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Top Winchester hotels

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $225 total per night from Jul 5 to Jul 6
$225 total
Jul 5 - Jul 6
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, express ...
"Front desk & valet service (Omar) were very friendly, great location, we loved riding the complimentary bikes!"

Reviewed on Jun 22, 2026

Opens in a new windowThe Manchester
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
$94 nightly
The price is $109 total per night from Jul 19 to Jul 20
$109 total
Jul 19 - Jul 20
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. ...
"The pool was nice, the staff was friendly, the breakfast was great"

Reviewed on Jun 23, 2026

Opens in a new windowHoliday Inn Express Lexington Horse Park Area by IHG
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
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $105 total per night from Jun 28 to Jun 29
$105 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"I love staying at this hotel every time we go up to Ohio. We always stay here on the way up and then on the way back from our vacation. Rates are always great. I love that You can have two dogs and Pets stay free. That is a big, huge, huge bonus. The beds are amazing friendly staff good breakfast ..."

Reviewed on Jun 24, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $150 total per night from Jul 19 to Jul 20
$150 total
Jul 19 - Jul 20
Total with taxes and fees
This cabin features a restaurant, a seasonal outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free ...
"We booked a cottage last minute for an overnight stay at the park and it's definitely worth a longer stay."

Reviewed on Jun 23, 2026

Opens in a new windowNatural Bridge State Resort Park
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 out of 5
1801 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $104 total per night from Jun 28 to Jun 29
$104 total
Jun 28 - Jun 29
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 WiFi in public areas. Relax ...
"The hotel and staff were great. The breakfast and happy hour were really good as well. Only one elevator was working so it took a long time to get up and down from our room. The housekeeping was sporadic in the sense that they were very busy and a couple of days did not get to our room until much ..."

Reviewed on Jun 23, 2026

Opens in a new windowEmbassy Suites by Hilton Lexington/UK Coldstream
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $140 total per night from Jun 28 to Jun 29
$140 total
Jun 28 - Jun 29
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, express ...
"AC wouldn’t keep room cool. Front desk staff wasn’t always available or terribly helpful. Room fridge didn’t keep things cool & no microwave in room. Bathroom fixtures were in moderately poor repair. Great location & the room service food available was outstanding, however."

Reviewed on Jun 22, 2026

Opens in a new windowMarriott Lexington Griffin Gate Golf Resort & Spa
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way Lexington KY
Fully refundable
$66 nightly
The price is $77 total per night from Jul 20 to Jul 21
$77 total
Jul 20 - Jul 21
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of ...
"I enjoyed my stay and would have stayed Monday and Tuesday if the rates hadn’t gone up"

Reviewed on Jun 23, 2026

Opens in a new windowQuality Inn Lexington -Horse Park
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd Winchester KY
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $72 total per night from Jun 25 to Jun 26
$72 total
Jun 25 - Jun 26
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.
"While the room was clean and maintained, the only grip I had was its location and the road you had to travel to reach the hotels. A sign would have been nice so drivers won't get lost on their first time getting to the hotel."

Reviewed on Jun 14, 2026

Opens in a new windowValue Stay
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $87 total per night from Jul 1 to Jul 2
$87 total
Jul 1 - Jul 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will ...
"Great people clean rooms and the pool works"

Reviewed on Jun 8, 2026

Opens in a new windowBaymont by Wyndham Winchester
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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.

Cheap Winchester hotels

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.

Winchester Hotel & Travel Guide\n

Since the days when it was a small town on the Western frontier, the power of the human character has driven Winchester, Kentucky to ever-greater achievements. Nestled amongst the rolling hills of the famed Bluegrass Region, the gorgeous scenery and down-to-earth locals will make you want to stay forever, while the inimitable pioneer spirit will also inspire you to see out great adventures from hotels in Winchester, KY.

Visiting Winchester

Are the scents of the day’s delicious meals already wafting through your curtains when you wake at Winchester hotels? It won’t be long until you indulge, but for now, follow the sounds of babbling brooks and gentle songbirds to Lower Howard’s Creek Nature and Heritage Preserve. In the spring, a sea of indigo overtakes the preserve as bluebells, Jacob’s ladder, and larkspur burst into color and friendly river otters wave hello from the riverbanks.

It will soon be time for sustenance, and Travelocity’s Winchester rental cars can take you on culinary pursuits to satisfy any palate. On the Beer Cheese Trail, let the delectable flavors of cheddar, beer and spices melt in your mouth—there is nothing on earth quite like Kentucky beer cheese, and you are lucky enough to be in its birthplace. Yearning for more? Whether you crave a classic, juicy American hot dog with all the accoutrements or fresh, country-style fish with more hush puppies than you can eat, Winchester’s Bypass Road is sure to satisfy.

Seventy-five miles west, Louisville also offers plenty of opportunity for edible adventures. While the flavors of smoky pulled pork linger in your mind, you sip a first-rate bourbon and let the toasted oak and caramel dance along your taste buds and warm your soul. After such exploits, you’ll be more than happy to slip under the covers at any of our superb Louisville hotels.

Thanks to the incredible souls who came before you and built their version of the American dream, no wish must remain unexplored in this Southern paradise. Book hotels near Winchester with Travelocity today, and your vacation fantasies can start coming true tomorrow.

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 $72. 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 1,201 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.

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