Winchester Hotels from S$108

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15 Jul - 16 Jul
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Top 10 trending Winchester hotels

Delamar West Hartford
Lunch and dinner served

Delamar West Hartford

4.0 star property
9.8 out of 10, Exceptional, (996)
"Excellent location and beautiful property. "
The price is S$478
includes taxes & fees
3 Aug - 4 Aug
Delamar West Hartford
Simsbury 1820 House
Front of property

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (972)
"Great place to stay and eat."
The price is S$300
includes taxes & fees
21 Jul - 22 Jul
Simsbury 1820 House
The Farmington Inn & Suites
Staircase

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1000)
"dining near by"
The price is S$226
includes taxes & fees
16 Jul - 17 Jul
The Farmington Inn & Suites
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (116)
"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 S$245
includes taxes & fees
21 Jul - 22 Jul
Blackberry River Inn
The Litchfield Inn
Lobby sitting area

The Litchfield Inn

4.0 star property
9.0 out of 10, Wonderful, (919)
"Wonderful Inn"
The price is S$419
includes taxes & fees
4 Aug - 5 Aug
The Litchfield Inn
DoubleTree by Hilton Hotel Bristol, Connecticut
Lobby

DoubleTree by Hilton Hotel Bristol, Connecticut

4.0 star property
9.0 out of 10, Wonderful, (1003)
" Very clean. Restaurant in hotel excellent! Quiet at night. "
The price is S$237
includes taxes & fees
24 Jul - 25 Jul
DoubleTree by Hilton Hotel Bristol, Connecticut
Simsbury Inn
Exterior

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 S$365
includes taxes & fees
20 Jul - 21 Jul
Simsbury Inn
Avon Old Farms Hotel
Interior

Avon Old Farms Hotel

3.5 star property
8.4 out of 10, Very good, (1004)
"Lovely stay!"
The price is S$252
includes taxes & fees
28 Jul - 29 Jul
Avon Old Farms Hotel
The White Hart
1 bedroom, minibar, desk, iron/ironing board

The White Hart

4.0 star property
9.6 out of 10, Exceptional, (137)
"Restaurant was fabulous. Rooms were quaint and comfortable. Staff was excellent "
The price is S$453
includes taxes & fees
22 Jul - 23 Jul
The White Hart
Wilder House Berkshires
1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (26)
"Always perfect! "
The price is S$283
includes taxes & fees
30 Jul - 31 Jul
Wilder House Berkshires
The Old Inn On The Green
Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (86)
"Beautiful room and property. Perfect weekend getaway!"
The price is S$449
includes taxes & fees
16 Jul - 17 Jul
The Old Inn On The Green
Truman Gillet House Bed & Breakfast
Property grounds

Truman Gillet House Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (92)
"It was a lovely stay overnight with a delicious homemade breakfast. Very clean and hosts were so nice."
The price is S$199
includes taxes & fees
28 Jul - 29 Jul
Truman Gillet House Bed & Breakfast
Home2 Suites by Hilton Bristol
Exterior

Home2 Suites by Hilton Bristol

3.0 star property
9.4 out of 10, Exceptional, (102)
"It was a great stay"
The price is S$224
includes taxes & fees
31 Jul - 1 Aug
Home2 Suites by Hilton Bristol
Fairfield Inn & Suites by Marriott Plainville
Lobby

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
8.6 out of 10, Excellent, (852)
"Right off the highway great location"
The price is S$155
includes taxes & fees
20 Jul - 21 Jul
Fairfield Inn & Suites by Marriott Plainville
9 Academy
1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds

9 Academy

4.0 star property
9.6 out of 10, Exceptional, (5)
"The Loft was so beautifully decorated and every detail was perfect. "
The price is S$830
includes taxes & fees
16 Jul - 17 Jul
9 Academy
Sheraton Hartford Hotel at Bradley Airport
Executive lounge

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1009)
"Great stay "
The price is S$361
includes taxes & fees
1 Aug - 2 Aug
Sheraton Hartford Hotel at Bradley Airport
Interlaken Inn & Resort
Porch

Interlaken Inn & Resort

3.5 star property
8.2 out of 10, Very good, (252)
"Always a pleasure to stay at Interlaken. Great service, good food, quite location."
The price is S$370
includes taxes & fees
28 Jul - 29 Jul
Interlaken Inn & Resort
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"Excellent bed and breakfast, room was clean and comfortable."
The price is S$421
includes taxes & fees
23 Jul - 24 Jul
Manor House Inn
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (121)
"Beautiful, clean property that is well run."
Gedney Farm
Hampton Inn & Suites Hartford/Farmington
Exterior

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1003)
"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 S$217
includes taxes & fees
14 Aug - 15 Aug
Hampton Inn & Suites Hartford/Farmington
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

Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"Love the coffee machine! Love the staff! Loved my stay!"
Kathleen 2-night trip
Posted 2 days ago
Delamar West Hartford

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 Winchester Historical Society. 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.