Top 10 Hotels in Winchester, CT (from $97) 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 bathroom with a bathtub, toilet, and granite countertop sink.

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

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

Alyson

$84 nightly

$97 total

Oct 25 - Oct 26

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

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.

2. Americas Best Value Inn Torrington CT

Torrington

Carol

$136 nightly

$156 total

Oct 3 - Oct 4

Total with taxes and fees

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 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.

3. Blackberry River Inn

Norfolk

Brian

$160 nightly

$184 total

Oct 4 - Oct 5

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 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

Kevin

$325 nightly

$360 total

Oct 4 - Oct 5

Total with taxes and fees

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

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

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.

5. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

$105 nightly

$121 total

Oct 4 - Oct 5

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 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.

A house with a garden featuring purple flowers and a stone wall.

6. Sunny Peace Homestay

Harwinton

Dean

$195 nightly

$224 total

Oct 5 - Oct 6

Total with taxes and fees

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

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.

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

Melanie

$140 nightly

$155 total

Oct 11 - Oct 12

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 bathroom with a white sink, a dark wooden vanity, and a drawer with a white towel.

A room with a mounted television, a chair, and a coat rack.

A bathroom with a large mirror, a lighted frame, and a door.

8. Hitching Post Country Motel

Cornwall Bridge

Chris

$130 nightly

$150 total

Oct 3 - Oct 4

Total with taxes and fees

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

An outdoor seating area with green chairs and tables, a bar with shelves of bottles, and a view of trees in the background.

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.

9. The Abner Hotel

Litchfield Historic District

Ann S

$194 nightly

$223 total

Nov 1 - Nov 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 breakfast area with a counter, seating, and a refrigerator.

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.

10. Home2 Suites by Hilton Bristol

Bristol

Gabriela

$130 nightly

$150 total

Nov 1 - Nov 2

Total with taxes and fees

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

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.

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

11. Interlaken Inn & Resort

Lakeville

Stacie

$212 nightly

$243 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

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

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

12. Hampton Inn & Suites Hartford/Farmington

Farmington

Liam

$144 nightly

$165 total

Oct 31 - Nov 1

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.

13. Wilder House Berkshires

Sheffield

Mark

$206 nightly

$231 total

Oct 25 - Oct 26

Total with taxes and fees

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 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.

14. The Litchfield Inn

Litchfield

Wei

$300 nightly

$345 total

Nov 2 - Nov 3

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

15. Residence Inn by Marriott Hartford Avon

Avon

Laura

$144 nightly

$165 total

Nov 1 - Nov 2

Total with taxes and fees

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.

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

A wooden sign with "GEDNEY FARM" written on it, surrounded by lush greenery and purple flowers.

16. Gedney Farm

Great Barrington

Terri

$184 nightly

$202 total

Nov 2 - Nov 3

Total with taxes and fees

A spacious foyer with a grand staircase, a chandelier, 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.

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.

17. The Farmington Inn & Suites

Farmington

Brian

$137 nightly

$158 total

Nov 2 - Nov 3

Total with taxes and fees

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

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.

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

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

18. DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

DARRON

$162 nightly

$186 total

Oct 18 - Oct 19

Total with taxes and fees

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

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

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

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

19. PLYMOUTH MOTOR LODGE

Terryville

SEMORA

$89 nightly

$102 total

Oct 4 - Oct 5

Total with taxes and fees

A lobby with a blue sofa, a small round table, and a fireplace.

A Fairfield Inn & Suites hotel with a large parking lot and snow-covered ground.

An indoor swimming pool with a 'No Diving' sign, a glass enclosure, and a tiled wall with a 'No Diving' sign.

A hotel reception area with a wooden reception desk, a minibar, and a wall-mounted decorative panel.

20. Fairfield Inn & Suites by Marriott Plainville

Plainville

ERIK

$122 nightly

$141 total

Nov 1 - Nov 2

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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The Marina at Highland Lake

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

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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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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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American Mural Project

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

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Northwestern Connecticut Community College Library

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

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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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Rowley Fields

Explore the great outdoors at Rowley Fields, a lovely green space in Winchester.

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Top Winchester Hotel Reviews

Simsbury 1820 House

10/10 Excellent

"My mom and I were traveling to Maine and stopped here for a night along the way. What a wonderful property, the room was absolutely lovely and the staff was so friendly and accommodating. We ate at the restaurant on site and it was fabulous. Well forwarded to visiting again and staying here."

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."

The Abner Hotel

10/10 Excellent

"We loved our stay- the room was so well presented/had everything we could need, and we felt so well looked after by all staff. We enjoyed the breakfast, and drinks on the rooftop bar were definitely a highlight! We had dinner one out of the two nights we were staying, which was also lovely. Highly recommend if you’re in the Litchfield area!"

Avon Old Farms Hotel

8/10 Good

"The hotel is a classic, but it needs some upgrades and maintenance. The window openers are falling apart. It needs more outlets for chargers. The toilets should be upgraded to comfort height. The bar is magnificent as is the food. The phones are not answered quickly enough which indicates a lack of sufficient staff."

Sheraton Hartford Hotel at Bradley Airport

8/10 Good

"Everything was great and of course it’s connected to the airport so very easy. However I had a handicapped accessible bath"

Home2 Suites by Hilton Bristol

10/10 Excellent

"Property was very clean and well maintained. The first thing that caught my attention was how good it smelled almost reminds you of a newer property. Staff was very friendly amenities were great very pleasant day."

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent

"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

10/10 Excellent

"Pet friendly beautiful clean house on lake. Host is very easy to work with."

More cheap stays in Winchester

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

$84 nightly

$97 total

Oct 25 - Oct 26

Total with taxes and fees

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

$128 nightly

$147 total

Oct 20 - Oct 21

Total with taxes and fees

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT

$130 nightly

$150 total

Oct 3 - Oct 4

Total with taxes and fees

6.6/10 (112 reviews)

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

$136 nightly

$156 total

Oct 3 - Oct 4

Total with taxes and fees

5.6/10 (822 reviews)

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT

$144 nightly

$165 total

Oct 31 - Nov 1

Total with taxes and fees

The Millerton Inn

53 Main St Millerton NY

$279 nightly

$316 total

Oct 4 - Oct 5

Total with taxes and fees

8.4/10 Very Good! (45 reviews)

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 $97 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 $97

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. Americas Best Value Inn Torrington CT

3. Blackberry River Inn

4. Manor House Inn

5. Locust Tree Bed and Breakfast LLC

6. Sunny Peace Homestay

7. Truman Gillet House Bed & Breakfast

8. Hitching Post Country Motel

9. The Abner Hotel

10. Home2 Suites by Hilton Bristol

11. Interlaken Inn & Resort

12. Hampton Inn & Suites Hartford/Farmington

13. Wilder House Berkshires

14. The Litchfield Inn

15. Residence Inn by Marriott Hartford Avon

16. Gedney Farm

17. The Farmington Inn & Suites

18. DoubleTree by Hilton Hotel Bristol, Connecticut

19. PLYMOUTH MOTOR LODGE

20. Fairfield Inn & Suites by Marriott Plainville

Stay near popular Winchester attractions

Highland Lake

The Marina at Highland Lake

Northwestern Connecticut Community College

Winchester Historical Society

American Mural Project

Northwestern Connecticut Community College Library

Platt Hill State Park

Rowley Fields

Top Winchester Hotel Reviews

Simsbury 1820 House

Interlaken Inn & Resort

The Abner Hotel

Avon Old Farms Hotel

Sheraton Hartford Hotel at Bradley Airport

Home2 Suites by Hilton Bristol

Mayflower Inn & Spa, Auberge Collection

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

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

Hotels in Winchester with star-rating

Frequently asked questions

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