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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 6 - May 7
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 3 - May 4
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (218 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
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (46 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
$180 nightly
The price is $201
May 4 - May 5
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, (1,001 reviews)
"Parking was great, staff very helpful, and the room was really clean. "
United States
Enrisa
$86 nightly
The price is $99
May 31 - Jun 1
Total with taxes and fees
Days Inn by Wyndham Torrington
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (83 reviews)
"Checkin was easy, room was clean and comfortable "
United States
Greg
$130 nightly
The price is $150
May 3 - May 4
Total with taxes and fees
Hitching Post Country Motel
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (188 reviews)
"Staff was very rude.The owner was very rude.We'll never stay there again"
United States
Jeff
$82 nightly
The price is $94
May 4 - May 5
Total with taxes and fees
PLYMOUTH MOTOR LODGE
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (175 reviews)
"Charming, quiet, clean very clean with a beautiful dining room for breakfast and very respectful service."
United States
Mara
$146 nightly
The price is $168
May 18 - May 19
Total with taxes and fees
Blackberry River Inn
Staircase

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
$137 nightly
The price is $158
May 4 - May 5
Total with taxes and fees
The Farmington Inn & Suites
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (19 reviews)
"Nice staff, great restaurant at the inn. Very cute town. "
United States
Valerie
$231 nightly
The price is $261
May 30 - May 31
Total with taxes and fees
The Millerton Inn
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, (1,003 reviews)
"Good coffee at breakfast. "
United States
Janet
$110 nightly
The price is $127
May 10 - May 11
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
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
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,001 reviews)
"Clean room, friendly staff and quiet grounds."
United States
shaneice
$122 nightly
The price is $141
May 25 - May 26
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, (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 5 - May 6
Total with taxes and fees
Cornwall Inn and Lodge
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (59 reviews)
"This hotel was absolutely beautiful, the staff was so helpful and attentive. We will definitely be back on our next stay in Litchfield. "
United States
Jessica
$311 nightly
The price is $358
Jun 1 - Jun 2
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, (789 reviews)
"Very pleasant check-in experience. Spacious room, comfortable beds, clean, easy parking."
United States
Laurel
$102 nightly
The price is $117
May 3 - May 4
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, (1,002 reviews)
"We liked this hotel"
United States
Katarzyna
$117 nightly
The price is $135
May 7 - May 8
Total with taxes and fees
Homewood Suites by Hilton Hartford-Farmington
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 14 - May 15
Total with taxes and fees
Gedney Farm
Fountain

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,002 reviews)
"Great place to stay"
United States
Linda
$145 nightly
The price is $167
May 12 - May 13
Total with taxes and fees
Avon Old Farms Hotel
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, (971 reviews)
"Pool was cold and not a lot of great breakfast options other than that amazing stay "
United States
Ayanna
$96 nightly
The price is $110
May 25 - May 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
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

Avon Old Farms Hotel

Avon Old Farms Hotel

8/10 Good
"Very interesting property; not "chain like". Room was comfortable, but bed was a bit off. did not have opportunity for breakfast."
Michael 2-night trip
Posted 8 hours ago
Avon Old Farms Hotel

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 May 4 to May 5
$94 total
May 4 - May 5
Total with taxes and fees
7.6/10 Good! (188 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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