Hotels in Winchester

Where to?

Dates

February 2026

March 2026

I'm traveling for business

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Where to stay in Winchester?

Premium bedding, down comforters, Select Comfort beds, in-room safe

Americas Best Value Inn Torrington CT

Torrington

Relax in the quaint town of Torrington with easy access to hiking trails.

CNY693 total

includes taxes & fees

Feb 5 - Feb 6

Desk, free cribs/infant beds, rollaway beds, free WiFi

Days Inn by Wyndham Torrington

Torrington

Unwind in Torrington with fitness center access and complimentary breakfast.

CNY673 total

includes taxes & fees

Feb 5 - Feb 6

Blackberry River Inn

Norfolk

Relax at this historic B&B in scenic Norfolk, surrounded by nature's tranquility.

CNY1,315 total

includes taxes & fees

Feb 2 - Feb 3

Locust Tree Bed and Breakfast LLC

East Canaan

Experience the charm of East Canaan at this bed and breakfast with countryside views.

CNY839 total

includes taxes & fees

Feb 6 - Feb 7

The Abner Hotel

Litchfield Historic District

Wake up to historic charm at this Litchfield hotel with a welcoming rooftop terrace.

The Litchfield Inn

Litchfield

Rural charm and spa offerings await at this peaceful Connecticut retreat.

CNY1,869 total

includes taxes & fees

Feb 24 - Feb 25

Truman Gillet House Bed & Breakfast

Granby

Quaint Connecticut bed and breakfast offers hiking trails and complimentary full breakfast.

CNY1,080 total

includes taxes & fees

Feb 5 - Feb 6

Gedney Farm

Great Barrington

Rustic farm hotel in the Berkshires with on-site dining and peaceful gardens.

CNY1,415 total

includes taxes & fees

Feb 11 - Feb 12

Hitching Post Country Motel

Cornwall Bridge

Wake up to New England charm in this quaint motel set near hiking trails and parks.

CNY1,039 total

includes taxes & fees

Feb 10 - Feb 11

Residence Inn by Marriott Hartford Avon

Avon

Relax in Avon with easy access to Hartford's top attractions and golf courses.

CNY1,013 total

includes taxes & fees

Feb 8 - Feb 9

The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

Salisbury

Countryside retreat with snowboarding nearby and garden views to complement stay.

CNY3,950 total

includes taxes & fees

Feb 2 - Feb 3

Interlaken Inn & Resort

Lakeville

Enjoy a serene getaway at this Lakeville golf-adjacent resort with a full-service spa.

CNY1,432 total

includes taxes & fees

Feb 6 - Feb 7

Wilder House Berkshires

Sheffield

Stay at a charming Sheffield B&B with a convenient weekend breakfast service.

Breakfast, lunch, dinner served; American cuisine

The Old Inn On The Green

Great Barrington

Seasonal escape in historic Great Barrington with outdoor pool and fine dining.

CNY2,559 total

includes taxes & fees

Feb 4 - Feb 5

Avon Old Farms Hotel

Avon

CNY1,023 total

includes taxes & fees

Feb 6 - Feb 7

Simsbury 1820 House

Simsbury Center

Peaceful retreat in Simsbury offers historic charm and serene pool escape.

CNY1,391 total

includes taxes & fees

Feb 10 - Feb 11

PLYMOUTH MOTOR LODGE

Terryville

Experience Terryville comfort with free WiFi and parking at this convenient lodge.

CNY640 total

includes taxes & fees

Feb 1 - Feb 2

John Harney Suite | Minibar, desk, iron/ironing board, free WiFi

The White Hart

Salisbury

Restored 17th-century inn with garden views, near Mount Frissell.

CNY2,092 total

includes taxes & fees

Feb 1 - Feb 2

Cornwall Inn and Lodge

Cornwall Bridge

Cozy Connecticut inn with complimentary breakfast and a seasonal pool to enjoy.

CNY1,692 total

includes taxes & fees

Feb 10 - Feb 11

Simsbury Inn

Simsbury Center

Modern Connecticut hotel with resort-style amenities in scenic Weatogue area.

CNY2,144 total

includes taxes & fees

Feb 1 - Feb 2

View all properties

Go beyond your typical stay in Winchester

Family friendly

Hot tub

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.

See properties

The Marina at Highland Lake

Imagine strolling along The Marina at Highland Lake for some great waterfront pics. It's located 1.8 mi (2.9 km) from central Winchester.

See properties

Check out reviews of Winchester hotels guests love

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"I love this Wonderful Location and the breakfast is astounding!"

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent

"Check in was seamless. We arrived in our room late and were happy with the accommodations. The room was neat, the floor was quiet and we were able to quickly warm up from the frigid temps as soon as we turned the heat on. One thing I will say is the water in the shower got chilly a little too quickly and it didn’t warm up. I loved the availability of coffee at any time and the staff was really attentive. We would definitely stay here again."

Frequently asked questions

How much does a hotel room cost in Winchester?

You can discover great hotels in Winchester from CNY640 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?

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 7 vacation homes. In addition, you can choose from 6 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.

Keep exploring

Book Hotels in Winchester on Hotels.com