A mountain lake surrounded by dense forests and rocky shores.

Hotels in Winchester

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Where to stay in Winchester?

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 bathroom with a bathtub, toilet, and granite countertop sink.

1. Days Inn by Wyndham Torrington

Torrington

$85

$98 total

includes taxes & fees

Nov 12 - Nov 13

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

2. Blackberry River Inn

Norfolk

$190

$219 total

includes taxes & fees

Oct 20 - Oct 21

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".

3. Americas Best Value Inn Torrington CT

Torrington

$150

$172 total

includes taxes & fees

Oct 20 - Oct 21

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.

4. Manor House Inn

Norfolk

$349

$387 total

includes taxes & fees

Oct 20 - Oct 21

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

A covered porch with white railings and rocking chairs.

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

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

5. Locust Tree Bed and Breakfast LLC

East Canaan

$105

$121 total

includes taxes & fees

Oct 20 - Oct 21

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 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.

6. Sunny Peace Homestay

Harwinton

$145

$224 total

includes taxes & fees

Oct 20 - Oct 21

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

Litchfield Historic District

$228

$262 total

includes taxes & fees

Nov 8 - Nov 9

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 living room with a fireplace, a wooden cabinet, a plaid sofa, and a patterned rug.

A wooden desk with a notebook, two mugs, a framed sign, a telephone, and a decorative bowl.

8. Truman Gillet House Bed & Breakfast

Granby

$140

$155 total

includes taxes & fees

Oct 20 - Oct 21

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.

9. Belden House & Mews

Litchfield Historic District

$455

$563 total

includes taxes & fees

Nov 1 - Nov 2

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.

10. Home2 Suites by Hilton Bristol

Bristol

$130

$150 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.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and large windows offering a view of greenery outside.

11. Hampton Inn & Suites Hartford/Farmington

Farmington

$144

$165 total

includes taxes & fees

Oct 30 - Oct 31

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.

12. The Old Inn On The Green

Great Barrington

$290

$350 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

13. Simsbury 1820 House

Simsbury Center

$174

$218 total

includes taxes & fees

Nov 19 - Nov 20

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 white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

A rustic bedroom with a large bed, wooden headboard, and a wooden floor. There is a chair and a small table with a lamp.

14. The Litchfield Inn

Litchfield

$289

$332 total

includes taxes & fees

Nov 15 - Nov 16

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 stone fireplace with a flat-screen TV above it, surrounded by two chairs and a small table.

15. Residence Inn by Marriott Hartford Avon

Avon

$135

$155 total

includes taxes & fees

Nov 19 - Nov 20

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

16. Wilder House Berkshires

Sheffield

$164

$183 total

includes taxes & fees

Nov 2 - Nov 3

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 well-lit room with a fireplace, two armchairs, a sofa, and a coffee table.

A spacious lobby with a patterned rug, a potted plant, and a television.

17. The Farmington Inn & Suites

Farmington

$139

$177 total

includes taxes & fees

Nov 8 - Nov 9

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

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

18. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

$147

$169 total

includes taxes & fees

Nov 8 - Nov 9

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

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

19. Avon Old Farms Hotel

Avon

$176

$224 total

includes taxes & fees

Nov 17 - Nov 18

A hotel room with two beds, a nightstand with a lamp, and a wall-mounted phone.

A hotel room with a kitchenette, a desk, a chair, a mirror, and a door.

A bathroom with a shower, toilet, and towel rack.

A motel with a sign reading "Plymouth Motor Lodge".

20. PLYMOUTH MOTOR LODGE

Terryville

$89

$102 total

includes taxes & fees

Oct 20 - Oct 21

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Go beyond your typical stay in Winchester

Top landmarks in Winchester

Highland Lake

Highland Lake is 2.6 mi (4.3 km) from central Winchester, why not stop by during your stay.

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The Marina at Highland Lake

Imagine strolling along The Marina at Highland Lake for some great waterfront pics. It's located 1.8 mi (2.9 km) from central Winchester.

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Northwestern Connecticut Community College

If you'd like to get a taste of Winchester student life, check out Northwestern Connecticut Community College, in the heart of the town.

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Winchester Historical Society

8.0/10 (1 review)

You might want to get your camera out and head to Winchester Historical Society— just one of the landmarks located 1.9 mi (3.1 km) from central Winchester.

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Northwestern Connecticut Community College Library

Northwestern Connecticut Community College Library is worth a visit when in central Winchester.

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Rowley Fields

If you like quiet time surrounded by flowers and greenery, then make a stop at Rowley Fields in the heart of Winchester. Want to stretch your legs some more? Head to Walker Field, just a short walk away.

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Ledgebrook Plaza

If you like shopping, take time out to go to Ledgebrook Plaza when in Winchester. Splash some more cash at Ames Plaza Shopping Center.

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American Mural Project

The center of Winchester is home to cultural attractions like American Mural Project, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Highland Lake, The Village, and Northwestern Connecticut Community College.

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Check out reviews of Winchester hotels guests love

Blackberry River Inn

Norfolk

10/10 Exceptional

Emily

Manor House Inn

Norfolk

10/10 Exceptional

Kyle

Days Inn by Wyndham Torrington

Torrington

10/10 Exceptional

Allen

Locust Tree Bed and Breakfast LLC

East Canaan

10/10 Exceptional

rose

The Abner Hotel

Litchfield Historic District

10/10 Exceptional

Karen

Truman Gillet House Bed & Breakfast

Granby

10/10 Exceptional

Christine

Wilder House Berkshires

Sheffield

10/10 Exceptional

joseph

Sunny Peace Homestay

Harwinton

10/10 Exceptional

GREGORY

Home2 Suites by Hilton Bristol

Bristol

10/10 Exceptional

Michelle

Simsbury 1820 House

Simsbury Center

10/10 Exceptional

Warren

The Litchfield Inn

Litchfield

10/10 Exceptional

Anonymous traveler

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

A covered porch with a dining area, a sofa, and decorative wall art.

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

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

The White Hart

Salisbury

10/10 Exceptional

We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our...

thomas

The Old Inn On The Green

Great Barrington

10/10 Exceptional

Rishi

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

A hotel lobby with a fireplace, seating area, and decorative wall sconces.

Delamar West Hartford

West Hartford

10/10 Exceptional

elizabeth

Hampton Inn & Suites Hartford/Farmington

Farmington

10/10 Exceptional

Debora D.

A modern kitchen with a dining area, a large window, and a view of the garden.

A modern outdoor dining area with a round table and white chairs, surrounded by lush greenery and a white railing.

A modern kitchen with a wooden dining table, chairs, a pendant light, and a black countertop with a coffee maker and a plant.

A white building with a number '9' sign, a covered entrance, and six planters with shrubs.

9 Academy

Salisbury

10/10 Exceptional

Louise

Frequently Asked Questions

What hotels do travelers recommend in Winchester?

Guests like Days Inn by Wyndham Torrington and Americas Best Value Inn Torrington CT.

Can I book refundable accommodations in Winchester?

If you want the flexibility to change your plans to Winchester, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Winchester if I want a vacation rental instead of a hotel?

If you're looking for a good alternative to a hotel, browse our selection of 11 vacation homes. In addition, you can choose from 5 apartments.

What will the weather in Winchester be like during my vacation?

July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 30°F. July and October are the months with the most rain.

Why should I book my Winchester hotel with Hotels.com?

There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.