Winchester Hotels

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Check prices for these dates

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2 Apr - 3 Apr
Tomorrow
3 Apr - 4 Apr
This weekend
3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

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Our top choices for Winchester hotels

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
The price is €134
includes taxes & fees
3 Apr - 4 Apr
Truman Gillet House Bed & Breakfast
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
The price is €104
includes taxes & fees
4 Apr - 5 Apr
Locust Tree Bed and Breakfast LLC
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (204 reviews)
"Great place good people decent breakfast great room service "
United States
JULES
The price is €136
includes taxes & fees
23 Apr - 24 Apr
Home2 Suites by Hilton Bristol
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is €155
includes taxes & fees
7 Apr - 8 Apr
Wilder House Berkshires
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, (1,000 reviews)
"Staff was very attentive to my needs. I required support on two occasions during the length of my stay and they took care of the problem immediately. "
United States
Michele
The price is €83
includes taxes & fees
8 Apr - 9 Apr
Days Inn by Wyndham Torrington
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (184 reviews)
"Staff was very rude.The owner was very rude.We'll never stay there again"
United States
Jeff
The price is €84
includes taxes & fees
3 May - 4 May
PLYMOUTH MOTOR LODGE
Lobby

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (954 reviews)
"Average clean rooms, pool small, pizza Resterant good. Staff great at hotel and Resterant. "
United States
Kellie
The price is €104
includes taxes & fees
17 Apr - 18 Apr
Fairfield Inn & Suites by Marriott Plainville
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
The price is €154
includes taxes & fees
14 Apr - 15 Apr
Blackberry River Inn
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,000 reviews)
"Nice clean hotel "
United States
Tiffany
The price is €121
includes taxes & fees
10 Apr - 11 Apr
Hampton Inn & 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
The price is €141
includes taxes & fees
5 Apr - 6 Apr
The Farmington Inn & Suites
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, (1,002 reviews)
"Feels like home ! Great experience! "
United States
Yong
The price is €108
includes taxes & fees
12 Apr - 13 Apr
Extended Stay America Suites Hartford Farmington
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
The price is €129
includes taxes & fees
3 Apr - 4 Apr
Hitching Post Country Motel
Executive lounge

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,000 reviews)
"Stay was great! "
United States
Teresa
The price is €267
includes taxes & fees
5 Apr - 6 Apr
Sheraton Hartford Hotel at Bradley Airport
Free daily continental breakfast

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (157 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
The price is €210
includes taxes & fees
3 Apr - 4 Apr
Cornwall Inn and Lodge
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (291 reviews)
"Overall great amenities and great price"
United States
Stacie
The price is €178
includes taxes & fees
6 Apr - 7 Apr
Interlaken Inn & Resort
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
The price is €156
includes taxes & fees
5 Apr - 6 Apr
Gedney Farm
Reception

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,000 reviews)
"The stay was great, very accommodating staff, quaint rooms and lounge area!"
United States
Cathy
The price is €173
includes taxes & fees
4 Apr - 5 Apr
Simsbury 1820 House
Interior

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1,000 reviews)
"Beautiful property and complimentary breakfast on the go made our stay memorable, looking to coming back in the future."
United States
Nabonita
The price is €157
includes taxes & fees
4 Apr - 5 Apr
Avon Old Farms Hotel
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (58 reviews)
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
The price is €305
includes taxes & fees
27 Apr - 28 Apr
The Abner Hotel
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very good, (18 reviews)
"Perfect "
United States
Zhigang
The price is €245
includes taxes & fees
4 Apr - 5 Apr
The Millerton 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

Northwestern Connecticut Community College

Explore the campus of Northwestern Connecticut Community College during your stay in Winchester.
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Top Winchester Hotel Reviews

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

10/10 Excellent
"Beautiful spot! Very clean ❤️"
Peggy 1-night trip
Posted 6 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
The price is €83 per night from 8 Apr to 9 Apr
€83
8 Apr - 9 Apr
includes taxes & fees
7.4/10 Good! (1,000 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 Sheraton Hartford Hotel at Bradley Airport and Extended Stay America Suites Hartford Farmington. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This holiday home rental outside of Winchester offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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: Offers a sauna, a seasonal outdoor pool and buffet. Hampton Inn & Suites Hartford/Farmington and Fairfield Inn & Suites by Marriott Plainville 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 16 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 Highland Lake, American Mural Project and Burr Pond State Park. A couple of additional sights to add to your itinerary are The Marina at Highland Lake and Winchester Historical Society. 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 20°C, while the coldest months are January and February, with an average of -1°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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