Book Hotels in Winchester, CT

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Tonight
Nov 28 - Nov 29
Tomorrow
Nov 29 - Nov 30
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Winchester hotels

Delamar West Hartford

Delamar West Hartford

4 out of 5
1 Memorial Road West Hartford CT
Fully refundableReserve now, pay when you stay
$311 nightly
The price is $356 total per night from Nov 29 to Nov 30
$356 total
Nov 29 - Nov 30
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free ...
Wonderful as always!

Reviewed on Nov 18, 2025

Opens in a new windowDelamar West Hartford
Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St Simsbury CT
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $200 total per night from Nov 30 to Dec 1
$200 total
Nov 30 - Dec 1
Total with taxes and fees
The bed & breakfast's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center ...
Room was great

Reviewed on Nov 25, 2025

Opens in a new windowSimsbury 1820 House
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport Windsor Locks CT
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $263 total per night from Dec 5 to Dec 6
$263 total
Dec 5 - Dec 6
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
The convenience of staying at a hotel attached to the airport was unmatched. We had the room for a little under 12 hours and it was worth every penny to not have to rush at 4AM to get to TSA on the weekend before Thanksgiving.

Reviewed on Nov 24, 2025

Opens in a new windowSheraton Hartford Hotel at Bradley Airport
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

4 out of 5
42 Century Dr Bristol CT
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $169 total per night from Dec 18 to Dec 19
$169 total
Dec 18 - Dec 19
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free valet parking and free WiFi. Enjoy the hot tub ...
All good

Reviewed on Nov 23, 2025

Opens in a new windowDoubleTree by Hilton Hotel Bristol, Connecticut
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $172 total per night from Dec 4 to Dec 5
$172 total
Dec 4 - Dec 5
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the 24-hour business center. Enjoy the free continental breakfast ...
Staff

Reviewed on Nov 25, 2025

Opens in a new windowThe Farmington Inn & Suites
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

2.5 out of 5
301 Colt Hwy Farmington CT
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $124 total per night from Dec 20 to Dec 21
$124 total
Dec 20 - Dec 21
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. ...
Excellent

Reviewed on Nov 23, 2025

Opens in a new windowHampton Inn & Suites Hartford/Farmington
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3 out of 5
2 Farm Glen Blvd Farmington CT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $132 total per night from Dec 21 to Dec 22
$132 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
Very good location for us. Room was very spacious with living, dining and sleeping areas.

Reviewed on Oct 28, 2025

Opens in a new windowHomewood Suites by Hilton Hartford-Farmington
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd Avon CT
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $150 total per night from Dec 1 to Dec 2
$150 total
Dec 1 - Dec 2
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and WiFi in public ...
Beautiful room and property. Had a wonderful time! Definitely will stay again.

Reviewed on Nov 25, 2025

Opens in a new windowAvon Old Farms Hotel
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $109 total per night from Dec 5 to Dec 6
$109 total
Dec 5 - Dec 6
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A safe deposit box ...
Large room

Reviewed on Nov 26, 2025

Opens in a new windowExtended Stay America Suites Hartford Farmington
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
Take some of the hassles out of traveling with youngsters by booking a family-friendly Winchester hotel. From thoughtful amenities to additional services, these properties feature perks that'll make your visit run smoothly: You'll be well taken care of at Newly Renovated Family House On Highland Lake with Dock. It comes with a nearby beach, animal viewing activities and a knack for making families feel welcome. Alternatively, spend your Winchester trip at The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock. Make the most of a playground, animal viewing activities and more here.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is $109. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 681 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during June, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers

Avon Old Farms Hotel

Avon Old Farms Hotel

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Beautiful room and property. Had a wonderful time! Definitely will stay again. "
A verified traveler stayed at Avon Old Farms Hotel
Avon Old Farms Hotel

Explore More Ways to Travel with Travelocity