Book Cheap Hotels in Winchester

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Check prices in Winchester for tonight, Nov 16 - Nov 17
Nov 16 - Nov 17
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Nov 17 - Nov 18
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Nov 21 - Nov 23

Most frequently booked Winchester hotels

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
Free cancellation
Reserve now, pay when you stay
2.41 km from city centre
The price is CA $113 per night
CA $113
CA $125 total
Nov 23 - Nov 24
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Wiseman Park and Community Park are located nearby.
Pool
Breakfast included
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
Free cancellation
Reserve now, pay when you stay
28.93 km from city centre
The price is CA $191 per night
CA $191
CA $221 total
Nov 29 - Nov 30
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kroger Field and Keeneland Racing Course are located nearby.
Pool
Free airport shuttle
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Free cancellation
Reserve now, pay when you stay
29.79 km from city centre
The price is CA $211 per night
CA $211
CA $270 total
Nov 27 - Nov 28
includes taxes & fees
Stay at this hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Kroger Field and Keeneland Racing Course are located nearby.
Pet-friendly
Free WiFi
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
Free cancellation
Reserve now, pay when you stay
22.14 km from city centre
The price is CA $90 per night
CA $90
CA $104 total
Nov 30 - Dec 1
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kroger Field and Hamburg Place are located nearby.
Breakfast included
Parking included
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
Free cancellation
Reserve now, pay when you stay
29.26 km from city centre
The price is CA $95 per night
CA $95
CA $111 total
Nov 30 - Dec 1
includes taxes & fees
Book a stay at this golf hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kentucky Horse Park and Rupp Arena are located nearby.
Breakfast included
Pet-friendly
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
Free cancellation
Reserve now, pay when you stay
18.22 km from city centre
The price is CA $112 per night
CA $112
CA $130 total
Nov 27 - Nov 28
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lexington Sporting Club Youth Complex and Boone Station State Historic Site are located nearby.
Pool
Breakfast included
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 out of 5
1801 Newtown Pike Lexington KY
Free cancellation
Reserve now, pay when you stay
29.29 km from city centre
The price is CA $134 per night
CA $134
CA $155 total
Nov 30 - Dec 1
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kentucky Horse Park and Kroger Field are located nearby.
Pool
Breakfast included
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street Lexington KY
Free cancellation
Reserve now, pay when you stay
28.83 km from city centre
The price is CA $171 per night
CA $171
CA $199 total
Nov 30 - Dec 1
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kroger Field and Keeneland Racing Course are located nearby.
Pool
Free airport shuttle
Tru by Hilton University Medical Center

Tru by Hilton University Medical Center

2.5 out of 5
535 Waller Avenue Lexington KY
Free cancellation
Reserve now, pay when you stay
30.4 km from city centre
The price is CA $114 per night
CA $114
CA $132 total
Nov 23 - Nov 24
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kroger Field and Keeneland Racing Course are located nearby.
Breakfast included
Pet-friendly
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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.

Top family friendly Winchester hotel deals

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Dr, Winchester, KY
The price is CA $112 per night from Nov 23 to Nov 24
CA $112
CA $123 total
Nov 23 - Nov 24
includes taxes & fees
7/10 Good! (765 reviews)

Top cheap Winchester hotel deals

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Dr, Winchester, KY
The price is CA $112 per night from Nov 23 to Nov 24
CA $112
CA $123 total
Nov 23 - Nov 24
includes taxes & fees
7/10 Good! (765 reviews)

Winchester hotels essential information

Accommodation
1,172 hotels
Lowest Price
CA $96
Highest Price
CA $270
Popular hotels
Best Western Winchester Hotel, Hyatt Regency Lexington, The Manchester , GuestHouse Lexington, Quality Inn Lexington -Horse Park, La Quinta Inn & Suites by Wyndham Lexington South / Hamburg, Embassy Suites by Hilton Lexington/UK Coldstream, Hilton Lexington/Downtown, Tru by Hilton University Medical Center

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
Family vacations are where amazing memories are made, but traveling with children can be tricky. These kid-friendly Winchester hotels offer perks designed to keep travelers of all ages comfortable and happy: Your gang will enjoy staying at 2nd Story Historic Downtown 2BR with Modern Amenities. Pet-friendly facilities and free WiFi are among the things that help make this property an attractive option. Otherwise, spend your nights in Winchester at This house is a 3 bedroom(s), 2 bathrooms, located in Winchester, KY.. Take advantage of a king bed, pet-friendly facilities 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 CA $96 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 1,172 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 May, August and October. If you'd prefer the peace of off-season, book a stay during quieter months, such as December, January and February.
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

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Great place to stay!"
A verified traveller stayed at Everhome Suites Lexington - Horse Park
Everhome Suites Lexington - Horse Park

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Areas of Winchester