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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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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

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1005)
"Clean comfortable room,great parking and local shopping "
United States
Julie
The price is AU$160
includes taxes & fees
28 Dec - 29 Dec
Days Inn by Wyndham Torrington
Lobby
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
2.5 star property
Plainville
8.6 out of 10, Excellent, (912)
"Great place stayed several times."
United States
Marlene D
The price is AU$165
includes taxes & fees
2 Jan - 3 Jan 2026
Fairfield Inn & Suites by Marriott Plainville
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AU$180
includes taxes & fees
25 Dec - 26 Dec
Locust Tree Bed and Breakfast LLC
Staircase
The Farmington Inn & Suites

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1002)
"Love the inn"
United States
Donna
The price is AU$172
includes taxes & fees
4 Jan - 5 Jan 2026
The Farmington Inn & Suites
Exterior
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1000)
"Professional very clean and good breakfast "
United States
Piotr
The price is AU$210
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Inn & Suites Hartford/Farmington
Seasonal outdoor pool, pool umbrellas, pool loungers
Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (412)
"Good hotel but expensive "
United States
Christopher
The price is AU$203
includes taxes & fees
30 Dec - 31 Dec
Residence Inn by Marriott Hartford Avon
Interior
Avon Old Farms Hotel

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very good, (1000)
"Very nice place to stay"
United States
Alvero
The price is AU$202
includes taxes & fees
28 Dec - 29 Dec
Avon Old Farms Hotel
BBQ/picnic Area
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very good, (1000)
"The young woman who greeted my daughter and I was very sweet and kind. The room was clean and the beds very comfortable. Would definitely stay here again!"
United States
Lisa
The price is AU$210
includes taxes & fees
1 Jan - 2 Jan 2026
Homewood Suites by Hilton Hartford-Farmington
Exterior
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (171)
"Breakfast was easy and good options. "
United States
jessica
The price is AU$209
includes taxes & fees
1 Jan - 2 Jan 2026
Home2 Suites by Hilton Bristol
Property grounds
Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (102)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is AU$232
includes taxes & fees
26 Dec - 27 Dec
Truman Gillet House Bed & Breakfast
Deluxe Studio, Multiple Beds, Non Smoking
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very good, (1001)
"Room was clean, staff were nice."
United States
Stephen
The price is AU$128
includes taxes & fees
28 Dec - 29 Dec
Extended Stay America Suites Hartford Farmington
Front of property
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1003)
"Very nice room, pleasant and helpful staff"
United States
Concetta
The price is AU$299
includes taxes & fees
28 Dec - 29 Dec
Simsbury 1820 House
Library
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (165)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AU$282
includes taxes & fees
5 Jan - 6 Jan 2026
Blackberry River Inn
Lobby
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1003)
"Amazing stay"
United States
Marquise
The price is AU$238
includes taxes & fees
1 Jan - 2 Jan 2026
DoubleTree by Hilton Hotel Bristol, Connecticut
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (273)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is AU$301
includes taxes & fees
25 Dec - 26 Dec
Interlaken Inn & Resort
Interior
PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (178)
"Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50"
United States
David
The price is AU$126
includes taxes & fees
31 Dec - 1 Jan 2026
PLYMOUTH MOTOR LODGE
Executive lounge
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1004)
"So convenient for early departures, great rooms and friendly staff."
United States
Mark
The price is AU$393
includes taxes & fees
1 Jan - 2 Jan 2026
Sheraton Hartford Hotel at Bradley Airport
Terrace/patio
The Abner Hotel

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.2 out of 10, Wonderful, (46)
"Spacious room and friendly staff "
United States
Frank
The price is AU$373
includes taxes & fees
14 Jan - 15 Jan 2026
The Abner Hotel
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Cornwall Inn and Lodge

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is AU$363
includes taxes & fees
25 Dec - 26 Dec
Cornwall Inn and Lodge
Lobby sitting area
The Litchfield Inn

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.0 out of 10, Wonderful, (963)
"A delightful stay from beginning to end - clean, bright, beautiful in a lovely are of the state. "
United States
Lori
The price is AU$470
includes taxes & fees
1 Jan - 2 Jan 2026
The Litchfield 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.
See properties

Top Winchester Hotel Reviews

Recent Reviews in Winchester

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Front desk staff was very courteous and helpful. Room was very clean. There was something different each morning for breakfast. Will definitely stay here again. "
Cornealia 1-night trip
Posted 5 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 AU$126 per night from 31 Dec to 1 Jan
AU$126
31 Dec - 1 Jan 2026
includes taxes & fees
7.6/10 Good! (178 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 Extended Stay America Suites Hartford Farmington and Avon Old Farms Hotel. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Winchester is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a 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: Features a sauna, a seasonal outdoor pool and buffet. Hampton Inn & Suites Hartford/Farmington and Homewood Suites by Hilton Hartford-Farmington 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 Highland Lake, Burr Pond State Park and The Marina at Highland Lake. 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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