Winchester Hotels from S$127

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22 Aug - 23 Aug
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22 Aug - 24 Aug
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Top 10 trending Winchester hotels

Our top choices for Winchester hotels

Delamar West Hartford
Lunch and dinner served

Delamar West Hartford

4.0 star property
9.8 out of 10, Exceptional, (1002)
"Beautiful hotel, safe area, walk to shopping and restaurants. The staff was extremely nice and accommodating."
The price is S$522
includes taxes & fees
24 Aug - 25 Aug
Delamar West Hartford
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 S$200
includes taxes & fees
27 Aug - 28 Aug
Truman Gillet House Bed & Breakfast
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$486
includes taxes & fees
8 Sept - 9 Sept
The White Hart
The Abner Hotel
Terrace/patio

The Abner Hotel

3.0 star property
9.6 out of 10, Exceptional, (32)
"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 S$408
includes taxes & fees
11 Sept - 12 Sept
The Abner Hotel
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 S$241
includes taxes & fees
9 Sept - 10 Sept
Wilder House Berkshires
Home2 Suites by Hilton Bristol
Exterior

Home2 Suites by Hilton Bristol

3.0 star property
9.4 out of 10, Exceptional, (121)
"It was a great stay"
The price is S$213
includes taxes & fees
31 Aug - 1 Sept
Home2 Suites by Hilton Bristol
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 S$243
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
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 S$272
includes taxes & fees
27 Aug - 28 Aug
Simsbury 1820 House
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, (88)
"Beautiful room and property. Perfect weekend getaway!"
The price is S$450
includes taxes & fees
24 Aug - 25 Aug
The Old Inn On The Green
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 S$367
includes taxes & fees
27 Aug - 28 Aug
Simsbury Inn
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (128)
"Great property"
Gedney Farm
Sheraton Hartford Hotel at Bradley Airport
Executive lounge

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1001)
"Great stay "
The price is S$370
includes taxes & fees
3 Sept - 4 Sept
Sheraton Hartford Hotel at Bradley Airport
Cornwall Inn and Lodge
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Cornwall Inn and Lodge

3.0 star property
9.2 out of 10, Wonderful, (138)
"Cozy small inn with everything needed. Surrounded by massive green and vintage looking lawn. "
The price is S$294
includes taxes & fees
25 Aug - 26 Aug
Cornwall Inn and Lodge
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (136)
"Excellent bed and breakfast, room was clean and comfortable."
The price is S$405
includes taxes & fees
26 Aug - 27 Aug
Manor House Inn
Mayflower Inn & Spa, Auberge Resorts Collection
Couples treatment room(s), steam room, body treatments, aromatherapy

Mayflower Inn & Spa, Auberge Resorts Collection

5.0 star property
9.2 out of 10, Wonderful, (53)
"Incredible place - will definitely return. "
The price is S$1,501
includes taxes & fees
2 Sept - 3 Sept
Mayflower Inn & Spa, Auberge Resorts Collection
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 S$237
includes taxes & fees
1 Sept - 2 Sept
DoubleTree by Hilton Hotel Bristol, Connecticut
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 S$155
includes taxes & fees
24 Aug - 25 Aug
Locust Tree Bed and Breakfast LLC
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 S$413
includes taxes & fees
24 Aug - 25 Aug
The Litchfield Inn
The Farmington Inn & Suites
Staircase

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1002)
"Great place stayed there 6 days in July."
The price is S$215
includes taxes & fees
27 Aug - 28 Aug
The Farmington Inn & Suites
Residence Inn by Marriott Hartford Avon
Seasonal outdoor pool, pool umbrellas, pool 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 S$212
includes taxes & fees
4 Sept - 5 Sept
Residence Inn by Marriott Hartford Avon
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"My only complaint is your parking garage. It is terrifyingly dark. Had I been alone? I'd never have parked there!!! "
Margaret 1-night trip
Posted 1 day ago
Sheraton Hartford Hotel at Bradley Airport

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 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, 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 Homewood Suites by Hilton 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?

Favourite places to visit include Highland Lake, Burr Pond State Park and Platt Hill State Park. A couple of additional sights to add to your itinerary are Winchester Historical Society and Laurel Lanes. 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.