Find hotels in Winchester, CT from $86

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Our top choices for Winchester hotels

Premium bedding, down comforters, Select Comfort beds, in-room safe
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (783)
"Very pleasant check-in experience. Spacious room, comfortable beds, clean, easy parking."
United States
Laurel
$87 nightly
The price is $100
Feb 1 - Feb 2
Total with taxes and fees
Americas Best Value Inn Torrington CT
Desk, free cribs/infant beds, rollaway beds, free WiFi
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1000)
"Clean comfortable room,great parking and local shopping "
United States
Julie
$91 nightly
The price is $105
Jan 22 - Jan 23
Total with taxes and fees
Days Inn by Wyndham Torrington
Indoor spa tub
Simsbury Inn

Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (283)
"The personnel was very helpful & accomodating, both at the front desk & upstairs restaurant. I appreciated that they set out two rooms as adjoining even before I asked. "
United States
Sara
$258 nightly
The price is $297
Jan 24 - Jan 25
Total with taxes and fees
Simsbury Inn
Lobby
Elm Motel

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
$89 nightly
The price is $99
Jan 23 - Jan 24
Total with taxes and fees
Elm Motel
Lobby
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
2.5 star property
Plainville
8.6 out of 10, Excellent, (920)
"The room was very clean, and the check-in staff was very courteous."
United States
Kristin
$105 nightly
The price is $121
Jan 29 - Jan 30
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
Reception
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1000)
"Excellent stay "
United States
Suzanne
$174 nightly
The price is $200
Jan 11 - Jan 12
Total with taxes and fees
Simsbury 1820 House
Desk, iron/ironing board, free WiFi, bed sheets
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very Good, (1000)
"it’s just a very moderate place to stay"
United States
suzanne
$80 nightly
The price is $92
Feb 2 - Feb 3
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
Free WiFi, bed sheets
Hitching Post Country Motel

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (81)
"Basic accommodation that was clean and easy."
United States
Elizabeth
$130 nightly
The price is $150
Jan 9 - Jan 10
Total with taxes and fees
Hitching Post Country Motel
Terrace/patio
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (179)
"Clean room, great staff"
United States
Tamiya
$130 nightly
The price is $150
Jan 25 - Jan 26
Total with taxes and fees
Home2 Suites by Hilton Bristol
Free daily continental breakfast
Cornwall Inn and Lodge

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
$212 nightly
The price is $243
Jan 9 - Jan 10
Total with taxes and fees
Cornwall Inn and Lodge
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (275)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
$177 nightly
The price is $204
Feb 8 - Feb 9
Total with taxes and fees
Interlaken Inn & Resort
Breakfast, lunch, dinner served; American cuisine
The Old Inn On The Green

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
$336 nightly
The price is $368
Jan 11 - Jan 12
Total with taxes and fees
The Old Inn On The Green
Property entrance
Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (102)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
$140 nightly
The price is $155
Jan 9 - Jan 10
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Interior
PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (178)
"Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50"
United States
David
$74 nightly
The price is $86
Jan 10 - Jan 11
Total with taxes and fees
PLYMOUTH MOTOR LODGE
Front of property
Gedney Farm

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (134)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
$206 nightly
The price is $226
Jan 11 - Jan 12
Total with taxes and fees
Gedney Farm
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi
The White Hart

The White Hart

The White Hart
4.0 star property
Salisbury
9.6 out of 10, Exceptional, (145)
"Amazing stay. Incredible staff, attention to detail. Beyond expectations "
United States
Jeanette
$235 nightly
The price is $271
Jan 12 - Jan 13
Total with taxes and fees
The White Hart
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds
9 Academy

9 Academy

9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
$494 nightly
The price is $568
Jan 12 - Jan 13
Total with taxes and fees
9 Academy
Exterior
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very Good, (1000)
"Everything from reservation to check-in. Room cleanliness and dining room selections were excellent."
United States
Ken
$122 nightly
The price is $141
Jan 11 - Jan 12
Total with taxes and fees
Homewood Suites by Hilton Hartford-Farmington
Staircase
The Farmington Inn & Suites

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1001)
"Love the inn"
United States
Donna
$105 nightly
The price is $121
Jan 11 - Jan 12
Total with taxes and fees
The Farmington Inn & Suites
Exterior
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1000)
"It was great, clean, friendly!!"
United States
Stacey
$122 nightly
The price is $141
Jan 31 - Feb 1
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.
See properties

Northwestern Connecticut Community College

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

Top Winchester Hotel Reviews

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Custom made eggs Very tasty"
DELIA 1-night trip
Posted 3 days ago
The Litchfield Inn

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
$74 nightly
The price is $86 total per night from Jan 10 to Jan 11
$86 total
Jan 10 - Jan 11
Total with taxes and fees
7.6/10 Good! (178 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 can I save on a Winchester hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winchester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $86 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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