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16 Aug - 17 Aug
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Top 10 trending Winchester hotels

DoubleTree by Hilton Hotel Bristol, Connecticut
Lobby

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 €158
includes taxes & fees
24 Aug - 25 Aug
DoubleTree by Hilton Hotel Bristol, Connecticut
Extended Stay America Suites Hartford Farmington
Deluxe Studio, Multiple Beds, Non Smoking

Extended Stay America Suites Hartford Farmington

2.5 star property
8.0 out of 10, Very good, (971)
"Great Place…"
The price is €88
includes taxes & fees
17 Aug - 18 Aug
Extended Stay America Suites Hartford Farmington
Home2 Suites by Hilton Bristol
Exterior

Home2 Suites by Hilton Bristol

3.0 star property
9.4 out of 10, Exceptional, (115)
"It was a great stay"
The price is €142
includes taxes & fees
31 Aug - 1 Sept
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, (874)
"Great stay would and will stay again "
The price is €94
includes taxes & fees
1 Sept - 2 Sept
Fairfield Inn & Suites by Marriott Plainville
Homewood Suites by Hilton Hartford-Farmington
BBQ/picnic Area

Homewood Suites by Hilton Hartford-Farmington

3.0 star property
8.4 out of 10, Very good, (1000)
"great location "
The price is €116
includes taxes & fees
1 Sept - 2 Sept
Homewood Suites by Hilton Hartford-Farmington
Hampton Inn & Suites Hartford/Farmington
Exterior

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1002)
"Nice staff and good location"
The price is €126
includes taxes & fees
4 Sept - 5 Sept
Hampton Inn & Suites Hartford/Farmington
Simsbury Inn
Exterior

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (264)
"Excellent all around. Staff could not have been more helpful."
The price is €244
includes taxes & fees
17 Aug - 18 Aug
Simsbury Inn
Days Inn by Wyndham Torrington
Exterior

Days Inn by Wyndham Torrington

2.0 star property
7.4 out of 10, Good, (1002)
"Very comfortable for a weeks' stay. Good location "
The price is €89
includes taxes & fees
24 Aug - 25 Aug
Days Inn by Wyndham Torrington
Avon Old Farms Hotel
Interior

Avon Old Farms Hotel

3.5 star property
8.4 out of 10, Very good, (1001)
"We just ate at their dining/ bar and it was excellent - staff is extremely accommodating and friendly "
The price is €150
includes taxes & fees
24 Aug - 25 Aug
Avon Old Farms Hotel
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, (399)
"Easy parking, great location!"
The price is €133
includes taxes & fees
14 Sept - 15 Sept
Residence Inn by Marriott Hartford Avon
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 €937
includes taxes & fees
26 Aug - 27 Aug
Mayflower Inn & Spa, Auberge Resorts Collection
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 €275
includes taxes & fees
24 Aug - 25 Aug
The Litchfield Inn
Locust Tree Bed and Breakfast LLC
Terrace/patio

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 €103
includes taxes & fees
18 Aug - 19 Aug
Locust Tree Bed and Breakfast LLC
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 €142
includes taxes & fees
17 Aug - 18 Aug
The Farmington Inn & Suites
The Abner Hotel
Terrace/patio

The Abner Hotel

3.0 star property
9.6 out of 10, Exceptional, (31)
"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 €271
includes taxes & fees
7 Sept - 8 Sept
The Abner Hotel
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (125)
"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 €162
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
Sheraton Hartford Hotel at Bradley Airport
Executive lounge

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1002)
"Great stay "
The price is €246
includes taxes & fees
1 Sept - 2 Sept
Sheraton Hartford Hotel at Bradley Airport
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 €318
includes taxes & fees
24 Aug - 25 Aug
Delamar West Hartford
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, (137)
"Cozy small inn with everything needed. Surrounded by massive green and vintage looking lawn. "
The price is €196
includes taxes & fees
18 Aug - 19 Aug
Cornwall Inn and Lodge
Americas Best Value Inn Torrington CT
Premium bedding, down duvets, Select Comfort beds, in-room safe

Americas Best Value Inn Torrington CT

2.5 star property
5.6 out of 10, (744)
"Tina, front desk rep, was lovely & helpful. She was the best part of our overnight stay."
The price is €100
includes taxes & fees
27 Aug - 28 Aug
Americas Best Value Inn Torrington CT
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

Blackberry River Inn

Blackberry River Inn

10/10 Excellent
"A very charming, historic and elegant inn. The service was excellent."
Mickey 1-night trip
Posted 2 days ago
Blackberry River Inn

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.