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Top Winchester hotels

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive, Lexington, KY
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $127 total per night from Jul 27 to Jul 28
$127 total
Jul 27 - Jul 28
Total includes taxes and fees
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 ...
Exceptional
"Great stay and we will stay again"

Reviewed on Jul 21, 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
$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 ...
"Hotel was clean and pretty. Hotel staff were awesome and friendly!"

Reviewed on Jul 21, 2025

Spark by Hilton Lexington Hamburg
Hyatt Place Lexington

Hyatt Place Lexington

3 out of 5
2001 Bryant Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $111 total per night from Aug 8 to Aug 9
$111 total
Aug 8 - Aug 9
Total includes taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
"Hotel and Staff are supurb, all round very nice and worth staying at."

Reviewed on Jul 21, 2025

Hyatt Place Lexington
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
$136 nightly
The price is $158 total per night from Aug 24 to Aug 25
$158 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the express check-out, laundry service, and free airport ...
"Overall, it was a good stay. Thr beds were uncomfortable and sunk in the middle"

Reviewed on Jul 20, 2025

Hilton Lexington/Downtown
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
$71 nightly
The price is $82 total per night from Jul 30 to Jul 31
$82 total
Jul 30 - Jul 31
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. Enjoy the hot tub and ...
"Easy access"

Reviewed on Jul 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
$67 nightly
The price is $77 total per night from Jul 27 to Jul 28
$77 total
Jul 27 - Jul 28
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 ...
"This was one of my better choice"

Reviewed on Jul 22, 2025

Quality Inn Lexington -Horse Park
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd, Winchester, KY
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $63 total per night from Jul 30 to Jul 31
$63 total
Jul 30 - Jul 31
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
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $77 total per night from Aug 3 to Aug 4
$77 total
Aug 3 - Aug 4
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 ...
"I like that it wasnt so overcrowded and was perfect for our overnight stay. And the pricing was awesome as well."

Reviewed on Jul 22, 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
$80 nightly
The price is $88 total per night from Jul 30 to Jul 31
$88 total
Jul 30 - Jul 31
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 ...
"My 5 star review is in part due to the staff. They were so kind, helpful, and went out of their way, on several occasions, to make our stay better. The rooms have laminate floors. I love this because their is no smell from old carpet. The room and bathroom were clean, the beds were clean and acceptable. ..."

Reviewed on Jul 17, 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 $63. 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 1,149 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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