Hotels in Winchester

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This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

Where to stay in Winchester?

Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (112 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 $140
$155 total
includes taxes & fees
Jul 1 - Jul 2
Truman Gillet House Bed & Breakfast
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (91 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 $130
$150 total
includes taxes & fees
Jul 1 - Jul 2
Hitching Post Country Motel
Double Room, Smoking | Iron/ironing board, free WiFi, bed sheets

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.8 out of 10, Good, (196 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 $89
$102 total
includes taxes & fees
Jul 1 - Jul 2
PLYMOUTH MOTOR LODGE
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (238 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 $168
$193 total
includes taxes & fees
Jul 26 - Jul 27
Home2 Suites by Hilton Bristol
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 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 $174
$194 total
includes taxes & fees
Jul 7 - Jul 8
Wilder House Berkshires
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,001 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 $129
$166 total
includes taxes & fees
Jul 1 - Jul 2
The Farmington Inn & Suites
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (427 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 $105
$121 total
includes taxes & fees
Jul 5 - Jul 6
Locust Tree Bed and Breakfast LLC
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (190 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 $164
$189 total
includes taxes & fees
Jul 1 - Jul 2
Blackberry River Inn
Desk, free cribs/infant beds, rollaway beds, free WiFi

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,003 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 $95
$109 total
includes taxes & fees
Jul 5 - Jul 6
Days Inn by Wyndham Torrington
Garden

Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (8 reviews)
The price is $137
$215 total
includes taxes & fees
Jul 19 - Jul 20
Sunny Peace Homestay
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.6 out of 10, Excellent, (30 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 $279
$316 total
includes taxes & fees
Jul 1 - Jul 2
The Millerton Inn
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.6 out of 10, Exceptional, (71 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 $245
$282 total
includes taxes & fees
Jul 20 - Jul 21
The Abner Hotel
Desk, iron/ironing board, free WiFi, bed sheets

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very Good, (1,000 reviews)
Discover a tranquil haven near Batterson Park Pond where restful nights await. This Farmington hotel offers free WiFi, parking, and daily on-the-go breakfast. Business travelers appreciate the convenient location and exceptionally helpful staff.
The price is $105
$121 total
includes taxes & fees
Jul 12 - Jul 13
Extended Stay America Suites Hartford Farmington
Bar (on property)

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,004 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 $246
$283 total
includes taxes & fees
Jul 6 - Jul 7
Sheraton Hartford Hotel at Bradley Airport
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,003 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 $144
$166 total
includes taxes & fees
Jul 20 - Jul 21
Hampton Inn & Suites Hartford/Farmington
Free daily continental breakfast

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 $217
$250 total
includes taxes & fees
Jul 1 - Jul 2
Cornwall Inn and Lodge
Banquet hall

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,010 reviews)
The price is $139
$182 total
includes taxes & fees
Jul 1 - Jul 2
Avon Old Farms Hotel
Exterior

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very Good, (1,004 reviews)
Discover a peaceful haven minutes from Hartford with convenient highway access. This hotel offers an indoor pool, fitness center, and restaurant, plus complimentary breakfast, WiFi, and parking. Clean rooms with washers/dryers create a comfortable extended stay.
The price is $147
$169 total
includes taxes & fees
Jul 2 - Jul 3
Homewood Suites by Hilton Hartford-Farmington
Library

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,000 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 $243
$279 total
includes taxes & fees
Jul 8 - Jul 9
The Litchfield Inn
Lobby lounge

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.4 out of 10, Very Good, (994 reviews)
This quiet hotel offers free breakfast, WiFi and parking just minutes from Crescent Lake. The indoor pool provides year-round relaxation, while the helpful staff ensures a seamless stay for business travelers near Relic Brewing Company.
The price is $131
$151 total
includes taxes & fees
Jul 12 - Jul 13
Fairfield Inn & Suites by Marriott Plainville
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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Top landmarks in Winchester

Highland Lake

Highland Lake is 2.6 mi (4.3 km) from central Winchester, why not stop by during your stay.
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Check out reviews of Winchester hotels guests love

Avon Old Farms Hotel

Avon Old Farms Hotel

8/10 Good
"The place was great. The mattress needs a little help."
Virginia 3-night trip
Posted 16 hours ago
Avon Old Farms Hotel

Frequently asked questions

What hotels do travelers recommend in Winchester?
Guests like Americas Best Value Inn Torrington CT and Days Inn by Wyndham Torrington.
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.