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
23 Jul - 24 Jul
Tomorrow
24 Jul - 25 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Winchester

Sheraton Hartford Hotel at Bradley Airport
Relax in the living area with a sofa, armchairs, and a coffee table, offering a view of the ocean.

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1004)
"Great stay "
The price is NZ$515
includes taxes & fees
27 July - 28 July
Sheraton Hartford Hotel at Bradley Airport
Delamar West Hartford
Enjoy dining al fresco amidst lush greenery and rustic charm.

Delamar West Hartford

4.0 star property
9.8 out of 10, Exceptional, (1001)
"Excellent location and beautiful property. "
The price is NZ$603
includes taxes & fees
27 July - 28 July
Delamar West Hartford
Extended Stay America Suites Hartford Farmington
Relax in a cozy space with a flat-screen TV, comfortable sofa, and dining area.

Extended Stay America Suites Hartford Farmington

2.5 star property
8.0 out of 10, Very good, (963)
"I enjoyed my stay. It was a little home away from home."
The price is NZ$222
includes taxes & fees
10 Aug - 11 Aug
Extended Stay America Suites Hartford Farmington
Homewood Suites by Hilton Hartford-Farmington
Stroll through the serene courtyard, surrounded by well-maintained hedges and flowering shrubs, and enjoy the views from the large windows.

Homewood Suites by Hilton Hartford-Farmington

3.0 star property
8.4 out of 10, Very good, (998)
"great location "
The price is NZ$275
includes taxes & fees
10 Aug - 11 Aug
Homewood Suites by Hilton Hartford-Farmington
Hampton Inn & Suites Hartford/Farmington
Stroll through the beautifully landscaped grounds, featuring a central entrance, walkway, and serene waterfall.

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1004)
"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 NZ$274
includes taxes & fees
14 Aug - 15 Aug
Hampton Inn & Suites Hartford/Farmington
Fairfield Inn & Suites by Marriott Plainville
Guests can relax on the sofas and enjoy the natural ambiance of the lobby, featuring a large potted plant and pendant lights.

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
8.6 out of 10, Excellent, (860)
"Great stay would and will stay again "
The price is NZ$184
includes taxes & fees
10 Aug - 11 Aug
Fairfield Inn & Suites by Marriott Plainville
The Farmington Inn & Suites
Stunning interior with a grand staircase, ornate chandelier, and classic wooden chest.

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1000)
"The best "
The price is NZ$259
includes taxes & fees
10 Aug - 11 Aug
The Farmington Inn & Suites
Avon Old Farms Hotel
Experience the grandeur of our lobby, featuring a grand staircase, elegant chandeliers, and beautiful artwork.

Avon Old Farms Hotel

3.5 star property
8.4 out of 10, Very good, (1006)
"Lovely stay!"
The price is NZ$328
includes taxes & fees
5 Aug - 6 Aug
Avon Old Farms Hotel
Simsbury 1820 House
Stately home with a central entrance and columns, surrounded by lush gardens.

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (972)
"Great place to stay and eat."
The price is NZ$391
includes taxes & fees
24 July - 25 July
Simsbury 1820 House
Simsbury Inn
Stroll through the serene garden, surrounded by lush greenery and a central fountain.

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (260)
"We got married here, & still live in the area. Love taking mini vacations to relax here, it’s wondeful"
The price is NZ$471
includes taxes & fees
27 July - 28 July
Simsbury Inn
Residence Inn by Marriott Hartford Avon
Relax by the rectangular pool surrounded by lounge chairs and a small table.

Residence Inn by Marriott Hartford Avon

3.0 star property
8.8 out of 10, Excellent, (396)
"Easy parking, great location!"
The price is NZ$275
includes taxes & fees
17 Aug - 18 Aug
Residence Inn by Marriott Hartford Avon
Truman Gillet House Bed & Breakfast
Welcome to a charming winter retreat with a cozy porch and inviting outdoor space.

Truman Gillet House Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (93)
"It was a lovely stay overnight with a delicious homemade breakfast. Very clean and hosts were so nice."
The price is NZ$259
includes taxes & fees
28 July - 29 July
Truman Gillet House Bed & Breakfast
DoubleTree by Hilton Hotel Bristol, Connecticut
Relax in our spacious lobby with large windows, pendant lights, and a central potted plant.

DoubleTree by Hilton Hotel Bristol, Connecticut

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Pool, hot tub, restaurant onsite. Near fun activities for kids. Great spot. Would return."
The price is NZ$301
includes taxes & fees
17 Aug - 18 Aug
DoubleTree by Hilton Hotel Bristol, Connecticut
Home2 Suites by Hilton Bristol
Home2 Suites by Hilton features a contemporary design with a flat roof and a mix of brick and glass facade.

Home2 Suites by Hilton Bristol

3.0 star property
9.4 out of 10, Exceptional, (103)
"It was a great stay"
The price is NZ$291
includes taxes & fees
31 July - 1 Aug
Home2 Suites by Hilton Bristol
PLYMOUTH MOTOR LODGE
Cozy retreat with a desk, flat-screen TV, and comfortable seating area.

PLYMOUTH MOTOR LODGE

2.5 star property
7.8 out of 10, Good, (149)
"Good stay for an overnight stop"
The price is NZ$141
includes taxes & fees
24 July - 25 July
PLYMOUTH MOTOR LODGE
Argyll House by Boutique
Surrounded by lush greenery, this traditional building offers a serene and inviting atmosphere.

Argyll House by Boutique

2.0 star property
The price is NZ$4,720
includes taxes & fees
31 July - 1 Aug
Argyll House by Boutique
Days Inn by Wyndham Torrington
Experience the comfort of a convenient hotel stay with a flat facade, covered entrance, and on-site parking.

Days Inn by Wyndham Torrington

2.0 star property
7.4 out of 10, Good, (1004)
"Had a great one-night stay here — they let me check in early too, which was much appreciated! "
The price is NZ$191
includes taxes & fees
17 Aug - 18 Aug
Days Inn by Wyndham Torrington
Americas Best Value Inn Torrington CT
Comfortable accommodations feature a large bed, nightstand, and desk with chair.

Americas Best Value Inn Torrington CT

2.5 star property
5.6 out of 10, (738)
"Tina, front desk rep, was lovely & helpful. She was the best part of our overnight stay."
The price is NZ$207
includes taxes & fees
6 Aug - 7 Aug
Americas Best Value Inn Torrington CT
The Abner Hotel
Enjoy a casual dining experience with a view from this outdoor patio area, featuring tables, chairs, and lush greenery.

The Abner Hotel

3.0 star property
9.6 out of 10, Exceptional, (24)
"Beautiful property and great service."
The price is NZ$468
includes taxes & fees
13 Aug - 14 Aug
The Abner Hotel
The Litchfield Inn
Cozy living room with a fireplace, television, and large window.

The Litchfield Inn

4.0 star property
9.0 out of 10, Wonderful, (924)
"Wonderful Inn"
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

Top Winchester Hotel Reviews

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Extremely clean and cozy. Super nice owner and staff! If we are ever in the area again wouldn’t hesitate to go back. Super cozy and exceptionally clean hotel with nice and professional staff. Look no further!!! "
Yana 1-night trip
Posted 2 days ago
The Litchfield Inn

Frequently asked questions

What's the best place for a stay in Winchester?

The Farmington Inn & Suites, located 20.6 mi (33.1 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 Avon Old Farms Hotel 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?

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: Provides a sauna, a seasonal outdoor pool and buffet. Fairfield Inn & Suites by Marriott Plainville and Hampton Inn & Suites 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?

The picturesque setting of Highland Lake and Rowley Fields exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Burr Pond State Park 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.