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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 breakfast bar with a coffee machine, toaster, and various food items.
A Days Inn sign with a sunburst design, surrounded by trees.

1. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
Torrington
United States
Alyson
$86 nightly
$99 total
Oct 18 - Oct 19
Total with taxes and fees
Days Inn by Wyndham Torrington
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.
Lobby

2. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
Torrington
United States
Carol
$136 nightly
$156 total
Oct 11 - Oct 12
Total with taxes and fees
Americas Best Value Inn Torrington CT
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 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.

3. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Donna
$190 nightly
$219 total
Oct 13 - Oct 14
Total with taxes and fees
Blackberry River Inn
A patio with a round metal table, a glass of white wine, and a red umbrella.
A cozy room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
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.

4. Manor House Inn

Manor House Inn
Norfolk
United States
Kevin
$290 nightly
$322 total
Oct 21 - Oct 22
Total with taxes and fees
Manor House Inn
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 covered porch with white railings and rocking chairs.
A two-story building with a flat roof, solar panels, and a small patio area.

5. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Daniel
$105 nightly
$121 total
Oct 11 - Oct 12
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
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 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

Sunny Peace Homestay
Harwinton
United States
Dean
$195 nightly
$224 total
Oct 12 - Oct 13
Total with taxes and fees
Sunny Peace Homestay
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.
An outdoor patio area with wooden flooring, green metal chairs, and tables under umbrellas.

7. The Abner Hotel

The Abner Hotel
Litchfield Historic District
United States
JANET
$228 nightly
$262 total
Nov 1 - Nov 2
Total with taxes and fees
The Abner Hotel
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 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 wooden desk with a notebook, two mugs, a framed sign, a telephone, and a decorative bowl.

8. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
Granby
United States
Melanie
$140 nightly
$155 total
Oct 18 - Oct 19
Total with taxes and fees
Truman Gillet House Bed & Breakfast
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

9. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
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 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.

10. The Farmington Inn & Suites

The Farmington Inn & Suites
Farmington
United States
Brian
$129 nightly
$148 total
Nov 9 - Nov 10
Total with taxes and fees
The Farmington Inn & Suites
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 motel with a sign reading "Plymouth Motor Lodge".
A bathroom with a shower, toilet, and towel rack.

11. PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
Terryville
United States
SEMORA
$89 nightly
$102 total
Oct 12 - Oct 13
Total with taxes and fees
PLYMOUTH MOTOR LODGE
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.

12. The Litchfield Inn

The Litchfield Inn
Litchfield
Canada
Wei
$310 nightly
$357 total
Nov 2 - Nov 3
Total with taxes and fees
The Litchfield Inn
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.
An outdoor patio with tables, chairs, and umbrellas, adjacent to a brick building.
A hot tub with a metal ladder, surrounded by tiled walls, with a view of trees through a window.

13. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
United States
Jessica
$149 nightly
$171 total
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.
A large indoor swimming pool with multiple seating areas and large windows.
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.

14. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
Bristol
United States
Gabriela
$130 nightly
$150 total
Nov 1 - Nov 2
Total with taxes and fees
Home2 Suites by Hilton Bristol
A large, historic building with a covered porch and outdoor seating area.
A large, historic house with multiple chimneys, a covered porch, and lush greenery.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.
A sign for the Simsbury House, indicating it is a historic building from 1820.

15. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
United States
Kimberly
$197 nightly
$226 total
Nov 1 - Nov 2
Total with taxes and fees
Simsbury 1820 House
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.

16. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
United States
Carroll
$163 nightly
$188 total
Oct 18 - Oct 19
Total with taxes and fees
DoubleTree by Hilton Hotel Bristol, Connecticut
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.

17. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
United States
RAE
$144 nightly
$165 total
Nov 1 - Nov 2
Total with taxes and fees
Residence Inn by Marriott Hartford Avon
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.
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.

18. Gedney Farm

Gedney Farm
Great Barrington
United States
Terri
$190 nightly
$209 total
Nov 8 - Nov 9
Total with taxes and fees
Gedney Farm
A bedroom with two beds, a desk, a chair, a window with curtains, and a door with a glass panel.
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.
A motel sign with a 'VACANCY' notice, surrounded by well-maintained landscaping and a building with a red roof.

19. Hitching Post Country Motel

Hitching Post Country Motel
Cornwall Bridge
United States
Chris
$130 nightly
$150 total
Oct 11 - Oct 12
Total with taxes and fees
Hitching Post Country Motel
A conservatory with a glass ceiling, round tables, and chairs, and a brick wall with an exit sign.
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.
A spacious lobby with a grand staircase, multiple seating areas, and a reception desk.

20. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
United States
William
$212 nightly
$243 total
Oct 14 - Oct 15
Total with taxes and fees
Avon Old Farms Hotel
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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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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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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.
See properties

Top Winchester Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Great to be actually AT the airport."
Judith 1-night trip
Posted 5 hours ago
Sheraton Hartford Hotel at Bradley Airport
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

8/10 Good
"Bed was not very comfortable."
Laura 1-night trip
Posted 21 hours ago
Home2 Suites by Hilton Bristol
The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Wonderful stay! Beautiful property and pool, breakfast was delicious."
Jacqueline 1-night trip
Posted 21 hours ago
The Litchfield Inn
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent
"Nice place close to west Hartford. Staff was helpful."
Ronald 1-night trip
Posted 1 day ago
Homewood Suites by Hilton Hartford-Farmington
Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"Lovely comfortable place!!"
Susan 2-night trip
Posted 4 days ago
Simsbury 1820 House
Delamar West Hartford

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!"
Andrea 3-night trip
Posted 5 days ago
Delamar West Hartford
Interlaken Inn & Resort

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."
Suzanne 5-night trip
Posted 9 days ago
Interlaken Inn & Resort
Mayflower Inn & Spa, Auberge Collection

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."
Moshe 2-night trip
Posted 1 month ago
Mayflower Inn & Spa, Auberge Collection
Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

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."
Richard K. 5-night trip
Posted 1 month ago
Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

More cheap stays in Winchester

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
$86 nightly
$99 total
Oct 18 - Oct 19
Total with taxes and fees
Days Inn by Wyndham Torrington
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
$122 nightly
$140 total
Oct 25 - Oct 26
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
Hitching Post Country Motel

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT
$130 nightly
$150 total
Oct 11 - Oct 12
Total with taxes and fees
Hitching Post Country Motel
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT
$136 nightly
$156 total
Oct 11 - Oct 12
Total with taxes and fees
Americas Best Value Inn Torrington CT
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT
$149 nightly
$171 total
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
The Millerton Inn

The Millerton Inn

53 Main St Millerton NY
$279 nightly
$316 total
Oct 13 - Oct 14
Total with taxes and fees
8.4/10 Very Good! (46 reviews)
The Millerton Inn

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 $99 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.

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