Hotels in Winchester

Q: What hotels do travelers recommend in Winchester?

Guests like Days Inn by Wyndham Torrington .

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Dates

April 2026

May 2026

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Where to stay in Winchester?

Sheraton Hartford Hotel at Bradley Airport

Windsor Locks

Unwind steps from arrivals with quick fitness access and welcoming service.

CNY1,680 total

includes taxes & fees

Apr 4 - Apr 5

Delamar West Hartford

West Hartford

Experience upscale comfort near Blue Back Square with a rejuvenating spa retreat.

CNY2,789 total

includes taxes & fees

Apr 5 - Apr 6

Desk, iron/ironing board, free WiFi, bed sheets

Extended Stay America Suites Hartford Farmington

Farmington

Peaceful hotel in Farmington with free perks, parking, and helpful staff support.

CNY812 total

includes taxes & fees

Mar 29 - Mar 30

Homewood Suites by Hilton Hartford-Farmington

Farmington

Serene retreat near Hartford with a tranquil pool and complimentary perks.

CNY1,125 total

includes taxes & fees

Mar 21 - Mar 22

Hampton Inn & Suites Hartford/Farmington

Farmington

Swim near Hartford with a hot tub to end your perfect business day.

CNY975 total

includes taxes & fees

Apr 18 - Apr 19

Fairfield Inn & Suites by Marriott Plainville

Plainville

Modern comfort in the heart of Plainville with a serene 24-hour fitness center.

CNY776 total

includes taxes & fees

Mar 29 - Mar 30

The Farmington Inn & Suites

Farmington

Quiet retreat near Hartford with Victorian charm and a welcoming café.

CNY1,127 total

includes taxes & fees

Mar 19 - Mar 20

Avon Old Farms Hotel

Avon

CNY1,217 total

includes taxes & fees

Mar 31 - Apr 1

Simsbury 1820 House

Simsbury Center

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

CNY1,378 total

includes taxes & fees

Mar 29 - Mar 30

Simsbury Inn

Simsbury Center

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

CNY2,025 total

includes taxes & fees

Mar 29 - Mar 30

Residence Inn by Marriott Hartford Avon

Avon

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

CNY935 total

includes taxes & fees

Mar 29 - Mar 30

Truman Gillet House Bed & Breakfast

Granby

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

CNY1,070 total

includes taxes & fees

Mar 23 - Mar 24

DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

Experience quiet lodging with indoor pool and friendly staff in Bristol, Connecticut.

CNY1,198 total

includes taxes & fees

Mar 29 - Mar 30

Home2 Suites by Hilton Bristol

Bristol

Home2 Suites offers both comfort and convenience in Bristol with free breakfast.

CNY1,030 total

includes taxes & fees

Apr 2 - Apr 3

PLYMOUTH MOTOR LODGE

Terryville

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

CNY633 total

includes taxes & fees

Mar 31 - Apr 1

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.

CNY734 total

includes taxes & fees

Apr 7 - Apr 8

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.

CNY740 total

includes taxes & fees

Apr 1 - Apr 2

The Abner Hotel

Litchfield Historic District

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

CNY2,100 total

includes taxes & fees

Mar 22 - Mar 23

The Litchfield Inn

Litchfield

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

CNY1,960 total

includes taxes & fees

Mar 26 - Mar 27

Mayflower Inn & Spa, Auberge Collection

Washington

Escape to Washington's countryside and rejuvenate at this luxurious spa retreat.

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Go beyond your typical stay in Winchester

Pet friendly

Spa

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

Platt Hill State Park

Platt Hill State Park is 2.4 mi (3.8 km) from central Winchester, why not stop by during your stay.

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Check out reviews of Winchester hotels guests love

Simsbury 1820 House

10/10 Excellent

"Absolutely LOVE this hotel/B&B!!! I have stayed several times, and the staff is always amazing, and the rooms are always very clean. Will definitely be back:-)"

Days Inn by Wyndham Torrington

2/10 Terrible

"Parking lot filthy dirty, alcohol bottles, trash all over. Upon arrival I see 2 guys climbing out window from their room. Back door is never locked, area around it also filthy including hallway inside. NOT at all pet friendly, no where to walk dog All night long people yelling, fighting, etc front desk does nothing. Room (bed area) clean, tub so disgusting I wouldn't go in it."

Home2 Suites by Hilton Bristol

10/10 Excellent

"The room was fantastic - so very comfortable, so spacious, tons of closet, drawer, cabinet and shelf space, a movable computer table, well-stocked kitchen, spacious bath. At breakfast, the apple and orange juices were absolutely delicious. Minor comments: The bath towels could use a little fabric softener, and while breakfast was good, and the pre-made items were abundant and convenient, some were over or under cooked. Surprised they didn't offer a non-stick spray for the waffle makers. "

Frequently asked questions

How much does a hotel room cost in Winchester?

You can discover great hotels in Winchester from CNY633 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 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.

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