Book Hotels in Winchester, CT

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
Jul 23 - Jul 24
Tomorrow
Jul 24 - Jul 25
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

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
$350 nightly
The price is $400 total per night from Jul 27 to Jul 28
$400 total
Jul 27 - Jul 28
Total includes 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 ...
"Love the coffee machine! Love the staff! Loved my stay!"

Reviewed on Jul 13, 2025

Delamar West Hartford
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

3 out of 5
90 CENTURY DRIVE, Bristol, CT
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $175 total per night from Jul 31 to Aug 1
$175 total
Jul 31 - Aug 1
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the hot tub and free perks like continental breakfast and free self parking. A coffee ...
"Our room was spacious and comfortable. Staff was very friendly."

Reviewed on Jul 22, 2025

Home2 Suites by Hilton Bristol
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
$269 nightly
The price is $309 total per night from Jul 27 to Jul 28
$309 total
Jul 27 - Jul 28
Total includes 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 ...
"Excellent"

Reviewed on Jul 10, 2025

Sheraton Hartford Hotel at Bradley Airport
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
$143 nightly
The price is $165 total per night from Aug 14 to Aug 15
$165 total
Aug 14 - Aug 15
Total includes 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. ...
"The digital check in does not work. We did the digital check in on the app and were still asked to visit the front desk for ID. Then the front desk asked for a credit card for the room incidentals when I already inputed this information in the app. Frustrating! The digital key never worked but the ..."

Reviewed on Jul 19, 2025

Hampton Inn & Suites Hartford/Farmington
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave, Farmington, CT
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $149 total per night from Aug 10 to Aug 11
$149 total
Aug 10 - Aug 11
Total includes 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 ...
"The best"

Reviewed on Jul 19, 2025

The Farmington Inn & Suites
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

2.5 out of 5
400 New Britain Ave, Plainville, CT
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $110 total per night from Aug 10 to Aug 11
$110 total
Aug 10 - Aug 11
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
"Staff was amazing"

Reviewed on Jul 20, 2025

Fairfield Inn & Suites by Marriott Plainville
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
$144 nightly
The price is $165 total per night from Aug 10 to Aug 11
$165 total
Aug 10 - Aug 11
Total includes 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. ...
"Clean and quiet. Good breakfast. Pool was nice."

Reviewed on Jul 4, 2025

Homewood 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
$174 nightly
The price is $200 total per night from Jul 29 to Jul 30
$200 total
Jul 29 - Jul 30
Total includes 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 ...
"It was perfect for what we needed- we stayed for one night in the motel section during camp visiting day."

Reviewed on Jul 20, 2025

Avon 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
$123 nightly
The price is $141 total per night from Aug 10 to Aug 11
$141 total
Aug 10 - Aug 11
Total includes 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 ...
"I enjoyed my stay. It was a little home away from home."

Reviewed on Jul 9, 2025

Extended 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 $110. 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 674 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

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

5 out of 5
Posted 21 hours ago
Travelocity Verified Review
"Great spot! We hit Lake Compounce and then the pool at the hotel. I will stay again."
A verified traveler stayed at DoubleTree by Hilton Hotel Bristol, Connecticut
DoubleTree by Hilton Hotel Bristol, Connecticut
Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity