Find hotels in Winchester, CT from ₩121,587

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Aug 10 - Aug 11
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Compare 672 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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, (976)
"Great place to stay and eat."
The price is ₩262,478
₩325,806 total
includes taxes & fees
Aug 11 - Aug 12
Simsbury 1820 House
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 ₩392,397
₩472,085 total
includes taxes & fees
Aug 24 - Aug 25
Delamar West Hartford
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, (1000)
"Great stay "
The price is ₩347,193
₩399,271 total
includes taxes & fees
Sep 1 - Sep 2
Sheraton Hartford Hotel at Bradley Airport
Locust Tree Bed and Breakfast LLC
Relax on the covered porch with two comfortable rocking chairs and lush green surroundings.

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (398)
"A positively delightful B&B in a beautiful town. "
The price is ₩145,821
₩167,694 total
includes taxes & fees
Aug 11 - Aug 12
Locust Tree Bed and Breakfast LLC
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, (263)
"Excellent all around. Staff could not have been more helpful."
The price is ₩318,028
₩396,077 total
includes taxes & fees
Aug 11 - Aug 12
Simsbury Inn
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 ₩194,428
₩215,815 total
includes taxes & fees
Aug 11 - Aug 12
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)
"Nice, clean, up to date. "
The price is ₩223,106
₩256,572 total
includes taxes & fees
Aug 24 - Aug 25
DoubleTree by Hilton Hotel Bristol, Connecticut
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, (870)
"Great stay would and will stay again "
The price is ₩133,322
₩153,320 total
includes taxes & fees
Sep 1 - Sep 2
Fairfield Inn & Suites by Marriott Plainville
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, (1001)
"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 ₩183,151
₩210,624 total
includes taxes & fees
Sep 4 - Sep 5
Hampton Inn & Suites Hartford/Farmington
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, (929)
"Wonderful Inn"
The price is ₩394,494
₩453,669 total
includes taxes & fees
Aug 11 - Aug 12
The Litchfield Inn
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, (1001)
"great location "
The price is ₩164,319
₩188,967 total
includes taxes & fees
Sep 1 - Sep 2
Homewood Suites by Hilton Hartford-Farmington
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, (1006)
"Great place stayed there 6 days in July."
The price is ₩179,151
₩229,980 total
includes taxes & fees
Aug 14 - Aug 15
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, (1004)
"We just ate at their dining/ bar and it was excellent - staff is extremely accommodating and friendly "
The price is ₩211,232
₩273,269 total
includes taxes & fees
Aug 11 - Aug 12
Avon Old Farms Hotel
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, (1000)
"Very comfortable for a weeks' stay. Good location "
The price is ₩121,587
₩139,825 total
includes taxes & fees
Sep 1 - Sep 2
Days Inn by Wyndham Torrington
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, (111)
"It was a great stay"
The price is ₩205,538
₩236,369 total
includes taxes & fees
Sep 1 - Sep 2
Home2 Suites by Hilton Bristol
Extended Stay America Suites Hartford Farmington
Deluxe Studio, Multiple Beds, Non Smoking | 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, (968)
"Great Place…"
The price is ₩137,474
₩158,097 total
includes taxes & fees
Aug 11 - Aug 12
Extended Stay America Suites Hartford Farmington
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, (30)
"This place is so fabulous! We love staying here and feel like the staff makes it even better. A stay here will not disappoint"
The price is ₩361,080
₩415,242 total
includes taxes & fees
Sep 1 - Sep 2
The Abner Hotel
Wilder House Berkshires
Cozy retreat with a large bed, bedside tables, and a chandelier.

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (28)
"Always perfect! "
The price is ₩239,979
₩268,060 total
includes taxes & fees
Sep 9 - Sep 10
Wilder House Berkshires
Blackberry River Inn
Cozy living room with a traditional fireplace, armchairs, and a sofa, perfect for relaxing.

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (123)
"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 ₩228,244
₩262,481 total
includes taxes & fees
Sep 2 - Sep 3
Blackberry River Inn
The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (88)
"Beautiful room and property. Perfect weekend getaway!"
The price is ₩402,743
₩485,986 total
includes taxes & fees
Aug 11 - Aug 12
The Old Inn On The Green
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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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

Blackberry River Inn

Blackberry River Inn

10/10 Excellent
"Wonderful breakfast with gluten free options. Beautiful spot/property. Pool was perfect. Clean and comfortable."
Diane 1-night trip
Posted 3 days ago
Blackberry River 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 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.