Hotels in Winchester

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Check prices for these dates

Tonight
Mar 28 - Mar 29
Tomorrow
Mar 29 - Mar 30
Next weekend
Apr 3 - Apr 5
In two weeks
Apr 10 - Apr 12

Where to stay in Winchester?

Exterior
Sheraton Hartford Hotel at Bradley Airport
Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Unwind steps from arrivals with quick fitness access and welcoming service.
The price is $220
$253 total
includes taxes & fees
Apr 2 - Apr 3
Sheraton Hartford Hotel at Bradley Airport
Lunch and dinner served
Delamar West Hartford
Delamar West Hartford
4.0 star property
West Hartford
9.8 out of 10, Exceptional, (1,003 reviews)
  • cleanliness
    Experience upscale comfort near Blue Back Square with a rejuvenating spa retreat.
The price is $377
$448 total
includes taxes & fees
Apr 5 - Apr 6
Delamar West Hartford
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, (1,001 reviews)
  • cleanliness
    Peaceful hotel in Farmington with free perks, parking, and helpful staff support.
The price is $108
$124 total
includes taxes & fees
Mar 30 - Mar 31
Extended Stay America Suites Hartford Farmington
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, (1,003 reviews)
  • cleanliness
    Serene retreat near Hartford with a tranquil pool and complimentary perks.
The price is $144
$165 total
includes taxes & fees
Apr 3 - Apr 4
Homewood Suites by Hilton Hartford-Farmington
Exterior
Hampton Inn & Suites Hartford/Farmington
Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Swim near Hartford with a hot tub to end your perfect business day.
The price is $122
$141 total
includes taxes & fees
Apr 11 - Apr 12
Hampton Inn & Suites Hartford/Farmington
Lobby
Fairfield Inn & Suites by Marriott Plainville
Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (952 reviews)
  • cleanliness
    Modern comfort in the heart of Plainville with a serene 24-hour fitness center.
The price is $101
$116 total
includes taxes & fees
Apr 10 - Apr 11
Fairfield Inn & Suites by Marriott Plainville
Staircase
The Farmington Inn & Suites
The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Quiet retreat near Hartford with Victorian charm and a welcoming café.
The price is $127
$164 total
includes taxes & fees
Apr 5 - Apr 6
The Farmington Inn & Suites
Interior
Avon Old Farms Hotel
Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,003 reviews)
The price is $135
$178 total
includes taxes & fees
Apr 1 - Apr 2
Avon Old Farms Hotel
Reception
Simsbury 1820 House
Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Peaceful retreat in Simsbury offers historic charm and serene pool escape.
The price is $159
$200 total
includes taxes & fees
Mar 30 - Mar 31
Simsbury 1820 House
Indoor spa tub
Simsbury Inn
Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (290 reviews)
  • cleanliness
    Modern Connecticut hotel with resort-style amenities in scenic Weatogue area.
The price is $237
$294 total
includes taxes & fees
Mar 30 - Mar 31
Simsbury Inn
BBQ/picnic area
Residence Inn by Marriott Hartford Avon
Residence Inn by Marriott Hartford Avon
3.0 star property
Avon
8.8 out of 10, Excellent, (429 reviews)
  • cleanliness
    Relax in Avon with easy access to Hartford's top attractions and golf courses.
The price is $144
$165 total
includes taxes & fees
Apr 4 - Apr 5
Residence Inn by Marriott Hartford Avon
Property entrance
Truman Gillet House Bed & Breakfast
Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (104 reviews)
  • cleanliness
    Quaint Connecticut bed and breakfast offers hiking trails and complimentary full breakfast.
The price is $140
$155 total
includes taxes & fees
Mar 30 - Mar 31
Truman Gillet House Bed & Breakfast
Terrace/patio
DoubleTree by Hilton Hotel Bristol, Connecticut
DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Experience quiet lodging with indoor pool and friendly staff in Bristol, Connecticut.
The price is $155
$178 total
includes taxes & fees
Apr 5 - Apr 6
DoubleTree by Hilton Hotel Bristol, Connecticut
Terrace/patio
Home2 Suites by Hilton Bristol
Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (204 reviews)
  • cleanliness
    Home2 Suites offers both comfort and convenience in Bristol with free breakfast.
The price is $134
$154 total
includes taxes & fees
Apr 16 - Apr 17
Home2 Suites by Hilton Bristol
Interior
PLYMOUTH MOTOR LODGE
PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (184 reviews)
  • cleanliness
    Experience Terryville comfort with free WiFi and parking at this convenient lodge.
The price is $80
$92 total
includes taxes & fees
Mar 30 - Mar 31
PLYMOUTH MOTOR LODGE
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, (1,000 reviews)
  • cleanliness
    Unwind in Torrington with fitness center access and complimentary breakfast.
The price is $84
$97 total
includes taxes & fees
Apr 1 - Apr 2
Days Inn by Wyndham Torrington
Premium bedding, down comforters, Select Comfort beds, in-room safe
Americas Best Value Inn Torrington CT
Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (787 reviews)
  • cleanliness
    Relax in the quaint town of Torrington with easy access to hiking trails.
The price is $93
$108 total
includes taxes & fees
Apr 1 - Apr 2
Americas Best Value Inn Torrington CT
Restaurant
The Abner Hotel
The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (57 reviews)
  • cleanliness
    Wake up to historic charm at this Litchfield hotel with a welcoming rooftop terrace.
The price is $308
$354 total
includes taxes & fees
Apr 20 - Apr 21
The Abner Hotel
Library
The Litchfield Inn
The Litchfield Inn
4.0 star property
Litchfield
9.0 out of 10, Wonderful, (977 reviews)
  • cleanliness
    Rural charm and spa offerings await at this peaceful Connecticut retreat.
The price is $269
$309 total
includes taxes & fees
Apr 8 - Apr 9
The Litchfield Inn
Porch
Mayflower Inn & Spa, Auberge Collection
Mayflower Inn & Spa, Auberge Collection
5.0 star property
Washington
9.4 out of 10, Exceptional, (59 reviews)
  • cleanliness
    Escape to Washington's countryside and rejuvenate at this luxurious spa retreat.
The price is $655
$811 total
includes taxes & fees
Mar 31 - Apr 1
Mayflower Inn & Spa, Auberge Collection
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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Northwestern Connecticut Community College

If you'd like to get a taste of Winchester student life, check out Northwestern Connecticut Community College, in the heart of the town.
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Check out reviews of Winchester hotels guests love

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent
"Go local "
marlou 4-night trip
Posted 1 day ago
Homewood Suites by Hilton Hartford-Farmington

Frequently asked questions

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.