Top 10 Hotels in Winchester, CT (from $98) 2026 - Competitive Prices

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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 sign with a sunburst design, surrounded by trees.

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

A kitchen area with a counter, a microwave, a coffee machine, and a display case with pastries.

1. Days Inn by Wyndham Torrington

Torrington

Juan

$100 nightly

$115 total

Sep 2 - Sep 3

Total with taxes and fees

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 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.

2. Blackberry River Inn

Norfolk

Rachel

$171 nightly

$197 total

Sep 30 - Oct 1

Total with taxes and fees

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 covered porch with white railings and rocking chairs.

3. Locust Tree Bed and Breakfast LLC

East Canaan

Regina

$105 nightly

$121 total

Aug 31 - Sep 1

Total with taxes and fees

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.

4. Americas Best Value Inn Torrington CT

Torrington

Carol

$130 nightly

$149 total

Aug 31 - Sep 1

Total with taxes and fees

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

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

5. Manor House Inn

Norfolk

Kevin

$286 nightly

$318 total

Sep 29 - Sep 30

Total with taxes and fees

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.

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.

6. The Abner Hotel

Litchfield Historic District

Eduardo

$159 nightly

$183 total

Sep 20 - Sep 21

Total with taxes and fees

A house with a porch, American flags, and a pathway leading to a bench.

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.

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.

7. Truman Gillet House Bed & Breakfast

Granby

Valerie

$140 nightly

$155 total

Sep 1 - Sep 2

Total with taxes and fees

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

Harwinton

Dean

$179 nightly

$206 total

Sep 7 - Sep 8

Total with taxes and fees

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 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.

9. Simsbury 1820 House

Simsbury Center

Thomas

$184 nightly

$212 total

Aug 31 - Sep 1

Total with taxes and fees

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 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.

10. Hitching Post Country Motel

Cornwall Bridge

Chris

$130 nightly

$150 total

Aug 31 - Sep 1

Total with taxes and fees

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

A hotel lobby with a long reception desk, multiple seating areas, and a large screen TV.

11. Residence Inn by Marriott Hartford Avon

Avon

Laura

$152 nightly

$175 total

Sep 13 - Sep 14

Total with taxes and fees

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 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.

12. Avon Old Farms Hotel

Avon

Andrew

$191 nightly

$219 total

Sep 7 - Sep 8

Total with taxes and fees

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

13. PLYMOUTH MOTOR LODGE

Terryville

SEMORA

$85 nightly

$98 total

Sep 8 - Sep 9

Total with taxes and fees

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.

14. Wilder House Berkshires

Sheffield

Jennifer

$206 nightly

$231 total

Sep 13 - Sep 14

Total with taxes and fees

A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

A wooden counter with a wine bottle, glasses, and a sign.

A two-story building with a sign for Cornwall Inn, featuring a front porch and a mailbox.

A hotel room with a large bed, two bedside lamps, a chair, a small table, and a rug.

15. Cornwall Inn and Lodge

Cornwall Bridge

"Liked we had a room away from the main building which was quiet and had a private porch. Charming decor with antiques. We really enjoyed the breakfast room and meeting the other guests in the morning and exchanging information on local sites and restaurants. The pool was very refreshing after a hot day. We loved sitting on the porch for breakfast and evening drinks. Getting AC to run consistently was a challenge."

Judith

$212 nightly

$243 total

Aug 31 - Sep 1

Total with taxes and fees

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

An outdoor patio with wooden tables and chairs, surrounded by greenery.

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.

16. Gedney Farm

Great Barrington

Jane

$241 nightly

$264 total

Sep 7 - Sep 8

Total with taxes and fees

A lobby with a chandelier, a reception desk, and a sign indicating an exit.

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.

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

17. The Litchfield Inn

Litchfield

Sandra

$291 nightly

$335 total

Aug 31 - Sep 1

Total with taxes and fees

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 bar area with a counter, bar stools, and a variety of bottles.

18. Interlaken Inn & Resort

Lakeville

Stacie

$222 nightly

$255 total

Sep 20 - Sep 21

Total with taxes and fees

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 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.

19. The Farmington Inn & Suites

Farmington

Carol

$143 nightly

$165 total

Sep 1 - Sep 2

Total with taxes and fees

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

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

A modern lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.

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

20. Home2 Suites by Hilton Bristol

Bristol

Laura

$130 nightly

$150 total

Sep 20 - Sep 21

Total with taxes and fees

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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

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

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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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Platt Hill State Park

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

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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.

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Walker Field

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

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American Mural Project

You can spend time studying the exhibits at American Mural Project in Winchester.

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Tatro Pond

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

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Top Winchester Hotel Reviews

The Farmington Inn & Suites

8/10 Good

"Nice older hotel with a lot of charm. Some updates could be nice, but it is fine as it is. Reasonable price."

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent

"nons"

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent

"The staff was very accommodating and the breakfast was delicious. Lots of choices and always enough available."

The Litchfield Inn

10/10 Excellent

"Charming older hotel. Wish there were more tv options"

The Abner Hotel

10/10 Excellent

"I think this hotel would be wonderful in any season...beautiful area to walk on the wide, stately streets with beautiful 1800's home in the summer, spring or fall; lots of beautiful autumn leaves in the fall, perfect New England town with center green in winter, summer, spring and fall, to beautiful spring with flowers all over the town too. At Abner Hotel you can enjoy any season with the great rooftop bar, the cozy fireplace in the lounge outside the restaurant in the winter.... A special attraction for attorneys or anyone interested in the law is the unique nature of this property which was a renovated and preserved old courthouse.... Don't forget the fascinating attraction of country's very first Law School, walking distance from the hotel! Lourdes of Litchfield Grotto, lovely with outdoor masses, stations of the cross, gift shop and Cafe, open to all, just down the road."

Simsbury 1820 House

10/10 Excellent

"The staff at Simsbury 1820 were the highlight of the stay. They were expecially friendly and very helpful. They had some suggestions of things to do that were interesting and area specific. Understandably but a bit disappointing was the inadquacy of the plumbing. It's a very old building but toilets could be updated."

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent

"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared to be a utility room that was active early in the morning. I could hear footsteps throughout the day. The dinner was overrated, but the breakfast and lunch were delicious."

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT

$85 nightly

$98 total

Sep 8 - Sep 9

Total with taxes and fees

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

$100 nightly

$115 total

Sep 2 - Sep 3

Total with taxes and fees

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

$110 nightly

$126 total

Sep 1 - Sep 2

Total with taxes and fees

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

$130 nightly

$149 total

Aug 31 - Sep 1

Total with taxes and fees

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT

$130 nightly

$150 total

Aug 31 - Sep 1

Total with taxes and fees

6.8/10 (109 reviews)

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT

$139 nightly

$159 total

Sep 7 - Sep 8

Total with taxes and fees

Hotels in Winchester with star-rating

Frequently asked questions

What is the best area to stay in Winchester?

The best area to stay in Winchester, Connecticut, is the town center, particularly around Main Street and the historic district of Winsted.Winsted's town center is the heart of Winchester, offering a blend of historic architecture and local amenities. Main Street is lined with local shops, eateries, and public buildings, and the area is home to the beautiful Highland Lake. This district provides a central and convenient base for exploring the town.For couples looking for a relaxed getaway, staying near Highland Lake offers scenic views and opportunities for outdoor activities like kayaking or enjoying a lakeside stroll. The proximity to local restaurants and unique shops along Main Street makes for enjoyable evenings.Travelers interested in the town's history will appreciate accommodation within the historic district of Winsted.

When is the best time to go to Winchester?

The best time to visit Winchester, Connecticut, is during the summer months, from June to August, or in the fall, from September to October.Summer offers ideal weather for outdoor activities, with warm temperatures superb for exploring the Winchester Lake State Park. You can enjoy boating, fishing, and hiking around the lake, making it a great time for families looking for recreational opportunities. The area around Main Street in Winsted, the borough within Winchester, also has local events and markets during this period.For couples or travelers who appreciate cooler weather and scenic beauty, the fall foliage season is spectacular. The surrounding Litchfield Hills transform with vibrant colors, providing a picturesque backdrop for drives and walks.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.

How much is the nightly rate at a Winchester hotel?

Prices for hotels in Winchester often vary, but you can find a great deal from $98 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia

Lodging

Find hotels in Winchester, CT from $98

Upfront pricing

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. Locust Tree Bed and Breakfast LLC

4. Americas Best Value Inn Torrington CT

5. Manor House Inn

6. The Abner Hotel

7. Truman Gillet House Bed & Breakfast

8. Sunny Peace Homestay

9. Simsbury 1820 House

10. Hitching Post Country Motel

11. Residence Inn by Marriott Hartford Avon

12. Avon Old Farms Hotel

13. PLYMOUTH MOTOR LODGE

14. Wilder House Berkshires

15. Cornwall Inn and Lodge

16. Gedney Farm

17. The Litchfield Inn

18. Interlaken Inn & Resort

19. The Farmington Inn & Suites

20. Home2 Suites by Hilton Bristol

Stay near popular Winchester attractions

Highland Lake

Northwestern Connecticut Community College

The Marina at Highland Lake

Platt Hill State Park

Winchester Historical Society

Walker Field

American Mural Project

Tatro Pond

Top Winchester Hotel Reviews

The Farmington Inn & Suites

Homewood Suites by Hilton Hartford-Farmington

Fairfield Inn & Suites by Marriott Plainville

The Litchfield Inn

The Abner Hotel

Simsbury 1820 House

Mayflower Inn & Spa, Auberge Collection

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

Days Inn by Wyndham Torrington

Extended Stay America Suites Hartford Farmington

Americas Best Value Inn Torrington CT

Hitching Post Country Motel

Hampton Inn & Suites Hartford/Farmington

Hotels in Winchester with star-rating

Frequently asked questions

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