Search Winchester hotels

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
24 June - 25 June
Tomorrow
25 June - 26 June
This weekend
27 June - 29 June
Next weekend
4 July - 6 July

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Winchester

Sheraton Hartford Hotel at Bradley Airport
Executive lounge

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1005)
"It is adjacent to the airport so perfect for an early flight. Restaurant lounge food was excellent as well"
The price is AU$442
includes taxes & fees
29 June - 30 June
Sheraton Hartford Hotel at Bradley Airport
Delamar West Hartford
Lunch and dinner served

Delamar West Hartford

4.0 star property
9.8 out of 10, Exceptional, (987)
"Beautiful hotel"
Delamar West Hartford
Extended Stay America Suites Hartford Farmington
Deluxe Studio, Multiple Beds, Non Smoking

Extended Stay America Suites Hartford Farmington

2.5 star property
8.0 out of 10, Very good, (955)
"Friendly staff and clean rooms"
The price is AU$189
includes taxes & fees
13 July - 14 July
Extended Stay America Suites Hartford Farmington
Homewood Suites by Hilton Hartford-Farmington
BBQ/picnic area

Homewood Suites by Hilton Hartford-Farmington

3.0 star property
8.4 out of 10, Very good, (991)
"great location "
The price is AU$286
includes taxes & fees
30 June - 1 July
Homewood Suites by Hilton Hartford-Farmington
Hampton Inn & Suites Hartford/Farmington
Exterior

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1002)
"Staff was very friendly and prompt, whole facility was clean and nice, breakfast was delicious and the grounds were gorgeous. Will definitely stay there when traveling to that area again!"
The price is AU$262
includes taxes & fees
2 July - 3 July
Hampton Inn & Suites Hartford/Farmington
Fairfield Inn & Suites by Marriott Plainville
Lobby

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
8.6 out of 10, Excellent, (841)
"Very clean , comfortable beds and friendly staff "
The price is AU$186
includes taxes & fees
3 July - 4 July
Fairfield Inn & Suites by Marriott Plainville
The Farmington Inn & Suites
Staircase

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1002)
"We have stayed at the Farmington Inn many times and it has consistently been a positive experience! The rooms are comfortable and clean while the staff is friendly and accommodating. It is by far our favorite place to stay when visiting Farmington. "
The price is AU$283
includes taxes & fees
5 July - 6 July
The Farmington Inn & Suites
Avon Old Farms Hotel
Interior

Avon Old Farms Hotel

3.5 star property
8.4 out of 10, Very good, (1003)
"Lovely stay!"
The price is AU$333
includes taxes & fees
7 July - 8 July
Avon Old Farms Hotel
Simsbury 1820 House
Front of property

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (969)
"Great place to stay! "
The price is AU$361
includes taxes & fees
30 June - 1 July
Simsbury 1820 House
Simsbury Inn
Exterior

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (256)
"We got married here, & still live in the area. Love taking mini vacations to relax here, it’s wondeful"
The price is AU$439
includes taxes & fees
8 July - 9 July
Simsbury Inn
Residence Inn by Marriott Hartford Avon
Seasonal outdoor pool, pool umbrellas, pool loungers

Residence Inn by Marriott Hartford Avon

3.0 star property
8.8 out of 10, Excellent, (396)
"Beautiful scenery "
The price is AU$270
includes taxes & fees
13 July - 14 July
Residence Inn by Marriott Hartford Avon
Truman Gillet House Bed & Breakfast
Property grounds

Truman Gillet House Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (91)
"It was a lovely stay overnight with a delicious homemade breakfast. Very clean and hosts were so nice."
The price is AU$239
includes taxes & fees
30 June - 1 July
Truman Gillet House Bed & Breakfast
DoubleTree by Hilton Hotel Bristol, Connecticut
Lobby

DoubleTree by Hilton Hotel Bristol, Connecticut

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Clean environment "
The price is AU$285
includes taxes & fees
30 June - 1 July
DoubleTree by Hilton Hotel Bristol, Connecticut
Home2 Suites by Hilton Bristol
Exterior

Home2 Suites by Hilton Bristol

3.0 star property
9.4 out of 10, Exceptional, (90)
"Great facility"
The price is AU$270
includes taxes & fees
30 June - 1 July
Home2 Suites by Hilton Bristol
PLYMOUTH MOTOR LODGE
Interior

PLYMOUTH MOTOR LODGE

2.5 star property
7.8 out of 10, Good, (146)
"Nice location nice town and close to highways and shopping great staff and the owners are very friendly and helpful "
The price is AU$145
includes taxes & fees
7 July - 8 July
PLYMOUTH MOTOR LODGE
Argyll House by Boutique
Villa

Argyll House by Boutique

2.0 star property
The price is AU$4,553
includes taxes & fees
2 July - 3 July
Argyll House by Boutique
Days Inn by Wyndham Torrington
Exterior

Days Inn by Wyndham Torrington

2.0 star property
7.4 out of 10, Good, (1004)
"Location was good "
The price is AU$149
includes taxes & fees
13 July - 14 July
Days Inn by Wyndham Torrington
Americas Best Value Inn Torrington CT
Premium bedding, down duvets, Select Comfort beds, in-room safe

Americas Best Value Inn Torrington CT

2.5 star property
5.6 out of 10, (724)
"The accessible room was nice with large bathroom, plenty of grab bars, and a wheel chair accessible sink"
The price is AU$248
includes taxes & fees
7 July - 8 July
Americas Best Value Inn Torrington CT
The Abner Hotel
Terrace/patio

The Abner Hotel

3.0 star property
9.6 out of 10, Exceptional, (17)
"Beautiful property and great service."
The price is AU$419
includes taxes & fees
16 July - 17 July
The Abner Hotel
The Litchfield Inn
Lobby sitting area

The Litchfield Inn

4.0 star property
9.0 out of 10, Wonderful, (914)
"Wonderful Inn"
The price is AU$469
includes taxes & fees
29 June - 30 June
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Winchester

Check out the local area in Winchester—home to attractions like Highland Lake and Burr Pond State Park.

See all hotels in Winchester

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 Fairfield Inn & Suites by Marriott Plainville 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?

Beautiful retreat in a lake community to the enjoy the summer season. : This holiday home rental outside Winchester is located on a lake, and offers a BBQ, laundry facilities and a Smart TV to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. 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?

Fairfield Inn & Suites by Marriott Plainville: Features a snack bar/deli, a pool and daily. Avon Old Farms Hotel and DoubleTree by Hilton Hotel Bristol, Connecticut 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 Winchester Historical Society. A couple of additional sights to add to your itinerary are Platt Hill State Park and Laurel Lanes. 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.