Hotels in Winchester

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Top 5 hotels in Winchester at a glance

1. Days Inn by Wyndham Torrington — 2-star hotel in Torrington. Guest rating: 7.4/10 — Good.
2. Blackberry River Inn — 3-star hotel in Norfolk. Guest rating: 9.4/10 — Exceptional.
3. Locust Tree Bed and Breakfast LLC — 3-star hotel in East Canaan. Guest rating: 8.8/10 — Excellent.
4. Americas Best Value Inn Torrington CT — 2.5-star hotel in Torrington. Guest rating: 5.6/10.
5. Manor House Inn — 3-star hotel in Norfolk. Guest rating: 9.4/10 — Exceptional.

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 Days Inn sign with a sunburst design, surrounded by trees.

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

A Days Inn building with a blue awning, a lobby entrance, and a well-maintained lawn with various plants.

1. Days Inn by Wyndham Torrington

Torrington

$99

$114 total

includes taxes & fees

Oct 4 - Oct 5

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

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.

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

2. Blackberry River Inn

Norfolk

$170

$196 total

includes taxes & fees

Sep 7 - Sep 8

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

A two-story building with a flat roof, solar panels, and a small patio area.

3. Locust Tree Bed and Breakfast LLC

East Canaan

$105

$121 total

includes taxes & fees

Sep 7 - Sep 8

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 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.

4. Americas Best Value Inn Torrington CT

Torrington

$140

$161 total

includes taxes & fees

Sep 6 - Sep 7

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

A cozy room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

5. Manor House Inn

Norfolk

$329

$365 total

includes taxes & fees

Sep 14 - Sep 15

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

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.

6. Truman Gillet House Bed & Breakfast

Granby

$140

$155 total

includes taxes & fees

Sep 7 - Sep 8

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.

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

$225

$259 total

includes taxes & fees

Sep 10 - Sep 11

A spacious foyer with a grand staircase, a chandelier, 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 living room with a patterned sofa, armchairs, a television, and a patterned carpet.

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

8. The Farmington Inn & Suites

Farmington

$149

$189 total

includes taxes & fees

Sep 7 - Sep 8

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 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.

9. Sunny Peace Homestay

Harwinton

$145

$224 total

includes taxes & fees

Sep 7 - Sep 8

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

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.

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

10. Residence Inn by Marriott Hartford Avon

Avon

$144

$165 total

includes taxes & fees

Sep 13 - Sep 14

An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

A modern breakfast area with a counter, seating, and a refrigerator.

A modern hotel building with multiple floors and a prominent "HOME 2 SUITES BY HILTON" sign.

A large indoor swimming pool with multiple seating areas and large windows.

11. Home2 Suites by Hilton Bristol

Bristol

$130

$150 total

includes taxes & fees

Sep 20 - Sep 21

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 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.

12. Simsbury 1820 House

Simsbury Center

$239

$292 total

includes taxes & fees

Sep 8 - Sep 9

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

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

A heart-shaped bathtub with a single faucet and a drain.

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

13. PLYMOUTH MOTOR LODGE

Terryville

$89

$102 total

includes taxes & fees

Sep 7 - Sep 8

A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

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.

A spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.

14. Gedney Farm

Great Barrington

$243

$267 total

includes taxes & fees

Sep 7 - Sep 8

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

A bedroom with a large bed, a dresser, a chair, and a mirror.

15. Wilder House Berkshires

Sheffield

$223

$249 total

includes taxes & fees

Sep 10 - Sep 11

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

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.

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

16. Hampton Inn & Suites Hartford/Farmington

Farmington

$138

$159 total

includes taxes & fees

Sep 10 - Sep 11

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

A tented area with lush greenery and a dining setup.

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.

17. Interlaken Inn & Resort

Lakeville

$203

$234 total

includes taxes & fees

Sep 22 - Sep 23

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

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

18. Avon Old Farms Hotel

Avon

$176

$224 total

includes taxes & fees

Sep 7 - Sep 8

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.

A sign for The Simsbury Inn, featuring a swan on water.

19. Simsbury Inn

Simsbury Center

$239

$297 total

includes taxes & fees

Sep 16 - Sep 17

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

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

20. The Litchfield Inn

Litchfield

$309

$355 total

includes taxes & fees

Sep 14 - Sep 15

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Go beyond your typical stay in Winchester

Pet friendly

Spa

Pool

Hot tub

Family friendly

Cottage

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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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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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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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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Platt Hill State Park

Platt Hill State Park is 2.4 mi (3.8 km) from central Winchester, why not stop by during your stay.

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Tatro Pond

Tatro Pond is 2.5 mi (4.1 km) from central Winchester, why not stop by during your stay.

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Walker Field

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

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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, Burr Pond State Park, and Northwestern Connecticut Community College.

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Check out reviews of Winchester hotels guests love

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"Excellent experience all around!"

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."

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent

"Parking , staff & breakfast 5 stars!"

Simsbury 1820 House

10/10 Excellent

"Quaint Inn in a scienic location."

Days Inn by Wyndham Torrington

10/10 Excellent

"None"

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent

"nons"

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 10 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.

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