct
includes taxes & fees
Americas Best Value Inn Torrington CT
The Millerton Inn

The Millerton Inn

53 Main St Millerton NY
S$301
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very good! (49 reviews)
The Millerton Inn

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 traveller data. Two other choices for your stay in 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, most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
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 on-site pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester will definitely find plenty to explore and enjoy. In Winchester, there are 21 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I see while I'm in Winchester?
Favourite 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 itinerary are Winchester Historical Society and American Museum of Tort Law. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the seasonal weather in Winchester?
The hottest months are usually July and August, with an average temperature of 20ยฐC, while the coldest months are January and February, with an average of -1ยฐC. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 15 cm of snowfall.

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