Default HTG hotel image

Find hotels in Winchester, CT from $92

Check prices for these dates

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Filter by

Star rating

Guest rating

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 building with a blue awning, a lobby entrance, and a well-maintained lawn with various plants.
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
Tyler
$82 nightly
$95 total
Nov 12 - Nov 13
Total with taxes and fees
Days Inn by Wyndham Torrington
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 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.

2. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Melanie
$173 nightly
$199 total
Oct 26 - Oct 27
Total with taxes and fees
Blackberry River Inn
A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.
Lobby
A gym with various exercise equipment, a mirror, and a blue wall.
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

Americas Best Value Inn Torrington CT
Torrington
United States
Tuty
$150 nightly
$172 total
Oct 25 - Oct 26
Total with taxes and fees
Americas Best Value Inn Torrington CT
A covered porch with white railings and rocking chairs.
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.

4. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Daniel
$105 nightly
$121 total
Oct 25 - Oct 26
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 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.
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.

5. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
United States
Dean
$181 nightly
$208 total
Nov 2 - Nov 3
Total with taxes and fees
Sunny Peace Homestay
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.

6. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
Granby
United States
Melanie
$140 nightly
$155 total
Oct 28 - Oct 29
Total with taxes and fees
Truman Gillet House Bed & Breakfast
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
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.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.

7. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
United States
Jennifer
$142 nightly
$163 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Hotel Bristol, Connecticut
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 large indoor swimming pool with multiple seating areas and large windows.

8. 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 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 spacious lobby with a patterned rug, a potted plant, and a television.
A well-lit room with a fireplace, two armchairs, a sofa, and a coffee table.

9. The Farmington Inn & Suites

The Farmington Inn & Suites
Farmington
United States
Kenneth
$140 nightly
$161 total
Nov 9 - Nov 10
Total with taxes and fees
The Farmington Inn & Suites
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 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.

10. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
United States
Enrique
$185 nightly
$213 total
Nov 4 - Nov 5
Total with taxes and fees
Simsbury 1820 House
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 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.

11. Avon Old Farms Hotel

Avon Old Farms Hotel
Avon
United States
Kristen
$186 nightly
$213 total
Oct 27 - Oct 28
Total with taxes and fees
Avon Old Farms Hotel
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 white building with a covered patio area, a brick chimney, and a garden with various plants and flowers.

12. The Litchfield Inn

The Litchfield Inn
Litchfield
United States
Jacqueline
$289 nightly
$332 total
Nov 15 - Nov 16
Total with taxes and fees
The Litchfield Inn
A hotel room with two beds, a nightstand with a lamp, and a wall-mounted phone.
A bathroom with a shower, toilet, and towel rack.
A heart-shaped bathtub with a single faucet and a drain.
A motel with a sign reading "Plymouth Motor Lodge".

13. PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
Terryville
United States
Melissa
$80 nightly
$92 total
Nov 23 - Nov 24
Total with taxes and fees
PLYMOUTH MOTOR LODGE
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 Marriott hotel with a red roof, a swimming pool, and a well-maintained lawn.

14. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
United States
Laura
$135 nightly
$155 total
Nov 19 - Nov 20
Total with taxes and fees
Residence Inn by Marriott Hartford Avon
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.

15. Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
Farmington
United States
Jessica
$144 nightly
$165 total
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
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.

16. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
Plainville
United States
Erin
$101 nightly
$116 total
Nov 8 - Nov 9
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
A hotel with multiple buildings, a parking lot, and a well-maintained lawn.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a lamp.
A modern kitchen with a central island, built-in cabinets, and a coffee station.
A modern lobby with a yellow sofa, marble table, and two armchairs.

17. Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
Farmington
United States
EDWARD
$152 nightly
$175 total
Oct 30 - Oct 31
Total with taxes and fees
Homewood Suites by Hilton Hartford-Farmington
A bedroom with two beds, a desk, a chair, a window with curtains, and a door with a glass panel.
A room with a mounted television, a chair, and a coat rack.
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.

18. Hitching Post Country Motel

Hitching Post Country Motel
Cornwall Bridge
United States
Chris
$130 nightly
$150 total
Oct 25 - Oct 26
Total with taxes and fees
Hitching Post Country Motel
A large, two-story house with a wrap-around porch, a central entrance, and a flag.
A dining area with a round table, chairs, a fireplace, and a variety of plants.
A modern house with a white exterior, two wooden doors, and a grey awning.
A swimming pool with lounge chairs and umbrellas, surrounded by trees.

19. Belden House & Mews

Belden House & Mews
Litchfield Historic District
United States
Anthony
$467 nightly
$537 total
Nov 17 - Nov 18
Total with taxes and fees
Belden House & Mews
A white two-story house with a front door, windows, and a chimney.
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 dining area with round tables set for two, a fireplace, and a mural on the wall.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

20. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
mary ellen
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
View all properties

Compare top hotels 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.

Days Inn by Wyndham Torrington

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

Blackberry River Inn

Norfolk
View
A hotel room with a large bed, bedside lamps, a desk with a chair, a mirror, and a coat rack.

Americas Best Value Inn Torrington CT

Torrington
View
A covered porch with white railings and rocking chairs.

Locust Tree Bed and Breakfast LLC

East Canaan
View
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

Sunny Peace Homestay

Harwinton
View
7.4
Good
1,001 reviews
9.4
Exceptional
243 reviews
5.6
831 reviews
8.8
Excellent
453 reviews
8.8
Excellent
18 reviews
$82 nightly
$95 total
Nov 12 - Nov 13
Total with taxes and fees
$173 nightly
$199 total
Oct 26 - Oct 27
Total with taxes and fees
$150 nightly
$172 total
Oct 25 - Oct 26
Total with taxes and fees
$105 nightly
$121 total
Oct 25 - Oct 26
Total with taxes and fees
$181 nightly
$208 total
Nov 2 - Nov 3
Total with taxes and fees
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winchester attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
See properties

Northwestern Connecticut Community College

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

Northwestern Connecticut Community College Library

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

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.
See properties

The Marina at Highland Lake

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

Rowley Fields

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

Ledgebrook Plaza

You can enjoy retail therapy at Ledgebrook Plaza during your stay in Winchester.
See properties

American Mural Project

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

Top Winchester Hotel Reviews

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"So quaint. Great little touches. They set out wine and charcuterie board and cookies every evening. Have a cappuccino machine in the lobby that is top class with all the fixings. Bed was so cozy. Wonderful place to stay. I loved it"
wendy 4-night trip
Posted 14 hours ago
The Farmington Inn & Suites
Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"Restaurant inside inn was comforting and had a great vibe."
Enrique 1-night trip
Posted 15 hours ago
Simsbury 1820 House
Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"great staff with customer service focus!"
Christopher 1-night trip
Posted 2 days ago
Delamar West Hartford
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Hotel was clean and modern. Hotel bar was fun and front desk was quick, friendly and efficient."
Jennifer 1-night trip
Posted 4 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut
The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Our room was very clean. They had an excellent breakfast with much to choose from."
Josephine 1-night trip
Posted 5 days ago
The Litchfield Inn
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

10/10 Excellent
"N"
Milo 2-night trip
Posted 5 days ago
Home2 Suites by Hilton Bristol
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent
"Very nice, comfortable stay. Would stay there again."
Erin 1-night trip
Posted 9 days ago
Fairfield Inn & Suites by Marriott Plainville
Troutbeck

Troutbeck

10/10 Excellent
"Absolutely stunning escape. Just go"
Ryan 1-night trip
Posted 1 month ago
Troutbeck
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 2 months ago
Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
$80 nightly
$92 total
Nov 23 - Nov 24
Total with taxes and fees
7.8/10 Good! (221 reviews)
PLYMOUTH MOTOR LODGE
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
$82 nightly
$95 total
Nov 12 - Nov 13
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
$109 nightly
$126 total
Nov 15 - Nov 16
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT
$144 nightly
$165 total
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT
$150 nightly
$172 total
Oct 25 - Oct 26
Total with taxes and fees
5.6/10 (831 reviews)
Americas Best Value Inn Torrington CT
The Millerton Inn

The Millerton Inn

53 Main St Millerton NY
$234 nightly
$265 total
Oct 25 - Oct 26
Total with taxes and fees
8.4/10 Very Good! (49 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 $92 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