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28 Feb - 1 Mar
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1 Mar - 2 Mar
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6 Mar - 8 Mar
In two weeks
13 Mar - 15 Mar

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Our top choices for Winchester hotels

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 NZ$249
includes taxes & fees
1 Mar - 2 Mar
Hitching Post Country Motel
Premium bedding, down duvets, 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, (785 reviews)
"Very pleasant check-in experience. Spacious room, comfortable beds, clean, easy parking."
United States
Laurel
The price is NZ$212
includes taxes & fees
4 Mar - 5 Mar
Americas Best Value Inn Torrington CT
Indoor spa tub

Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (288 reviews)
"Great stay, location, and service!!"
United States
Joey
The price is NZ$490
includes taxes & fees
1 Mar - 2 Mar
Simsbury Inn
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 NZ$406
includes taxes & fees
3 Mar - 4 Mar
Cornwall Inn and Lodge
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (194 reviews)
"Clean room, great staff"
United States
Tamiya
The price is NZ$255
includes taxes & fees
8 Mar - 9 Mar
Home2 Suites by Hilton Bristol
Reception

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,000 reviews)
"Lovely staff, beautiful room, comfy bed, delicious fresh breakfast. "
United States
Debra
The price is NZ$313
includes taxes & fees
3 Mar - 4 Mar
Simsbury 1820 House
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 friendly, room was clean. Overall great stay, thanks!"
United States
Nathaniel
The price is NZ$178
includes taxes & fees
8 Mar - 9 Mar
Days Inn by Wyndham Torrington
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (135 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is NZ$339
includes taxes & fees
8 Mar - 9 Mar
Gedney Farm
Lobby

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (941 reviews)
"Rooms were clean and staff was courteous. "
United States
Keith
The price is NZ$194
includes taxes & fees
20 Mar - 21 Mar
Fairfield Inn & Suites by Marriott Plainville
Breakfast, lunch, dinner served; American cuisine

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is NZ$614
includes taxes & fees
18 Mar - 19 Mar
The Old Inn On The Green
Terrace/patio

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1,000 reviews)
"clean room, quiet overnight, great hot tub "
United States
MELANIE
The price is NZ$291
includes taxes & fees
8 Mar - 9 Mar
DoubleTree by Hilton Hotel Bristol, Connecticut
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)
"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 NZ$159
includes taxes & fees
26 Mar - 27 Mar
Extended Stay America Suites Hartford Farmington
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (182 reviews)
"Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50"
United States
David
The price is NZ$141
includes taxes & fees
7 Mar - 8 Mar
PLYMOUTH MOTOR LODGE
Terrace/patio

Troutbeck

Troutbeck
5.0 star property
Amenia
The price is NZ$1,073
includes taxes & fees
8 Mar - 9 Mar
Troutbeck
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (284 reviews)
"Great"
United States
Jorge
The price is NZ$343
includes taxes & fees
3 Mar - 4 Mar
Interlaken Inn & Resort
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 NZ$259
includes taxes & fees
1 Mar - 2 Mar
Truman Gillet House Bed & Breakfast
BBQ/picnic Area

Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (425 reviews)
"Love the hotel "
United States
Carmen
The price is NZ$259
includes taxes & fees
8 Mar - 9 Mar
Residence Inn by Marriott Hartford Avon
Lunch and dinner served

Delamar West Hartford

Delamar West Hartford
4.0 star property
West Hartford
9.8 out of 10, Exceptional, (1,000 reviews)
"Clean room, great staff and overall warm atmosphere."
United States
Gavrosh
The price is NZ$598
includes taxes & fees
8 Mar - 9 Mar
Delamar West Hartford
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 NZ$330
includes taxes & fees
1 Mar - 2 Mar
Wilder House Berkshires
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)
"Very comfortable room, very nice staff. Breakfast was great. "
United States
Michael
The price is NZ$234
includes taxes & fees
21 Mar - 22 Mar
Hampton Inn & 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.
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The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.
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Top Winchester Hotel Reviews

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Clean "
Jennifer 1-night trip
Posted 4 days ago
Hampton Inn & Suites Hartford/Farmington

More cheap accommodation in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
The price is NZ$141 per night from 7 Mar to 8 Mar
NZ$141
7 Mar - 8 Mar
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 traveller data. Two other choices for your stay in 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 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?
Hampton Inn & Suites Hartford/Farmington: Features daily, an indoor pool and complimentary high-speed (wired) Internet access. Avon Old Farms Hotel and Simsbury 1820 House 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 17 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, Highland Lake and Burr Pond State Park. A couple of additional sights to add to your itinerary are Platt Hill State Park and Ledgebrook Plaza. 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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