Find hotels in Winchester, CT from Rp1.441.835

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

Filter by

Guest rating
Guest rating
Star rating

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 Rp1.583.853
Rp1.821.431 total
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, (913)
"Great place stayed several times."
United States
Marlene D
The price is Rp1.609.440
Rp1.850.856 total
includes taxes & fees
3 Jan - 4 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 Rp1.760.325
Rp2.024.374 total
includes taxes & fees
29 Dec - 30 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 Rp1.659.735
Rp2.197.892 total
includes taxes & fees
29 Dec - 30 Dec
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 Rp2.048.348
Rp2.355.600 total
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 Rp1.980.785
Rp2.277.903 total
includes taxes & fees
8 Jan - 9 Jan 2026
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 Rp1.563.336
Rp2.164.194 total
includes taxes & fees
30 Dec - 31 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 Rp2.054.729
Rp2.362.939 total
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 Rp2.048.014
Rp2.355.216 total
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 Rp2.347.100
Rp2.605.281 total
includes taxes & fees
29 Dec - 30 Dec
Truman Gillet House Bed & Breakfast
Deluxe Studio, Multiple Beds, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets
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 Rp1.253.821
Rp1.441.835 total
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, (1000)
"Very nice room, pleasant and helpful staff"
United States
Concetta
The price is Rp2.665.635
Rp3.354.677 total
includes taxes & fees
29 Dec - 30 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 Rp2.755.328
Rp3.168.627 total
includes taxes & fees
8 Jan - 9 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 Rp2.326.342
Rp2.675.293 total
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 Rp3.002.611
Rp3.453.003 total
includes taxes & fees
1 Jan - 2 Jan 2026
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 Rp1.341.200
Rp1.542.380 total
includes taxes & fees
29 Dec - 30 Dec
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 Rp3.844.223
Rp4.420.856 total
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 Rp3.643.035
Rp4.189.574 total
includes taxes & fees
19 Jan - 20 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 Rp3.547.474
Rp4.079.595 total
includes taxes & fees
27 Dec - 28 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 Rp4.598.967
Rp5.288.744 total
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"So convenient for early departures, great rooms and friendly staff."
Mark 1-night trip
Posted 6 days ago
Sheraton Hartford Hotel at Bradley Airport
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Staff was very friendly, grounds are impeccable. Food was great, room was very nice. Absolutely amazing experience "
Kent Allen 4-night trip
Posted 1 month ago
Mayflower Inn & Spa, Auberge Collection

More cheap stays in Winchester

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
The price is Rp1.253.821 per night from 28 Dec to 29 Dec
Rp1.253.821
Rp1.441.835 total
28 Dec - 29 Dec
includes taxes & fees
7.8/10 Good! (1,005 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.
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.