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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
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 ...
"Very friendly staff, from check in to bar/restaurant to valets. That's not an accident. And the place is beautfiful, tidy and a little quirky. Would definitely stay again."

Reviewed on Jun 24, 2025

The Manchester
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive, Lexington, KY
Fully refundableReserve now, pay when you stay
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A lobby ...
Great Location
"The Ellwood is in a convenient location. Its very clean, secure, and service was excellent. Thought it odd that in a room with a king bed. There was only one chair. There is certainly room for another."

Reviewed on Jun 23, 2025

Elwood Hotel & Suites
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
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 ...
"Great people great location very clean"

Reviewed on Jun 23, 2025

Spark by Hilton Lexington Hamburg
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. Self parking, ...
"The outdoor pool was too close to the dumpster. The room is nice but the AC unit is way loud. Parking was plenty and easy. Most guests were supper friendly and courteous. Some guests on the same floor we stayed on Friday were inconsiderate and constantly entering and leaving and knocking and slamming ..."

Reviewed on Jun 24, 2025

DoubleTree Suites by Hilton Hotel Lexington
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
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 ...
"We had a nice quiet overnight stay to break up our long travel weekend. We booked a King suite for our family of 4. It was a great size! We were able to stretch out and not feel like we were in each other’s way. I usually hate hotels because of how noisy they can be, but I can say even with a convention ..."

Reviewed on Jun 23, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
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
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and ...
"Everything was great"

Reviewed on Jun 21, 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
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of ...
"Ice machine were all broken. Luggage carts were broken too. Room was clean & quiet."

Reviewed on Jun 24, 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
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 ...
"Clean, convenient. Quick breakfast, staff friendly and helpful"

Reviewed on Jun 23, 2025

GuestHouse Lexington
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
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 ...
"Very nice hotel. Staff was wonderful."

Reviewed on Jun 25, 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 . 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 1,139 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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