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Mar 9 - Mar 10
Tomorrow
Mar 10 - Mar 11
This weekend
Mar 13 - Mar 15
Next weekend
Mar 20 - Mar 22

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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, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ￥16,567
￥19,052 total
includes taxes & fees
Mar 11 - Mar 12
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, (104 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is ￥22,089
￥24,519 total
includes taxes & fees
Mar 11 - Mar 12
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, (197 reviews)
"Clean room, great staff"
United States
Tamiya
The price is ￥19,880
￥22,862 total
includes taxes & fees
Mar 29 - Mar 30
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, (1,003 reviews)
"Staff was very friendly, room was clean. Overall great stay, thanks!"
United States
Nathaniel
The price is ￥15,289
￥17,582 total
includes taxes & fees
Mar 24 - Mar 25
Days Inn by Wyndham Torrington
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
The price is ￥24,416
￥27,620 total
includes taxes & fees
Mar 11 - Mar 12
The Millerton Inn
Interior

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,008 reviews)
"I love this hotel. Beds are so comfy, showers are hot with great water pressure, large bathrooms, nice amenities, friendly staff. "
United States
Ann
The price is ￥17,198
￥23,225 total
includes taxes & fees
Mar 11 - Mar 12
Avon Old Farms Hotel
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, (1,011 reviews)
"Great deal in the Hartford area. Large room, comfy bed and super nice people. Very convenient to I 95"
United States
Patricia
The price is ￥13,795
￥15,864 total
includes taxes & fees
Mar 26 - Mar 27
Extended Stay America Suites Hartford Farmington
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (183 reviews)
"Nice amount of space"
United States
Amanda
The price is ￥11,360
￥13,065 total
includes taxes & fees
Mar 12 - Mar 13
PLYMOUTH MOTOR LODGE
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,008 reviews)
"Very comfortable room, very nice staff. Breakfast was great. "
United States
Michael
The price is ￥19,278
￥22,169 total
includes taxes & fees
Mar 21 - Mar 22
Hampton Inn & Suites Hartford/Farmington
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 ￥30,416
￥33,976 total
includes taxes & fees
Mar 12 - Mar 13
Wilder House Berkshires
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (169 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ￥21,619
￥24,862 total
includes taxes & fees
Mar 23 - Mar 24
Blackberry River Inn
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
"Love the inn"
United States
Donna
The price is ￥19,657
￥25,329 total
includes taxes & fees
Mar 16 - Mar 17
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, (942 reviews)
"Rooms were clean and staff was courteous. "
United States
Keith
The price is ￥16,567
￥19,052 total
includes taxes & fees
Apr 3 - Apr 4
Fairfield Inn & Suites by Marriott Plainville
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (53 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 ￥34,286
￥39,430 total
includes taxes & fees
Mar 30 - Mar 31
The Abner Hotel
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)
"Basic accommodation that was clean and easy."
United States
Elizabeth
The price is ￥20,511
￥23,588 total
includes taxes & fees
Mar 11 - Mar 12
Hitching Post Country Motel
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 ￥33,386
￥38,394 total
includes taxes & fees
Mar 11 - Mar 12
Cornwall Inn and Lodge
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (285 reviews)
"Great"
United States
Jorge
The price is ￥28,258
￥32,497 total
includes taxes & fees
Mar 11 - Mar 12
Interlaken Inn & Resort
Reception

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,003 reviews)
"Lovely staff, beautiful room, comfy bed, delicious fresh breakfast. "
United States
Debra
The price is ￥25,087
￥31,572 total
includes taxes & fees
Mar 11 - Mar 12
Simsbury 1820 House
Exterior

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,006 reviews)
"I love this Wonderful Location and the breakfast is astounding!"
United States
Mark
The price is ￥33,466
￥38,486 total
includes taxes & fees
Apr 4 - Apr 5
Sheraton Hartford Hotel at Bradley Airport
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, (1,004 reviews)
"Very courteous staff. Room was clean and spotless."
United States
Richard
The price is ￥22,398
￥25,758 total
includes taxes & fees
Mar 20 - Mar 21
Homewood Suites by Hilton 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

Platt Hill State Park

You can take time to visit Platt Hill State Park during your travels to Winchester.
See properties

Top Winchester Hotel Reviews

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Beautiful property and complimentary breakfast on the go made our stay memorable, looking to coming back in the future."
Nabonita 1-night trip
Posted 6 hours ago
Avon Old Farms Hotel

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
The price is ￥11,360 per night from Mar 12 to Mar 13
￥11,360
￥13,065 total
Mar 12 - Mar 13
includes taxes & fees

Frequently asked questions

What's the best place for a stay in Winchester?
Sheraton Hartford Hotel at Bradley Airport, located 21.9 mi (35.2 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Extended Stay America Suites Hartford Farmington and Hampton Inn & Suites Hartford/Farmington. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental in Winchester?
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This vacation home rental outside of Winchester offers a fireplace, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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! You'll find that most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.
What are some hotels with pools in Winchester?
Hampton Inn & Suites Hartford/Farmington: Offers daily, an indoor pool, and complimentary wired internet access. Avon Old Farms Hotel and Simsbury 1820 House are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester are sure to find plenty to explore and enjoy. In Winchester, there are 17 hotels and other accommodations to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Favorite places to visit include Highland Lake, Burr Pond State Park, and The Marina at Highland Lake. A couple of additional sights to add to your agenda are Platt Hill State Park and Winchester Historical Society. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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