Default HTG hotel image

Winchester Hotels from S$142

  • 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

Check prices for these dates

Tonight
7 Sept - 8 Sept
Tomorrow
8 Sept - 9 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Filter by

Star rating

Guest rating

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 kitchen area with a counter, a microwave, a coffee machine, and a display case with pastries.
A Days Inn sign with a sunburst design, surrounded by trees.

1. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
Torrington
United States
Sophornna
S$142
includes taxes & fees
4 Oct - 5 Oct
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
Rachel
S$205
includes taxes & fees
8 Oct - 9 Oct
Blackberry River Inn
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 covered porch with white railings and rocking chairs.
A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

3. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Nicholas
S$153
includes taxes & fees
8 Sept - 9 Sept
Locust Tree Bed and Breakfast LLC
A patio with a round metal table, a glass of white wine, and a red umbrella.
A dining table with a plate of food and two wine glasses, set in a room with leather furniture and a fireplace in the background.
A large, two-story house with a steeply pitched roof, stone foundation, and a well-maintained garden with various shrubs and a fountain.
A grand staircase with a wooden railing, leading to a room with large windows and a patterned ceiling.

4. Manor House Inn

Manor House Inn
Norfolk
United States
Kevin
S$430
includes taxes & fees
14 Sept - 15 Sept
Manor House Inn
A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.
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.

5. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
Torrington
United States
Carol
S$199
includes taxes & fees
20 Sept - 21 Sept
Americas Best Value Inn Torrington CT
A house with a porch, American flags, and a pathway leading to a bench.
A four-poster bed with floral bedding, two bedside lamps, and a wooden floor.
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 living room with a fireplace, a wooden cabinet, a plaid sofa, and a patterned rug.

6. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
Granby
United States
Valerie
S$197
includes taxes & fees
8 Sept - 9 Sept
Truman Gillet House Bed & Breakfast
A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.
A spacious foyer with a wooden staircase, a reception desk, and a seating area.
An outdoor patio area with wooden flooring, green metal chairs, and tables under umbrellas.
An outdoor seating area with green chairs and tables, a bar with shelves of bottles, and a view of trees in the background.

7. The Abner Hotel

The Abner Hotel
Litchfield Historic District
United States
Eduardo
S$295
includes taxes & fees
20 Sept - 21 Sept
The Abner Hotel
A spacious foyer with a grand staircase, a chandelier, and a patterned carpet.
A spacious lobby with a patterned rug, a potted plant, and a television.
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.

8. The Farmington Inn & Suites

The Farmington Inn & Suites
Farmington
United States
Rachael Gagner
S$222
includes taxes & fees
8 Sept - 9 Sept
The Farmington Inn & Suites
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 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.

9. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
United States
Dean
S$263
includes taxes & fees
8 Sept - 9 Sept
Sunny Peace Homestay
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 hotel building with multiple floors and a prominent "HOME 2 SUITES BY HILTON" sign.
A modern breakfast area with a counter, seating, and a refrigerator.

10. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
Bristol
United States
Laura
S$190
includes taxes & fees
20 Sept - 21 Sept
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.
A Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.
A stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.
A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.

11. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
United States
Laura
S$209
includes taxes & fees
27 Sept - 28 Sept
Residence Inn by Marriott Hartford Avon
A bedroom with a large bed, a dresser, a chair, and a mirror.
A sign for 'Wilder House' with a maple leaf logo, established in 2023, and a date of 2023.
A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

12. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Mark
S$262
includes taxes & fees
13 Sept - 14 Sept
Wilder House Berkshires
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.

13. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
United States
Andrew
S$284
includes taxes & fees
8 Sept - 9 Sept
Avon Old Farms Hotel
A bedroom with two beds, a desk, a chair, a window with curtains, and a door with a glass panel.
A room with a mounted television, a chair, and a coat rack.
A bathroom with a large mirror, a lighted frame, and a door.
A bathroom with a white sink, a dark wooden vanity, and a drawer with a white towel.

14. Hitching Post Country Motel

Hitching Post Country Motel
Cornwall Bridge
United States
Chris
S$189
includes taxes & fees
8 Sept - 9 Sept
Hitching Post Country Motel
A large, historic building with a covered porch and outdoor seating area.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.
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.

15. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
United States
Brian
S$370
includes taxes & fees
8 Sept - 9 Sept
Simsbury 1820 House
A wooden deck with a swing chair and a bench overlooking a lake.
A tented area with lush greenery and a dining setup.
A modern bar area with a counter, bar stools, and a variety of bottles.
A modern hotel room with a bed, sofa, leather chair, and a small table.

16. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
United States
Stacie
S$279
includes taxes & fees
22 Sept - 23 Sept
Interlaken Inn & Resort
A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.
A spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.
A rustic barn-style venue with round tables and chairs, string lights, and a central bar area.
A wooden sign with "GEDNEY FARM" written on it, surrounded by lush greenery and purple flowers.

17. Gedney Farm

Gedney Farm
Great Barrington
United States
Jane
S$319
includes taxes & fees
8 Sept - 9 Sept
Gedney Farm
A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.
A brick building with a covered patio, a fountain, and a staircase leading to a second floor.
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.

18. Simsbury Inn

Simsbury Inn
Simsbury Center
Canada
Anuj
S$376
includes taxes & fees
16 Sept - 17 Sept
Simsbury Inn
A lobby with a chandelier, a reception desk, and a sign indicating an exit.
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.
A white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

19. The Litchfield Inn

The Litchfield Inn
Litchfield
United States
Sandra
S$412
includes taxes & fees
30 Sept - 1 Oct
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 hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.

20. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
United States
Nancy
S$226
includes taxes & fees
10 Sept - 11 Sept
Hampton Inn & Suites Hartford/Farmington
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winchester attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
See properties

Northwestern Connecticut Community College

Explore the campus of Northwestern Connecticut Community College during your stay in Winchester.
See properties

The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.
See properties

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.
See properties

Platt Hill State Park

You can take time to visit Platt Hill State Park during your travels to Winchester.
See properties

American Mural Project

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

Tatro Pond

You can take time to visit Tatro Pond during your travels to Winchester.
See properties

Walker Field

Explore the great outdoors at Walker Field, a lovely green space in Winchester.
See properties

Top Winchester Hotel Reviews

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

8/10 Good
"Very clean and comfortable!"
Mary 3-night trip
Posted 1 hour ago
Home2 Suites by Hilton Bristol
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Great location."
Nancy 3-night trip
Posted 1 day ago
Hampton Inn & Suites Hartford/Farmington
The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"The Farmington Inn is charming, comfortable and quiet, with an excellent location and easy access to all that CT has to offer."
Rachael Gagner 7-night trip
Posted 2 days ago
The Farmington Inn & Suites
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

8/10 Good
"The room was clean, there was ample free parking and the staff was kind."
MUHAMMAD 2-night trip
Posted 2 days ago
Extended Stay America Suites Hartford Farmington
Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Clean, quiet, great restaurant and pub. Food was over the top delicious!"
Kathryn 1-night trip
Posted 4 days ago
Avon Old Farms Hotel
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Excellent experience all around!"
Allan 2-night trip
Posted 6 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Very nice and charming place to stay. We had a wonderful experience and our kids felt very welcomed and happy."
Angela 1-night trip
Posted 6 days ago
Mayflower Inn & Spa, Auberge Collection
Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"Quaint Inn in a scienic location."
Brian 1-night trip
Posted 7 days ago
Simsbury 1820 House

More cheap stays in Winchester

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
S$142
4 Oct - 5 Oct
includes taxes & fees
Days Inn by Wyndham Torrington
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
S$160
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (1,003 reviews)
Extended Stay America Suites Hartford Farmington
Hitching Post Country Motel

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT
S$189
8 Sept - 9 Sept
includes taxes & fees
6.6/10 (110 reviews)
Hitching Post Country Motel
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT
S$199
20 Sept - 21 Sept
includes taxes & fees
5.6/10 (817 reviews)
Americas Best Value Inn Torrington CT
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT
S$226
10 Sept - 11 Sept
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Hampton Inn & Suites Hartford/Farmington
The Millerton Inn

The Millerton Inn

53 Main St Millerton NY
S$345
8 Oct - 9 Oct
includes taxes & fees
8.4/10 Very good! (37 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 Extended Stay America Suites Hartford Farmington and Homewood Suites by Hilton 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 Fairfield Inn & Suites by Marriott Plainville 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 20 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, Burr Pond State Park and The Marina at Highland Lake. 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.

Explore a world of travel with Expedia