Hotels in Winchester

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Where to stay in Winchester?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Winchester on Hotels.com. These Winchester hotels consistently deliver on comfort, location and traveler experience. Last updated on .

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (111 reviews)
Discover historic charm at this B&B near McLean Game Refuge. Wake up to a daily full breakfast before exploring hiking trails. Free WiFi and parking add convenience while Old New-Gate Prison is just a short drive away.
The price is CNY948
CNY1,052 total
includes taxes & fees
Jun 23 - Jun 24
Truman Gillet House Bed & Breakfast

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (186 reviews)
Unwind in this peaceful country retreat with a seasonal outdoor pool and complimentary gourmet breakfast. Located near Haystack Mountain State Park, the inn offers free WiFi and parking while helpful staff ensure a memorable stay in Norfolk's quiet surroundings.
The price is CNY1,054
CNY1,212 total
includes taxes & fees
Jun 21 - Jun 22
Blackberry River Inn

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (88 reviews)
This countryside motel offers free WiFi and parking with 24-hour front desk assistance. Located near Housatonic Meadows State Park and Clarke Outdoors, it's perfect for outdoor enthusiasts looking to explore hiking trails and snowboarding venues.
The price is CNY880
CNY1,012 total
includes taxes & fees
Jun 21 - Jun 22
Hitching Post Country Motel

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,001 reviews)
Located near Hotchkiss-Fyler House Museum and Warner Theater, this motel offers free WiFi and parking. Enjoy the on-site fitness center or venture to nearby downhill skiing. Clean rooms provide a comfortable base while the exceptionally helpful staff ensures a pleasant stay.
The price is CNY650
CNY748 total
includes taxes & fees
Jun 29 - Jun 30
Days Inn by Wyndham Torrington

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (54 reviews)
Escape to the Berkshires in this inviting Sheffield accommodation with complimentary WiFi and parking. Start your day with cooked-to-order weekend breakfast before exploring nearby Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary.
The price is CNY1,305
CNY1,457 total
includes taxes & fees
Jun 22 - Jun 23
Wilder House Berkshires

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,003 reviews)
Connected to Bradley Intl. Airport, this Windsor Locks hotel offers a 24-hour fitness center and American cuisine at Concorde Restaurant. Quiet rooms provide a peaceful sleep near the Connecticut Fallen Firefighters Memorial and New England Air Museum.
The price is CNY1,509
CNY1,736 total
includes taxes & fees
Jul 2 - Jul 3
Sheraton Hartford Hotel at Bradley Airport

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (195 reviews)
This inviting hotel offers convenient perks including complimentary WiFi and parking. Located near Witch's Dungeon Classic Movie Museum and Rockwell Park, you'll enjoy comfortable accommodations with 24-hour front desk service for a hassle-free stay.
The price is CNY602
CNY693 total
includes taxes & fees
Jun 21 - Jun 22
PLYMOUTH MOTOR LODGE

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.6 out of 10, Excellent, (29 reviews)
Relish free breakfast before exploring the Harlem Valley Rail Trail and Yoakum Preserve. This hotel offers complimentary WiFi and parking, with the on-site restaurant serving Mediterranean dishes for lunch and dinner in charming surroundings.
The price is CNY1,700
CNY1,923 total
includes taxes & fees
Jun 21 - Jun 22
The Millerton Inn

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
Escape to this serene Farmington hotel, just 15 minutes from Hartford Convention Center. Start your day with complimentary breakfast at Victoria's Café before exploring nearby Miss Porter's School. The health club, room service, and exceptionally helpful staff ensure a comfortable stay.
The price is CNY929
CNY1,185 total
includes taxes & fees
Jun 21 - Jun 22
The Farmington Inn & Suites

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (165 reviews)
This charming Cornwall Bridge lodge offers free WiFi, parking, and daily continental breakfast. Swim in the seasonal outdoor pool or unwind on the terrace surrounded by gardens. Kent Falls State Park and the Appalachian Trail provide nearby adventure opportunities.
The price is CNY1,471
CNY1,692 total
includes taxes & fees
Jun 21 - Jun 22
Cornwall Inn and Lodge

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (230 reviews)
Wake up to a complimentary breakfast at this Bristol hotel before exploring nearby Pine Lake Park. Unwind in the hot tub after a workout in the 24-hour fitness center, or enjoy a drink at the bar. In-room refrigerators and microwaves add convenience to your stay.
The price is CNY1,022
CNY1,175 total
includes taxes & fees
Jul 2 - Jul 3
Home2 Suites by Hilton Bristol

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (423 reviews)
Wake up to a complimentary full breakfast at this cozy East Canaan B&B. Located near Land of Nod Vineyard and Winery, the inn offers free parking and daily housekeeping. Guests consistently praise the helpful staff for making stays memorable.
The price is CNY711
CNY817 total
includes taxes & fees
Jun 21 - Jun 22
Locust Tree Bed and Breakfast LLC

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,004 reviews)
Located in Farmington, this hotel offers free WiFi and parking, plus an indoor pool and hot tub for relaxation. Enjoy a complimentary breakfast before exploring nearby Hill-Stead Museum, or maintain your routine at the 24-hour fitness center.
The price is CNY827
CNY951 total
includes taxes & fees
Jun 29 - Jun 30
Hampton Inn & Suites Hartford/Farmington

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (68 reviews)
Savor free breakfast at this inviting 3-star hotel before exploring nearby Litchfield Town Green. Return for evening drinks at the bar while taking in views from the rooftop terrace. Free WiFi and parking make your Connecticut getaway seamless.
The price is CNY1,657
CNY1,906 total
includes taxes & fees
Jul 12 - Jul 13
The Abner Hotel

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (999 reviews)
Steps from White Memorial Conservation Center and Mount Tom State Park, this Litchfield Inn features a full-service spa for rejuvenating treatments. Enjoy complimentary breakfast, WiFi, and parking while the attentive staff ensures a memorable stay.
The price is CNY1,840
CNY2,115 total
includes taxes & fees
Jun 21 - Jun 22
The Litchfield Inn

Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (299 reviews)
Discover classic comforts at this charming Weatogue retreat featuring 3 restaurants including local cuisine at Evergreens. An indoor pool, fitness center, and complimentary breakfast enhance your stay near Rosedale Farms and Stratton Brook State Park.
The price is CNY1,956
CNY2,397 total
includes taxes & fees
Jun 21 - Jun 22
Simsbury Inn

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,000 reviews)
Immerse yourself in the rich history of this Simsbury B&B, where an indoor pool and fitness center await. Enjoy complimentary breakfast, WiFi, and bike rentals near Performing Arts Center, with 2 bars and a restaurant for evening relaxation.
The price is CNY1,618
CNY1,977 total
includes taxes & fees
Jun 21 - Jun 22
Simsbury 1820 House

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (137 reviews)
Unwind at this charming Great Barrington retreat featuring complimentary breakfast, WiFi, and parking. The hotel offers a restaurant, welcoming bar, and tranquil outdoor spaces near Questing and New Marlborough Town Library.
The price is CNY1,255
CNY1,377 total
includes taxes & fees
Jun 24 - Jun 25
Gedney Farm

Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (139 reviews)
Wake up to complimentary breakfast at this cozy B&B, then explore nearby trails by foot or on free rental bikes. Infinity Music Hall and Norfolk Historical Museum are close, while perks like free WiFi, parking, and a garden enhance your countryside retreat.
Manor House Inn

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (151 reviews)
A charming stay in Salisbury at this historic hotel with a welcoming bar and café. Unwind in the peaceful garden or relax on the terrace after exploring nearby Mount Frissell and Hanging Rock Park. Free breakfast, WiFi, and parking enhance your visit.
The price is CNY2,324
CNY2,672 total
includes taxes & fees
Jun 21 - Jun 22
The White Hart
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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Frequently asked questions

How much does a hotel room cost in Winchester?
You can discover great hotels in Winchester from CNY693 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Winchester that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.
How can I find deals and earn rewards at Winchester hotels?
Discover great deals on Winchester hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. And make sure to check out our last-minute deals on Winchester hotels.
Can I book Winchester hotels with free cancellation?
To book a refundable Winchester hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some popular hotels in central Winchester?
If you're looking for hotels in central Winchester, check out Rock Hall Luxe Lodging. Travelers love Rock Hall Luxe Lodging for its location, as well as the outdoor pool, hot tub and outdoor tennis court this bed & breakfast offers.
What hotels do travelers recommend in Winchester?
Can I book refundable accommodations in Winchester?
If you want the flexibility to change your plans to Winchester, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Winchester if I want a vacation rental instead of a hotel?
If you're looking for a good alternative to a hotel, browse our selection of 8 vacation homes. In addition, you can choose from 5 apartments.
What will the weather in Winchester be like during my vacation?
July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 30°F. July and October are the months with the most rain.
Why should I book my Winchester hotel with Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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