Winchester Hotels

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Top 10 trending Winchester hotels

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (977)
"Great place to stay and eat."
The price is €202
includes taxes & fees
21 Aug - 22 Aug
Simsbury 1820 House

Delamar West Hartford

4.0 star property
9.8 out of 10, Exceptional, (1000)
"Beautiful hotel, safe area, walk to shopping and restaurants. The staff was extremely nice and accommodating."
The price is €292
includes taxes & fees
24 Aug - 25 Aug
Delamar West Hartford

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1001)
"Great stay "
The price is €248
includes taxes & fees
1 Sept - 2 Sept
Sheraton Hartford Hotel at Bradley Airport

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (399)
"A positively delightful B&B in a beautiful town. "
The price is €104
includes taxes & fees
13 Aug - 14 Aug
Locust Tree Bed and Breakfast LLC

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 €245
includes taxes & fees
24 Aug - 25 Aug
Simsbury Inn

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 €133
includes taxes & fees
16 Aug - 17 Aug
Truman Gillet House Bed & Breakfast

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 €159
includes taxes & fees
24 Aug - 25 Aug
DoubleTree by Hilton Hotel Bristol, Connecticut

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
8.6 out of 10, Excellent, (873)
"Great stay would and will stay again "
The price is €104
includes taxes & fees
17 Aug - 18 Aug
Fairfield Inn & Suites by Marriott Plainville

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1002)
"Enjoyed my stay here. Very comfy bed and the room was spotless. "
The price is €131
includes taxes & fees
4 Sept - 5 Sept
Hampton Inn & Suites Hartford/Farmington

The Litchfield Inn

4.0 star property
9.0 out of 10, Wonderful, (931)
"Wonderful Inn"
The price is €302
includes taxes & fees
18 Aug - 19 Aug
The Litchfield Inn

Homewood Suites by Hilton Hartford-Farmington

3.0 star property
8.4 out of 10, Very good, (1002)
"great location "
The price is €117
includes taxes & fees
1 Sept - 2 Sept
Homewood Suites by Hilton Hartford-Farmington

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1001)
"Great place stayed there 6 days in July."
The price is €143
includes taxes & fees
14 Aug - 15 Aug
The Farmington Inn & Suites

Avon Old Farms Hotel

3.5 star property
8.4 out of 10, Very good, (1009)
"We just ate at their dining/ bar and it was excellent - staff is extremely accommodating and friendly "
The price is €169
includes taxes & fees
13 Aug - 14 Aug
Avon Old Farms Hotel

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 €87
includes taxes & fees
17 Aug - 18 Aug
Days Inn by Wyndham Torrington

Home2 Suites by Hilton Bristol

3.0 star property
9.4 out of 10, Exceptional, (115)
"It was a great stay"
The price is €143
includes taxes & fees
31 Aug - 1 Sept
Home2 Suites by Hilton Bristol

Extended Stay America Suites Hartford Farmington

2.5 star property
8.0 out of 10, Very good, (969)
"Great Place…"
The price is €107
includes taxes & fees
13 Aug - 14 Aug
Extended Stay America Suites Hartford Farmington

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 €273
includes taxes & fees
7 Sept - 8 Sept
The Abner Hotel

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (29)
"Always perfect! "
The price is €166
includes taxes & fees
9 Sept - 10 Sept
Wilder House Berkshires

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (124)
"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 €163
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn

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 €301
includes taxes & fees
13 Aug - 14 Aug
The Old Inn On The Green
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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

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.

What are some of the best holiday rentals that Winchester has to offer?

Big farmhouse in the foothills of the Berkshires: This holiday home rental outside of Winchester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books. See all 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.