Top 10 Hotels in Winchester, CT from ₩132,320 - Competitive Prices

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

Go beyond your typical stay in Winchester

Pet friendly

Apartment

Pool

Family friendly

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

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 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.

1. Days Inn by Wyndham Torrington

Torrington

Alyson

₩115,061

₩132,320 total

includes taxes & fees

Oct 18 - Oct 19

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 cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

A room with a fireplace, two striped armchairs, and a floral drape.

2. Blackberry River Inn

Norfolk

Donna

₩254,649

₩292,847 total

includes taxes & fees

Oct 13 - Oct 14

A patio with a round metal table, a glass of white wine, and a red umbrella.

A grand staircase with a wooden railing, leading to a room with large windows and a patterned ceiling.

A large, two-story house with a steeply pitched roof, stone foundation, and a well-maintained garden with various shrubs and a fountain.

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.

3. Manor House Inn

Norfolk

Kevin

₩467,751

₩519,203 total

includes taxes & fees

Oct 19 - Oct 20

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 gym with various exercise equipment, a mirror, and a blue wall.

A motel with a covered entrance, a parking lot, and a building with a sign that reads "LARRY'S".

4. Americas Best Value Inn Torrington CT

Torrington

Carol

₩182,262

₩209,602 total

includes taxes & fees

Oct 11 - Oct 12

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 spacious living room with a fireplace, a dining area, and a sofa.

A long wooden table with potted plants and candle holders in a modern interior setting.

5. The Litchfield Inn

Litchfield

Wei

₩416,027

₩478,431 total

includes taxes & fees

Nov 2 - Nov 3

A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

An outdoor patio area with wooden flooring, green metal chairs, and tables under umbrellas.

A hotel room with a bed, a sofa, a small table, a floor lamp, and two windows with curtains.

A spacious foyer with a wooden staircase, a reception desk, and a seating area.

6. The Abner Hotel

Litchfield Historic District

JANET

₩305,914

₩351,805 total

includes taxes & fees

Nov 1 - Nov 2

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A covered porch with white railings and rocking chairs.

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

7. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

₩140,727

₩161,836 total

includes taxes & fees

Oct 11 - Oct 12

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 person in a blue swimsuit relaxing in a hot tub with a pool in the background.

A large, multi-story building surrounded by dense forest, with a parking lot and a small green structure nearby.

8. Simsbury Inn

Simsbury Center

Kristen

₩387,335

₩474,720 total

includes taxes & fees

Oct 12 - Oct 13

A wooden deck with a swing chair and a bench overlooking a lake.

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.

A tented area with lush greenery and a dining setup.

9. Interlaken Inn & Resort

Lakeville

Stacie

₩324,477

₩373,149 total

includes taxes & fees

Oct 26 - Oct 27

A large, historic building with a covered porch and outdoor seating area.

A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.

A sign for the Simsbury House, indicating it is a historic building from 1820.

A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.

10. Simsbury 1820 House

Simsbury Center

Kimberly

₩234,795

₩293,133 total

includes taxes & fees

Nov 4 - Nov 5

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

A swimming pool with lounge chairs and a covered seating area, surrounded by multi-story buildings with visible windows and a brick facade.

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.

11. Residence Inn by Marriott Hartford Avon

Avon

RAE

₩192,528

₩221,407 total

includes taxes & fees

Nov 1 - Nov 2

A hotel with a prominent sign, a covered entrance, and a landscaped driveway.

A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.

An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.

A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

12. Hampton Inn & Suites Hartford/Farmington

Farmington

Jessica

₩214,174

₩246,300 total

includes taxes & fees

Nov 1 - Nov 2

A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.

A large conference room with multiple round tables, beige chairs, chandeliers, and a wooden floor.

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

A spacious indoor dining area with high ceilings, large windows, and a brick wall.

13. Avon Old Farms Hotel

Avon

William

₩258,241

₩326,260 total

includes taxes & fees

Oct 14 - Oct 15

A bedroom with a large bed, a chair, and a window with curtains.

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 dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

14. The White Hart

Salisbury

William

₩1,210,255

₩1,391,793 total

includes taxes & fees

Oct 24 - Oct 25

An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

A modern lobby with a reception desk, seating area, and a large decorative light fixture.

A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.

A spacious lobby with large windows, a central plant, and multiple hanging lights.

15. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

Carroll

₩208,014

₩239,216 total

includes taxes & fees

Oct 29 - Oct 30

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 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.

16. The Farmington Inn & Suites

Farmington

Brian

₩186,296

₩237,359 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

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.

17. The Old Inn On The Green

Great Barrington

Catherine

₩388,675

₩469,010 total

includes taxes & fees

Nov 1 - Nov 2

A large, two-story house with a wrap-around porch, a central entrance, and a flag.

A modern house with a white exterior, two wooden doors, and a grey awning.

A dining area with a round table, chairs, a fireplace, and a variety of plants.

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.

18. Belden House & Mews

Litchfield Historic District

₩609,818

₩754,901 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor dining area with tables and chairs, surrounded by plants and trees.

A restaurant with a brick floor, wooden chairs, and tables. There is a bar area with bottles and glasses.

A spacious lobby with a reception desk, seating area, and a large, round, woven coffee table.

A multi-level interior with a grand staircase, a chandelier, and a checkered floor.

19. Delamar West Hartford

West Hartford

Sarah

₩475,710

₩573,871 total

includes taxes & fees

Nov 1 - Nov 2

A hotel with multiple buildings, a parking lot, and a well-maintained lawn.

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.

A modern lobby with a yellow sofa, marble table, and two armchairs.

20. Homewood Suites by Hilton Hartford-Farmington

Farmington

John

₩226,705

₩260,711 total

includes taxes & fees

Oct 25 - Oct 26

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

The Marina at Highland Lake

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

See properties

Northwestern Connecticut Community College

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

See properties

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.

See properties

Northwestern Connecticut Community College Library

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

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 studying the exhibits at American Mural Project in Winchester.

See properties

Tatro Pond

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

See properties

Top Winchester Hotel Reviews

Home2 Suites by Hilton Bristol

8/10 Good

"Bed was not very comfortable."

The Litchfield Inn

10/10 Excellent

"Wonderful stay! Beautiful property and pool, breakfast was delicious."

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent

"Nice place close to west Hartford. Staff was helpful."

Sheraton Hartford Hotel at Bradley Airport

8/10 Good

"Convience"

Simsbury 1820 House

10/10 Excellent

"Lovely comfortable place!!"

Delamar West Hartford

10/10 Excellent

"The staff was amazing. Super helpful and kind. The room was one of the most beautiful and elegant places we’ve stayed at and the hotel amenities, and restaurant was just something I’ll never forget. Thank you for this experience!"

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

Troutbeck

10/10 Excellent

"Absolutely stunning escape. Just go"

Belden House & Mews

10/10 Excellent

"Our stay was outstanding. Comforting and convenient. We hope to make another staycation there again"

More cheap stays in Winchester

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

₩115,061

₩132,320 total

Oct 18 - Oct 19

includes taxes & fees

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

₩162,962

₩187,407 total

Nov 1 - Nov 2

includes taxes & fees

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT

₩174,234

₩200,369 total

Oct 12 - Oct 13

includes taxes & fees

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

₩182,262

₩209,602 total

Oct 11 - Oct 12

includes taxes & fees

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT

₩214,174

₩246,300 total

Nov 1 - Nov 2

includes taxes & fees

The Millerton Inn

53 Main St Millerton NY

₩336,539

₩380,714 total

Oct 13 - Oct 14

includes taxes & fees

8.4/10 Very Good! (46 reviews)

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.

Explore a world of travel with Expedia

Car rental Washington

Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, CT from ₩132,320

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Days Inn by Wyndham Torrington

2. Blackberry River Inn

3. Manor House Inn

4. Americas Best Value Inn Torrington CT

5. The Litchfield Inn

6. The Abner Hotel

7. Locust Tree Bed and Breakfast LLC

8. Simsbury Inn

9. Interlaken Inn & Resort

10. Simsbury 1820 House

11. Residence Inn by Marriott Hartford Avon

12. Hampton Inn & Suites Hartford/Farmington

13. Avon Old Farms Hotel

14. The White Hart

15. DoubleTree by Hilton Hotel Bristol, Connecticut

16. The Farmington Inn & Suites

17. The Old Inn On The Green

18. Belden House & Mews

19. Delamar West Hartford

20. Homewood Suites by Hilton Hartford-Farmington

Stay near popular Winchester attractions

Highland Lake

The Marina at Highland Lake

Northwestern Connecticut Community College

Winchester Historical Society

Northwestern Connecticut Community College Library

Platt Hill State Park

American Mural Project

Tatro Pond

Top Winchester Hotel Reviews

Home2 Suites by Hilton Bristol

The Litchfield Inn

Homewood Suites by Hilton Hartford-Farmington

Sheraton Hartford Hotel at Bradley Airport

Simsbury 1820 House

Delamar West Hartford

Interlaken Inn & Resort

Troutbeck

Belden House & Mews

More cheap stays in Winchester

Days Inn by Wyndham Torrington

Extended Stay America Suites Hartford Farmington

Hitching Post Country Motel

Americas Best Value Inn Torrington CT

Hampton Inn & Suites Hartford/Farmington

The Millerton Inn

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app