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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
$221 nightly
The price is $257 total per night from Sep 1 to Sep 2
$257 total
Sep 1 - Sep 2
Total includes 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 ...
"We loved the trendy vibe of the hotel — everything felt stylish but still cozy. We ended up eating most of our meals right at the hotel and honestly, the food didn’t disappoint. Service was consistently great, our bed was super comfortable, and the whole place was spotless. Would definitely recommend ..."

Reviewed on Jul 29, 2025

The Manchester
GLō Best Western Lexington

GLō Best Western Lexington

3 out of 5
1935 Stanton Way, Lexington, KY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Aug 11 to Aug 12
$109 total
Aug 11 - Aug 12
Total includes 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. ...
"As most of the reviews have mentioned, this hotels rooms are designed weird. With the blue cushion thing going across the wall. And the lights that dangle slightly above the nightstands. However, I wasn’t concerned about them. And found the lights to not be inconvenient at all. And I can look past ..."

Reviewed on Aug 4, 2025

GLō Best Western Lexington
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $78 total per night from Aug 24 to Aug 25
$78 total
Aug 24 - Aug 25
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 ...
"Overall this was a good place to stay. It was just about 20 minutes from anything in Lexington. Lots of dining and shopping options close by. My only real complaints are there were no drawers to put your clothes. And the mini fridge was about the size of a large cooler."

Reviewed on Aug 2, 2025

Spark by Hilton Lexington Hamburg
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
$121 nightly
The price is $140 total per night from Aug 17 to Aug 18
$140 total
Aug 17 - Aug 18
Total includes 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 ...
"It is a great place, we stay here a lot love everything about this hotel."

Reviewed on Jul 28, 2025

Marriott Lexington Griffin Gate Golf Resort & Spa
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

3 out of 5
2100 Hackney Pl, Lexington, KY
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $102 total per night from Aug 21 to Aug 22
$102 total
Aug 21 - Aug 22
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"Quiet, clean"

Reviewed on Jul 31, 2025

Fairfield Inn & Suites by Marriott Lexington North
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $73 total per night from Aug 19 to Aug 20
$73 total
Aug 19 - Aug 20
Total includes 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 ...
"Very clean and comfortable. Perfect for our stay en route to our vacation destination."

Reviewed on Aug 2, 2025

Quality Inn Lexington -Horse Park
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $82 total per night from Aug 11 to Aug 12
$82 total
Aug 11 - Aug 12
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business ...
"nice and clean. not fancy and over priced"

Reviewed on Aug 2, 2025

GuestHouse Lexington
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd, Winchester, KY
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $65 total per night from Aug 6 to Aug 7
$65 total
Aug 6 - Aug 7
Total includes 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.
"Nice clean place"

Reviewed on Jul 13, 2025

Value 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
$80 nightly
The price is $88 total per night from Aug 17 to Aug 18
$88 total
Aug 17 - Aug 18
Total includes 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 ...
"The staff was exceptionally friendly and the hotel, room and pool were very clean. But, the bed that we had was hard and pillows were lumpy and very uncomfortable."

Reviewed on Jul 28, 2025

Baymont 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 $65. 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 1,146 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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