Winchester Hotels from S$112

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Top 10 trending Winchester hotels

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (981)
"Great place to stay and eat."
The price is S$272
includes taxes & fees
27 Aug - 28 Aug
Simsbury 1820 House

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (401)
"Peaceful area and great staff; Thank you for the service and experience "
The price is S$155
includes taxes & fees
27 Aug - 28 Aug
Locust Tree Bed and Breakfast LLC

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

Days Inn by Wyndham Torrington

2.0 star property
7.4 out of 10, Good, (1001)
"Very comfortable for a weeks' stay. Good location "
The price is S$129
includes taxes & fees
3 Sept - 4 Sept
Days Inn by Wyndham Torrington

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1000)
"Very nice area, friendly Service, best Eagles for breakfast"
The price is S$207
includes taxes & fees
4 Sept - 5 Sept
The Farmington Inn & Suites

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
8.6 out of 10, Excellent, (879)
"Great stay would and will stay again "
The price is S$142
includes taxes & fees
14 Sept - 15 Sept
Fairfield Inn & Suites by Marriott Plainville

Avon Old Farms Hotel

3.5 star property
8.4 out of 10, Very good, (1006)
"We just ate at their dining/ bar and it was excellent - staff is extremely accommodating and friendly "
The price is S$226
includes taxes & fees
27 Aug - 28 Aug
Avon Old Farms Hotel

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1004)
"Great stay "
The price is S$370
includes taxes & fees
1 Sept - 2 Sept
Sheraton Hartford Hotel at Bradley Airport

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1003)
"Nice staff and good location"
The price is S$193
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Hartford/Farmington

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$230
includes taxes & fees
10 Sept - 11 Sept
Wilder House Berkshires

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (266)
"Lovely property Everyone kind and gracious. "
The price is S$365
includes taxes & fees
8 Sept - 9 Sept
Simsbury Inn

The Litchfield Inn

4.0 star property
9.0 out of 10, Wonderful, (933)
"Wonderful Inn"
The Litchfield Inn

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

PLYMOUTH MOTOR LODGE

2.5 star property
7.8 out of 10, Good, (156)
"Good stay for an overnight stop"
The price is S$112
includes taxes & fees
27 Aug - 28 Aug
PLYMOUTH MOTOR LODGE

Home2 Suites by Hilton Bristol

3.0 star property
9.4 out of 10, Exceptional, (122)
"It was a great stay"
The price is S$219
includes taxes & fees
1 Sept - 2 Sept
Home2 Suites by Hilton Bristol

Homewood Suites by Hilton Hartford-Farmington

3.0 star property
8.4 out of 10, Very good, (1002)
"great location "
The price is S$176
includes taxes & fees
1 Sept - 2 Sept
Homewood Suites by Hilton Hartford-Farmington

DoubleTree by Hilton Hotel Bristol, Connecticut

4.0 star property
9.0 out of 10, Wonderful, (1004)
"Great facilities and service. Pool and fitness center were great. "
The price is S$238
includes taxes & fees
1 Sept - 2 Sept
DoubleTree by Hilton Hotel Bristol, Connecticut

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
27 Aug - 28 Aug
Cornwall Inn and Lodge

The Abner Hotel

3.0 star property
9.6 out of 10, Exceptional, (33)
"Beautiful property and great service."
The price is S$418
includes taxes & fees
16 Sept - 17 Sept
The Abner Hotel

Residence Inn by Marriott Hartford Avon

3.0 star property
8.8 out of 10, Excellent, (403)
"The pool was sub par"
The price is S$175
includes taxes & fees
2 Sept - 3 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.

Top Winchester Hotel Reviews

More cheap stays in Winchester

More cheap stays in Winchester

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.