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
Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 22 - Aug 24
Next weekend
Aug 29 - Aug 31

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winchester hotels

Our top choices for Winchester hotels

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (400)
"A positively delightful B&B in a beautiful town. "
The price is P5,983
P6,881 total
includes taxes & fees
Aug 28 - Aug 29
Locust Tree Bed and Breakfast LLC
Days Inn by Wyndham Torrington
Exterior

Days Inn by Wyndham Torrington

2.0 star property
7.4 out of 10, Good, (1000)
"Very comfortable for a weeks' stay. Good location "
The price is P4,903
P5,639 total
includes taxes & fees
Sep 4 - Sep 5
Days Inn by Wyndham Torrington
PLYMOUTH MOTOR LODGE
Interior

PLYMOUTH MOTOR LODGE

2.5 star property
7.8 out of 10, Good, (154)
"Good stay for an overnight stop"
The price is P4,559
P5,242 total
includes taxes & fees
Aug 26 - Aug 27
PLYMOUTH MOTOR LODGE
Simsbury 1820 House
Front of property

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (980)
"Great place to stay and eat."
The price is P9,630
P12,057 total
includes taxes & fees
Aug 28 - Aug 29
Simsbury 1820 House
Fairfield Inn & Suites by Marriott Plainville
Lobby

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
8.6 out of 10, Excellent, (875)
"Great stay would and will stay again "
The price is P5,470
P6,291 total
includes taxes & fees
Sep 14 - Sep 15
Fairfield Inn & Suites by Marriott Plainville
Truman Gillet House Bed & Breakfast
Property grounds

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 P7,977
P8,855 total
includes taxes & fees
Aug 24 - Aug 25
Truman Gillet House Bed & Breakfast
Extended Stay America Suites Hartford Farmington
Desk, iron/ironing board, free WiFi, bed sheets

Extended Stay America Suites Hartford Farmington

2.5 star property
8.0 out of 10, Very Good, (976)
"Had a great time, clean, quiet, staff respectful."
The price is P6,579
P7,566 total
includes taxes & fees
Sep 3 - Sep 4
Extended Stay America Suites Hartford Farmington
Elm Motel
Reception

Elm Motel

2.0 star property
7.2 out of 10, Good, (123)
"Very clean, lacking bathroom and bathroom storage. Good price."
The price is P5,071
P5,665 total
includes taxes & fees
Aug 31 - Sep 1
Elm Motel
The Farmington Inn & Suites
Staircase

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1001)
"Great place stayed there 6 days in July."
The price is P7,921
P10,092 total
includes taxes & fees
Aug 26 - Aug 27
The Farmington Inn & Suites
Hampton Inn & Suites Hartford/Farmington
Exterior

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1001)
"Nice staff and good location"
The price is P7,488
P8,611 total
includes taxes & fees
Sep 4 - Sep 5
Hampton Inn & Suites Hartford/Farmington
Avon Old Farms Hotel
Interior

Avon Old Farms Hotel

3.5 star property
8.4 out of 10, Very Good, (1001)
"We just ate at their dining/ bar and it was excellent - staff is extremely accommodating and friendly "
The price is P7,641
P10,033 total
includes taxes & fees
Aug 24 - Aug 25
Avon Old Farms Hotel
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, (1001)
"great location "
The price is P6,732
P7,742 total
includes taxes & fees
Sep 1 - Sep 2
Homewood Suites by Hilton Hartford-Farmington
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (127)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is P9,365
P10,770 total
includes taxes & fees
Sep 15 - Sep 16
Blackberry River Inn
Sheraton Hartford Hotel at Bradley Airport
Executive lounge

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1000)
"Great stay "
The price is P14,246
P16,382 total
includes taxes & fees
Sep 2 - Sep 3
Sheraton Hartford Hotel at Bradley Airport
Home2 Suites by Hilton Bristol
Exterior

Home2 Suites by Hilton Bristol

3.0 star property
9.4 out of 10, Exceptional, (118)
"It was a great stay"
The price is P8,205
P9,436 total
includes taxes & fees
Aug 31 - Sep 1
Home2 Suites by Hilton Bristol
DoubleTree by Hilton Hotel Bristol, Connecticut
Lobby

DoubleTree by Hilton Hotel Bristol, Connecticut

4.0 star property
9.0 out of 10, Wonderful, (1000)
"Great facilities and service. Pool and fitness center were great. "
The price is P9,154
P10,527 total
includes taxes & fees
Sep 1 - Sep 2
DoubleTree by Hilton Hotel Bristol, Connecticut
The Litchfield Inn
Lobby sitting area

The Litchfield Inn

4.0 star property
9.0 out of 10, Wonderful, (931)
"Wonderful Inn"
The price is P15,976
P18,372 total
includes taxes & fees
Aug 24 - Aug 25
The Litchfield Inn
Wilder House Berkshires
1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (29)
"Brads and Lara both served a fabulous breakfast. So friendly and welcoming! The bed was very comfortable. Only complaint was that the cabinet, closet door needs to be greased with WD 40 please on the hinges! A terrible & loud screeching noise!"
The price is P9,869
P11,024 total
includes taxes & fees
Sep 9 - Sep 10
Wilder House Berkshires
Residence Inn by Marriott Hartford Avon
Seasonal outdoor pool, pool umbrellas, sun loungers

Residence Inn by Marriott Hartford Avon

3.0 star property
8.8 out of 10, Excellent, (400)
"The pool was sub par"
The price is P8,185
P9,413 total
includes taxes & fees
Sep 1 - Sep 2
Residence Inn by Marriott Hartford Avon
Simsbury Inn
Exterior

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (266)
"Lovely property Everyone kind and gracious. "
The price is P13,049
P16,251 total
includes taxes & fees
Sep 1 - Sep 2
Simsbury 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

Venture to sights like Highland Lake and Burr Pond State Park as you discover Winchester.

See all hotels in Winchester

Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Great facilities and service. Pool and fitness center were great. "
Michelle 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Bristol, Connecticut

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 traveler data. Other good choices for your visit to the area are Avon Old Farms Hotel and Sheraton Hartford Hotel at Bradley Airport. 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! You'll find that most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.

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 Homewood Suites by Hilton Hartford-Farmington are two additional hotels with an onsite pool. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors to Winchester are sure to find plenty to explore and enjoy. In Winchester, there are 17 hotels and other accommodations to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

Favorite places to visit include Highland Lake, Burr Pond State Park, and Platt Hill State Park. A couple of additional sights to add to your agenda are Winchester Historical Society and Laurel Lanes. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.