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30 Jul - 31 Jul
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Top 10 Winchester hotels and places to stay

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, (974)
"Great place to stay and eat."
The price is ฿6,127
฿7,606 total
includes taxes & fees
31 Jul - 1 Aug
Simsbury 1820 House
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, (106)
"It was a great stay"
The price is ฿4,668
฿5,369 total
includes taxes & fees
24 Aug - 25 Aug
Home2 Suites by Hilton Bristol
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, (120)
"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 ฿5,390
฿6,198 total
includes taxes & fees
4 Aug - 5 Aug
Blackberry River Inn
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, (1000)
"Lovely stay!"
The price is ฿4,931
฿6,379 total
includes taxes & fees
31 Jul - 1 Aug
Avon Old Farms Hotel
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, (151)
"Good stay for an overnight stop"
The price is ฿2,594
฿2,983 total
includes taxes & fees
4 Aug - 5 Aug
PLYMOUTH MOTOR LODGE
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, (262)
"Excellent all around. Staff could not have been more helpful."
The price is ฿7,424
฿9,246 total
includes taxes & fees
3 Aug - 4 Aug
Simsbury Inn
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, (864)
"Great stay would and will stay again "
The price is ฿3,112
฿3,579 total
includes taxes & fees
14 Aug - 15 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)
"Comfortable beds clean room needs a little updating in bathroom "
The price is ฿4,182
฿5,369 total
includes taxes & fees
31 Jul - 1 Aug
The Farmington Inn & Suites
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, (1008)
"Great stay "
The price is ฿9,045
฿10,402 total
includes taxes & fees
10 Aug - 11 Aug
Sheraton Hartford Hotel at Bradley Airport
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, (27)
"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 ฿7,651
฿8,799 total
includes taxes & fees
24 Aug - 25 Aug
The Abner Hotel
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, (1000)
"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 ฿4,547
฿5,229 total
includes taxes & fees
14 Aug - 15 Aug
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, (927)
"Wonderful Inn"
The price is ฿9,212
฿10,594 total
includes taxes & fees
31 Jul - 1 Aug
The Litchfield Inn
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, (1000)
"Excellent location and beautiful property. "
The price is ฿9,160
฿11,020 total
includes taxes & fees
24 Aug - 25 Aug
Delamar West Hartford
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, (1000)
"great location "
The price is ฿4,657
฿5,356 total
includes taxes & fees
10 Aug - 11 Aug
Homewood Suites by Hilton Hartford-Farmington
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 ฿4,539
฿5,038 total
includes taxes & fees
1 Aug - 2 Aug
Truman Gillet House Bed & Breakfast
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, (1006)
"Had a great one-night stay here — they let me check in early too, which was much appreciated! "
The price is ฿3,224
฿3,708 total
includes taxes & fees
26 Aug - 27 Aug
Days Inn by Wyndham Torrington
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, (1004)
"Nice, clean, up to date. "
The price is ฿5,108
฿5,874 total
includes taxes & fees
14 Aug - 15 Aug
DoubleTree by Hilton Hotel Bristol, Connecticut
Hitching Post Country Motel
Experience the tranquil atmosphere of the Hitching Post Motel, surrounded by lush greenery and beautifully maintained gardens.

Hitching Post Country Motel

2.5 star property
6.6 out of 10, (59)
"For a low budget hotel, it was everything I could ask for Clean room, comfortable bed Wi-Fi very good service It’s not the four seasons, and I didn’t expect it to be"
The price is ฿4,214
฿4,847 total
includes taxes & fees
3 Aug - 4 Aug
Hitching Post Country Motel
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, (397)
"Easy parking, great location!"
The price is ฿4,666
฿5,366 total
includes taxes & fees
17 Aug - 18 Aug
Residence Inn by Marriott Hartford Avon
Cornwall Inn and Lodge
Relax by the serene pool surrounded by lush greenery and comfortable seating.

Cornwall Inn and Lodge

3.0 star property
9.2 out of 10, Wonderful, (136)
"Cozy small inn with everything needed. Surrounded by massive green and vintage looking lawn. "
The price is ฿6,451
฿7,419 total
includes taxes & fees
31 Jul - 1 Aug
Cornwall Inn and Lodge
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

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 Abner Hotel

The Abner Hotel

10/10 Excellent
"all good"
Catherine 1-night trip
Posted 2 days ago
The Abner Hotel

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.

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.