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Winchester Hotels

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Check prices for these dates

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

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Star rating

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. Iā€™d definitely return. Breakfast was great."
United States
Lawrence
The price is ā‚¬136
includes taxes & fees
20 Jul - 21 Jul
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
The price is ā‚¬106
includes taxes & fees
14 Jul - 15 Jul
Locust Tree Bed and Breakfast LLC
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
The price is ā‚¬169
includes taxes & fees
20 Jul - 21 Jul
Wilder House Berkshires
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
The price is ā‚¬150
includes taxes & fees
2 Aug - 3 Aug
Home2 Suites by Hilton Bristol
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
The price is ā‚¬157
includes taxes & fees
14 Jul - 15 Jul
Blackberry River Inn
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
The price is ā‚¬131
includes taxes & fees
12 Jul - 13 Jul
Hitching Post Country Motel
Double Room, Smoking

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
The price is ā‚¬90
includes taxes & fees
12 Jul - 13 Jul
PLYMOUTH MOTOR LODGE
Desk, free cots/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
The price is ā‚¬97
includes taxes & fees
2 Aug - 3 Aug
Days Inn by Wyndham Torrington
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 Iā€™m going to have this year. Great vibes, great staff and amazing food. 5/5 stars, would highly recommend staying."
United States
Mark
The price is ā‚¬236
includes taxes & fees
13 Jul - 14 Jul
The Abner Hotel
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
The price is ā‚¬145
includes taxes & fees
13 Jul - 14 Jul
The Farmington Inn & Suites
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
The price is ā‚¬174
includes taxes & fees
26 Jul - 27 Jul
Sunny Peace Homestay
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
The price is ā‚¬118
includes taxes & fees
12 Jul - 13 Jul
Homewood Suites by Hilton Hartford-Farmington
Exterior

Troutbeck

Troutbeck
5.0 star property
Amenia
10.0 out of 10, Exceptional, (2 reviews)
"Outstanding!!"
United States
Charles
The price is ā‚¬503
includes taxes & fees
15 Jul - 16 Jul
Troutbeck
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
The price is ā‚¬219
includes taxes & fees
16 Jul - 17 Jul
Cornwall Inn and Lodge
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
The price is ā‚¬126
includes taxes & fees
9 Aug - 10 Aug
Hampton Inn & Suites Hartford/Farmington
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
The price is ā‚¬248
includes taxes & fees
15 Jul - 16 Jul
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
The price is ā‚¬239
includes taxes & fees
2 Aug - 3 Aug
Sheraton Hartford Hotel at Bradley Airport
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
The price is ā‚¬115
includes taxes & fees
9 Aug - 10 Aug
Fairfield Inn & Suites by Marriott Plainville
Library

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,004 reviews)
"Staff were all very friendly and helpful. Breakfast was great!"
United States
Evan
The price is ā‚¬264
includes taxes & fees
14 Jul - 15 Jul
The Litchfield 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, (1,001 reviews)
"Room was clean and location in good area"
United States
Keith
The price is ā‚¬119
includes taxes & fees
2 Aug - 3 Aug
Extended Stay America 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

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 8 hours ago
The Litchfield Inn

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
The price is ā‚¬90 per night from 12 Jul to 13 Jul
ā‚¬90
12 Jul - 13 Jul
includes taxes & fees
7.8/10 Good! (198 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?
The Farmington Inn & Suites, located 20.6 mi (33.1 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Two other choices for your stay in the area are Avon Old Farms Hotel and Delamar West Hartford. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Lakefront Summer Stunner in New England Just 2 Hours From NYC: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private garden and a selection of games. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some hotels with pools in Winchester?
Avon Old Farms Hotel: Provides a sauna, a seasonal outdoor pool and buffet. Hampton Inn & Suites Hartford/Farmington and DoubleTree by Hilton Hotel Bristol, Connecticut are two additional hotels with an on-site pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester will definitely find plenty to explore and enjoy. In Winchester, there are 21 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I see while I'm in Winchester?
Favourite places to visit include The Marina at Highland Lake, Platt Hill State Park and Highland Lake. A couple of additional sights to add to your itinerary are Burr Pond State Park and Laurel Lanes. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the seasonal weather in Winchester?
The hottest months are usually July and August, with an average temperature of 20Ā°C, while the coldest months are January and February, with an average of -1Ā°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 15 cm of snowfall.

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