Find hotels in Winchester, CT from $92

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May 15 - May 17
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May 22 - May 24

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Our top choices for Winchester hotels

Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
$105 nightly
The price is $121
May 15 - May 16
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (106 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
$140 nightly
The price is $155
May 18 - May 19
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (48 reviews)
"Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)"
United States
Maria
$161 nightly
The price is $180
May 20 - May 21
Total with taxes and fees
Wilder House Berkshires
Exterior

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (222 reviews)
"Great place for a quick family getaway!!"
United States
Rosemary
$135 nightly
The price is $155
May 25 - May 26
Total with taxes and fees
Home2 Suites by Hilton Bristol
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, (1,000 reviews)
"Rooms were fresh and clean, staff is very friendly and accommodating!"
United States
Amanda
$90 nightly
The price is $104
May 26 - May 27
Total with taxes and fees
Days Inn by Wyndham Torrington
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (63 reviews)
"This is a gem of a place. I have stayed at the abner many times and am delighted to say it is always a treat. The hotel is warm charming sparkling clean and perfectly located with shopping and dining just outside your doors. The rooms are comfortably appointed with all the extras of a posh stay . The breakfast is a must and don’t skip the frittata. Dinner is a cozy culinary experience with an ample menu to cover many tastes but dine exquisitely. If open do not miss out on the rooftop lounge...
United States
laura
$187 nightly
The price is $215
Jun 10 - Jun 11
Total with taxes and fees
The Abner Hotel
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (177 reviews)
"Great staff. "
United States
wesley
$150 nightly
The price is $173
May 26 - May 27
Total with taxes and fees
Blackberry River Inn
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (190 reviews)
"Staff was very rude.The owner was very rude.We'll never stay there again"
United States
Jeff
$80 nightly
The price is $92
May 26 - May 27
Total with taxes and fees
PLYMOUTH MOTOR LODGE
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (85 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
May 15 - May 16
Total with taxes and fees
Hitching Post Country Motel
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean room, friendly staff and quiet grounds."
United States
shaneice
$121 nightly
The price is $139
May 26 - May 27
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (26 reviews)
"Nice staff, great restaurant at the inn. Very cute town. "
United States
Valerie
$242 nightly
The price is $274
May 26 - May 27
Total with taxes and fees
The Millerton Inn
Lobby

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
"Jeannie at the front desk was helpful and very welcoming. Room was renovated since my last visit. "
United States
WAYNE
$89 nightly
The price is $99
May 24 - May 25
Total with taxes and fees
Elm Motel
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 reviews)
"Beautiful property and rooms."
United States
Kara
$175 nightly
The price is $192
May 17 - May 18
Total with taxes and fees
Gedney Farm
Front of property

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,001 reviews)
"Older buildings but clean and well maintained. Breakfast was good, staff was friendly."
United States
Linda
$154 nightly
The price is $177
May 18 - May 19
Total with taxes and fees
The Farmington Inn & Suites
Free daily continental breakfast

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (160 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
$212 nightly
The price is $243
May 15 - May 16
Total with taxes and fees
Cornwall Inn and Lodge
Exterior

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)
"Good coffee at breakfast. "
United States
Janet
$114 nightly
The price is $131
May 25 - May 26
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
Lobby

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.4 out of 10, Very Good, (975 reviews)
"Pool was cold and not a lot of great breakfast options other than that amazing stay "
United States
Ayanna
$114 nightly
The price is $131
May 25 - May 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
Library

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.0 out of 10, Wonderful, (991 reviews)
"Great stay! "
United States
Paige
$262 nightly
The price is $301
May 18 - May 19
Total with taxes and fees
The Litchfield Inn
Fountain

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,001 reviews)
"Great place to stay"
United States
Linda
$149 nightly
The price is $171
May 21 - May 22
Total with taxes and fees
Avon Old Farms Hotel
Front of property

Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
$299 nightly
The price is $332
Jun 1 - Jun 2
Total with taxes and fees
Manor House Inn
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

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2/10 Terrible
"Food was left in the fridge from the last guests. The room was so disgusting we went and bout our own blankets to sleep on top of the bed with. Everything about this place was disappointing and just gross!! For the extra few dollars, stay somewhere else!!!!"
Bryce 1-night trip
Posted 19 hours ago
Extended Stay America Suites Hartford Farmington

More cheap stays in Winchester

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
$90 nightly
The price is $104 total per night from May 26 to May 27
$104 total
May 26 - May 27
Total with taxes and fees
7.4/10 Good! (1,000 reviews)

Hotels in Winchester with star-rating

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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.

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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.

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