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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, (416 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Apr 20 - Apr 21
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, (105 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
$140 nightly
The price is $155
Apr 22 - Apr 23
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, (213 reviews)
"Great place good people decent breakfast great room service "
United States
JULES
$134 nightly
The price is $154
Apr 30 - May 1
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, (44 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
$150 nightly
The price is $168
Apr 30 - May 1
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, (1,003 reviews)
"Staff was very friendly, room was clean. Overall great stay, thanks!"
United States
Nathaniel
$88 nightly
The price is $101
Apr 26 - Apr 27
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, (173 reviews)
"Best host (Lucas) makes all the difference! Great views and delicious breakfasts. "
United States
diane
$154 nightly
The price is $177
Apr 29 - Apr 30
Total with taxes and fees
Blackberry River Inn
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (18 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
$237 nightly
The price is $268
Apr 26 - Apr 27
Total with taxes and fees
The Millerton Inn
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,005 reviews)
"Nice clean hotel "
United States
Tiffany
$136 nightly
The price is $157
May 4 - May 5
Total with taxes and fees
Hampton Inn & Suites Hartford/Farmington
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)
"Feels like home ! Great experience! "
United States
Yong
$103 nightly
The price is $118
Apr 27 - Apr 28
Total with taxes and fees
Extended Stay America Suites Hartford Farmington
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
"Lovely stay!"
United States
Ilana
$137 nightly
The price is $158
May 5 - May 6
Total with taxes and fees
The Farmington Inn & Suites
Lobby

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (960 reviews)
"Average clean rooms, pool small, pizza Resterant good. Staff great at hotel and Resterant. "
United States
Kellie
$105 nightly
The price is $121
Apr 23 - Apr 24
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (186 reviews)
"Staff was very rude.The owner was very rude.We'll never stay there again"
United States
Jeff
$78 nightly
The price is $90
May 10 - May 11
Total with taxes and fees
PLYMOUTH MOTOR LODGE
Porch

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection
5.0 star property
Washington
9.4 out of 10, Exceptional, (59 reviews)
"Clean room "
United States
Casey
$664 nightly
The price is $763
Apr 20 - Apr 21
Total with taxes and fees
Mayflower Inn & Spa, Auberge Collection
Free daily continental breakfast

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (158 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
$212 nightly
The price is $243
Apr 20 - Apr 21
Total with taxes and fees
Cornwall Inn and Lodge
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
Apr 20 - Apr 21
Total with taxes and fees
Gedney Farm
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
Apr 20 - Apr 21
Total with taxes and fees
Hitching Post Country Motel
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (292 reviews)
"Overall great amenities and great price"
United States
Stacie
$233 nightly
The price is $268
May 13 - May 14
Total with taxes and fees
Interlaken Inn & Resort
Interior

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,004 reviews)
"Beautiful property and complimentary breakfast on the go made our stay memorable, looking to coming back in the future."
United States
Nabonita
$149 nightly
The price is $171
Apr 20 - Apr 21
Total with taxes and fees
Avon Old Farms Hotel
Library

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.0 out of 10, Wonderful, (981 reviews)
"Our stay was increidble!"
United States
Deborah
$248 nightly
The price is $285
Apr 20 - Apr 21
Total with taxes and fees
The Litchfield Inn
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

9 Academy
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (11 reviews)
"Extremely clean and the rooms are beautifully decorated with warm minimal decor. We will definitely be back!"
United States
Gina
$446 nightly
The price is $513
Apr 20 - Apr 21
Total with taxes and fees
9 Academy
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

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2/10 Terrible
"The bed coverings were stained, the pillows were very lumpy, the bathroom mat had brown stains on it. I cancelled my reservation and expect a refund. There was a strange man hanging around the front. There was a family “ living “ in the back. I don’t recommend this hotel at all!!"
Karen 2-night trip
Posted 13 hours ago
Days Inn by Wyndham Torrington

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
$78 nightly
The price is $90 total per night from May 10 to May 11
$90 total
May 10 - May 11
Total with taxes and fees
7.6/10 Good! (186 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 $90 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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