Book Hotels in Winchester, CT

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Top Winchester hotels

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Winchester CT
A gym is featured at this vacation home, along with a garden and laundry facilities.
"Pet friendly beautiful clean house on lake. Host is very easy to work with."

Reviewed on Sep 8, 2026

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Opens in a new windowFamily-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR
Delamar West Hartford

Delamar West Hartford

4 out of 5
1 Memorial Road West Hartford CT
$355 nightly
The price is $405 total per night from Nov 1 to Nov 2
$405 total
Nov 1 - Nov 2
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 ...
"The staff was amazing. Super helpful and kind. The room was one of the most beautiful and elegant places we’ve stayed at and the hotel amenities, and restaurant was just something I’ll never forget. Thank you for this experience!"

Reviewed on Oct 5, 2026

Opens in a new windowDelamar West Hartford
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

5 out of 5
118 Woodbury Rd. Washington CT
$1,419 nightly
The price is $1,632 total per night from Nov 2 to Nov 3
$1,632 total
Nov 2 - Nov 3
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Enjoy the gym and perks like free valet parking and free WiFi. You'll ...
"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."

Reviewed on Sep 13, 2026

Opens in a new windowMayflower Inn & Spa, Auberge Collection
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted CT
$210 nightly
The price is $238 total per night from Oct 8 to Oct 9
$238 total
Oct 8 - Oct 9
Total with taxes and fees
A hot tub is featured at this apartment, along with a garden.
Opens in a new windowEnjoy a restful stay with fast internet, smart TV and the company of your pet.
Waterfront House & Guest House Available in Winchester, CT!

Waterfront House & Guest House Available in Winchester, CT!

Winchester CT
This vacation home features laundry facilities.
Get rates
Opens in a new window Waterfront House & Guest House Available in Winchester, CT!
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
$254 nightly
The price is $292 total per night from Oct 31 to Nov 1
$292 total
Oct 31 - Nov 1
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 ...
Opens in a new windowSheraton Hartford Hotel at Bradley Airport
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $149 total per night from Nov 2 to Nov 3
$149 total
Nov 2 - Nov 3
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 ...
Opens in a new windowThe Farmington Inn & Suites
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3 out of 5
2 Farm Glen Blvd Farmington CT
$169 nightly
The price is $195 total per night from Oct 18 to Oct 19
$195 total
Oct 18 - Oct 19
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. ...
Opens in a new windowHomewood Suites by Hilton Hartford-Farmington
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
$163 nightly
The price is $188 total per night from Oct 15 to Oct 16
$188 total
Oct 15 - Oct 16
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 ...
Opens in a new windowDoubleTree by Hilton Hotel Bristol, Connecticut
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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 $149. 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 704 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

Delamar West Hartford

Delamar West Hartford

5 out of 5
Posted 15 hours ago
Travelocity Verified Review
"The staff was amazing. Super helpful and kind. The room was one of the most beautiful and elegant places we’ve stayed at and the hotel amenities, and restaurant was just something I’ll never forget. Thank you for this experience!"
A verified traveler stayed at Delamar West Hartford
Delamar West Hartford

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