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Check prices for these dates

Tonight
15 Feb - 16 Feb
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16 Feb - 17 Feb
Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar

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Our top choices for Winchester hotels

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)
  • cleanliness
    Modern Torrington motel offers easy access to local attractions and outdoor activities.
"Very respectable staff and clean environment "
United States
Hannah
The price is NZ$160
includes taxes & fees
17 Feb - 18 Feb
Days Inn by Wyndham Torrington
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)
  • cleanliness
    Experience the charming Locust Tree B&B in East Canaan with free breakfast.
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is NZ$200
includes taxes & fees
16 Feb - 17 Feb
Locust Tree Bed and Breakfast LLC
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very good, (13 reviews)
  • cleanliness
    Escape to a Mediterranean culinary gem in historic Millerton with complimentary perks.
"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 NZ$302
includes taxes & fees
16 Feb - 17 Feb
The Millerton Inn
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (189 reviews)
  • cleanliness
    Comfortable suite-style rooms in Bristol with free breakfast and a relaxing spa pool.
"Clean room, great staff"
United States
Tamiya
The price is NZ$248
includes taxes & fees
22 Feb - 23 Feb
Home2 Suites by Hilton Bristol
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)
  • cleanliness
    Historic Connecticut B&B surrounded by scenic trails and nature attractions.
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is NZ$257
includes taxes & fees
16 Feb - 17 Feb
Truman Gillet House Bed & Breakfast
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Tranquil retreat with health club and complimentary breakfast in Farmington.
"This place is like a warm hug from your favorite auntie. "
United States
kieran
The price is NZ$238
includes taxes & fees
28 Feb - 1 Mar
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)
  • cleanliness
    Stay at a tranquil hotel with free breakfast and parking in Farmington.
"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$144
includes taxes & fees
16 Feb - 17 Feb
Extended Stay America Suites Hartford Farmington
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
  • cleanliness
    Serene New England escape offers tranquil country setting with seasonal pool.
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NZ$291
includes taxes & fees
23 Feb - 24 Feb
Blackberry River Inn
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
  • cleanliness
    Unwind in the Berkshires at this charming B&B with free weekend breakfast.
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is NZ$332
includes taxes & fees
18 Feb - 19 Feb
Wilder House Berkshires
Lobby

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (933 reviews)
  • cleanliness
    Quiet haven near Crescent Lake with indoor pool and 24-hour fitness centre.
"Rooms were clean and staff was courteous. "
United States
Keith
The price is NZ$204
includes taxes & fees
20 Feb - 21 Feb
Fairfield Inn & Suites by Marriott Plainville
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Experience New England comfort and amenities just 15 minutes from Hartford.
"Very comfortable room, very nice staff. Breakfast was great. "
United States
Michael
The price is NZ$233
includes taxes & fees
28 Feb - 1 Mar
Hampton Inn & Suites Hartford/Farmington
Interior

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1,001 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 NZ$236
includes taxes & fees
11 Mar - 12 Mar
Avon Old Farms Hotel
Interior

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (180 reviews)
  • cleanliness
    Relax in modern comfort just minutes from Terryville's top attractions.
"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$142
includes taxes & fees
23 Feb - 24 Feb
PLYMOUTH MOTOR LODGE
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (81 reviews)
  • cleanliness
    Cosy Connecticut motel near hiking trails offers a gateway to outdoor adventures.
"Basic accommodation that was clean and easy."
United States
Elizabeth
The price is NZ$248
includes taxes & fees
16 Feb - 17 Feb
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)
  • cleanliness
    Enjoy a refreshing country stay with a pool at this charming Cornwall Bridge inn.
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
The price is NZ$403
includes taxes & fees
16 Feb - 17 Feb
Cornwall Inn and Lodge
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (51 reviews)
  • cleanliness
    Elevated modern hotel with a rooftop terrace near Litchfield Town Green.
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
The Abner Hotel
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, (1,004 reviews)
  • cleanliness
    Experience direct airport access with convenient 24-hour fitness at this Windsor Locks hotel.
"I love this Wonderful Location and the breakfast is astounding!"
United States
Mark
The price is NZ$436
includes taxes & fees
28 Feb - 1 Mar
Sheraton Hartford Hotel at Bradley Airport
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (280 reviews)
  • cleanliness
    Lakeside resort with golf course access and seasonal outdoor pool offers a serene escape.
"Great"
United States
Jorge
The price is NZ$314
includes taxes & fees
16 Feb - 17 Feb
Interlaken Inn & Resort
Lobby

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
  • cleanliness
    Comfortable motel near Big E with convenient parking and 24/7 service.
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is NZ$183
includes taxes & fees
24 Feb - 25 Feb
Elm Motel
Reception

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Experience history and comfort at this restored 1820 inn with two lounges.
"Lovely staff, beautiful room, comfy bed, delicious fresh breakfast. "
United States
Debra
The price is NZ$331
includes taxes & fees
16 Feb - 17 Feb
Simsbury 1820 House
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

The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.
See properties

Top Winchester Hotel Reviews

Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"Staff was great, room was cozy. Nice quiet sitting area to relax and have a cup of coffee."
John 1-night trip
Posted 2 days ago
Simsbury 1820 House

More cheap accommodation in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
The price is NZ$142 per night from 23 Feb to 24 Feb
NZ$142
23 Feb - 24 Feb
includes taxes & fees
7.6/10 Good! (180 reviews)

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 The Farmington Inn & Suites 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?
Hampton Inn & Suites Hartford/Farmington: Features daily, an indoor pool and complimentary high-speed (wired) Internet access. Simsbury 1820 House and Avon Old Farms Hotel 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 Winchester Historical Society and Platt Hill State Park. 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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