Hotels in Winchester
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Where to stay in Winchester?
Americas Best Value Inn Torrington CT
Americas Best Value Inn Torrington CTTorrington
5.6 out of 10, (784 reviews)
- Relax in the quaint town of Torrington with easy access to hiking trails.
The price is $87
$100 total
includes taxes & fees
Feb 1 - Feb 2
Days Inn by Wyndham Torrington
Days Inn by Wyndham TorringtonTorrington
7.4 out of 10, Good, (1,002 reviews)
- Unwind in Torrington with fitness center access and complimentary breakfast.
The price is $84
$97 total
includes taxes & fees
Feb 2 - Feb 3
Blackberry River Inn
Blackberry River InnNorfolk
9.4 out of 10, Exceptional, (167 reviews)
- Relax at this historic B&B in scenic Norfolk, surrounded by nature's tranquility.
The price is $164
$189 total
includes taxes & fees
Feb 2 - Feb 3
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLCEast Canaan
9.0 out of 10, Wonderful, (414 reviews)
- Experience the charm of East Canaan at this bed and breakfast with countryside views.
The price is $105
$121 total
includes taxes & fees
Feb 1 - Feb 2
The Abner Hotel
The Abner HotelLitchfield Historic District
9.2 out of 10, Wonderful, (48 reviews)
- Wake up to historic charm at this Litchfield hotel with a welcoming rooftop terrace.
The price is $217
$250 total
includes taxes & fees
Feb 22 - Feb 23
The Litchfield Inn
The Litchfield InnLitchfield
9.0 out of 10, Wonderful, (970 reviews)
- Rural charm and spa offerings await at this peaceful Connecticut retreat.
The price is $234
$269 total
includes taxes & fees
Feb 24 - Feb 25
Truman Gillet House Bed & Breakfast
Truman Gillet House Bed & BreakfastGranby
9.6 out of 10, Exceptional, (104 reviews)
- Quaint Connecticut bed and breakfast offers hiking trails and complimentary full breakfast.
The price is $140
$155 total
includes taxes & fees
Feb 1 - Feb 2
Gedney Farm
Gedney FarmGreat Barrington
9.2 out of 10, Wonderful, (135 reviews)
- Rustic farm hotel in the Berkshires with on-site dining and peaceful gardens.
The price is $206
$226 total
includes taxes & fees
Feb 11 - Feb 12
Hitching Post Country Motel
Hitching Post Country MotelCornwall Bridge
6.6 out of 10, (81 reviews)
- Wake up to New England charm in this quaint motel set near hiking trails and parks.
The price is $130
$150 total
includes taxes & fees
Feb 1 - Feb 2
Residence Inn by Marriott Hartford Avon
Residence Inn by Marriott Hartford AvonAvon
8.8 out of 10, Excellent, (423 reviews)
- Relax in Avon with easy access to Hartford's top attractions and golf courses.
The price is $127
$146 total
includes taxes & fees
Feb 8 - Feb 9
Interlaken Inn & Resort
Interlaken Inn & ResortLakeville
8.2 out of 10, Very Good, (276 reviews)
- Enjoy a serene getaway at this Lakeville golf-adjacent resort with a full-service spa.
The price is $179
$206 total
includes taxes & fees
Feb 5 - Feb 6
Wilder House Berkshires
Wilder House BerkshiresSheffield
9.8 out of 10, Exceptional, (43 reviews)
- Stay at a charming Sheffield B&B with a convenient weekend breakfast service.
The price is $165
$184 total
includes taxes & fees
Feb 3 - Feb 4
The Old Inn On The Green
The Old Inn On The GreenGreat Barrington
9.2 out of 10, Wonderful, (90 reviews)
- Seasonal escape in historic Great Barrington with outdoor pool and fine dining.
The price is $305
$368 total
includes taxes & fees
Feb 1 - Feb 2
Avon Old Farms Hotel
Avon Old Farms HotelAvon
8.4 out of 10, Very Good, (1,001 reviews)
The price is $109
$147 total
includes taxes & fees
Feb 2 - Feb 3
Simsbury 1820 House
Simsbury 1820 HouseSimsbury Center
9.2 out of 10, Wonderful, (1,000 reviews)
- Peaceful retreat in Simsbury offers historic charm and serene pool escape.
The price is $159
$200 total
includes taxes & fees
Feb 1 - Feb 2
PLYMOUTH MOTOR LODGE
PLYMOUTH MOTOR LODGETerryville
7.6 out of 10, Good, (180 reviews)
- Experience Terryville comfort with free WiFi and parking at this convenient lodge.
The price is $80
$92 total
includes taxes & fees
Feb 1 - Feb 2
The White Hart
The White HartSalisbury
9.8 out of 10, Exceptional, (146 reviews)
- Restored 17th-century inn with garden views, near Mount Frissell.
The price is $261
$301 total
includes taxes & fees
Feb 1 - Feb 2
Cornwall Inn and Lodge
Cornwall Inn and LodgeCornwall Bridge
9.2 out of 10, Wonderful, (156 reviews)
- Cozy Connecticut inn with complimentary breakfast and a seasonal pool to enjoy.
The price is $212
$243 total
includes taxes & fees
Feb 1 - Feb 2
Simsbury Inn
Simsbury InnSimsbury Center
9.2 out of 10, Wonderful, (286 reviews)
- Modern Connecticut hotel with resort-style amenities in scenic Weatogue area.
The price is $249
$308 total
includes taxes & fees
Feb 1 - Feb 2
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.
Go beyond your typical stay in Winchester
Pet friendly
Top landmarks in Winchester
Check out reviews of Winchester hotels guests love
Sheraton Hartford Hotel at Bradley Airport
10/10 Excellent
