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Find hotels in Winchester, CT from $94

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Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

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Our top choices for Winchester hotels

Breakfast included
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (112 reviews)
"Very nice and comfortable place to stay. I’d definitely return. Breakfast was great."
United States
Lawrence
$140 nightly
The price is $155
Jul 13 - Jul 14
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (430 reviews)
"Below average B&B"
United States
Larry
$105 nightly
The price is $121
Jul 12 - Jul 13
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Double Room, Smoking | Iron/ironing board, free WiFi, bed sheets

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (198 reviews)
"Everything was nice! I'd stay here again!"
United States
SEMORA
$82 nightly
The price is $94
Jul 13 - Jul 14
Total with taxes and fees
PLYMOUTH MOTOR LODGE
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
$193 nightly
The price is $215
Jul 19 - Jul 20
Total with taxes and fees
Wilder House Berkshires
Desk, free cribs/infant beds, rollaway beds, free WiFi

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,005 reviews)
"Good clean place to stay "
United States
keith
$96 nightly
The price is $110
Aug 2 - Aug 3
Total with taxes and fees
Days Inn by Wyndham Torrington
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (191 reviews)
"beautiful inn"
United States
Maura
$156 nightly
The price is $179
Jul 23 - Jul 24
Total with taxes and fees
Blackberry River Inn
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (239 reviews)
"Overall good stay"
United States
Susan
$149 nightly
The price is $172
Aug 2 - Aug 3
Total with taxes and fees
Home2 Suites by Hilton Bristol
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
"Staff was very friendly accommodating and helpful"
United States
alecia
$144 nightly
The price is $166
Jul 12 - Jul 13
Total with taxes and fees
The Farmington Inn & Suites
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (94 reviews)
"A little dated but clean. A room for the night for when I race at lime rock"
United States
William
$130 nightly
The price is $150
Jul 11 - Jul 12
Total with taxes and fees
Hitching Post Country Motel
Garden

Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (8 reviews)
"Angela is very respectful and generous to her guests."
United States
Jean
$187 nightly
The price is $215
Jul 19 - Jul 20
Total with taxes and fees
Sunny Peace Homestay
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.6 out of 10, Exceptional, (74 reviews)
"I actual live in town and always wanted to stay here with my wife and dine here. Super clean room, very chill atmosphere, well decorated and most importantly, a comfortable bed. The staff was incredible and very attentive. But the real shinning star was the Courthouse restaurant, probably one of the best meals I’m going to have this year. Great vibes, great staff and amazing food. 5/5 stars, would highly recommend staying."
United States
Mark
$261 nightly
The price is $301
Aug 2 - Aug 3
Total with taxes and fees
The Abner Hotel
Premium bedding, down comforters, Select Comfort beds, in-room safe

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (800 reviews)
"Great hotel. Good service."
United States
Anisha
$127 nightly
The price is $147
Aug 1 - Aug 2
Total with taxes and fees
Americas Best Value Inn Torrington CT
Exterior

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very Good, (1,016 reviews)
"the staff was helpful and very friendly and the property and the breakfast were great! we enjoyed our stay and will be back."
United States
Kelly
$130 nightly
The price is $150
Jul 19 - Jul 20
Total with taxes and fees
Homewood Suites by Hilton Hartford-Farmington
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,011 reviews)
"Great stay and would definitely be back to stay again"
United States
Mary Melissa
$123 nightly
The price is $141
Aug 9 - Aug 10
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
Free daily continental breakfast

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (166 reviews)
"A charming stopover on our weekend travels. Small, quiet and lovely. Nice conversation with the host over breakfast too."
United States
Janice
$212 nightly
The price is $243
Jul 19 - Jul 20
Total with taxes and fees
Cornwall Inn and Lodge
Exterior

Troutbeck

Troutbeck
5.0 star property
Amenia
10.0 out of 10, Exceptional, (2 reviews)
"Outstanding!!"
United States
Charles
$507 nightly
The price is $574
Jul 15 - Jul 16
Total with taxes and fees
Troutbeck
Desk, iron/ironing board, free WiFi, bed sheets

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very Good, (1,001 reviews)
"Room was clean and location in good area"
United States
Keith
$118 nightly
The price is $135
Aug 2 - Aug 3
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
Lobby lounge

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (999 reviews)
"Great Service and food was decent."
United States
Sy A
$114 nightly
The price is $131
Aug 2 - Aug 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.6 out of 10, Excellent, (31 reviews)
"We had a beautiful experience, staff was very accommodating."
United States
Bernadette
$279 nightly
The price is $316
Jul 12 - Jul 13
Total with taxes and fees
The Millerton Inn
Bar (on property)

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location right outside the airport. Food reasonably priced and delicious."
United States
Stacy
$237 nightly
The price is $273
Aug 2 - Aug 3
Total with taxes and fees
Sheraton Hartford Hotel at Bradley Airport
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

Top Winchester Hotel Reviews

The Litchfield Inn

The Litchfield Inn

8/10 Good
"Ok beautiful hotel but somewhat strange. You are not close to town yet there is no bar area or restaurant in the whole place? Exceptional decorated lobby and many areas to get together but without food/bar just not used by anyone in when we were there. You felt like you were in a quiet spa not a hotel. They do serve an excellent breakfast though."
Jean Shannon 1-night trip
Posted 9 hours ago
The Litchfield Inn

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
$82 nightly
The price is $94 total per night from Jul 13 to Jul 14
$94 total
Jul 13 - Jul 14
Total with taxes and fees
7.8/10 Good! (198 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 $94 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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