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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
$203 nightly
The price is $236 total per night from May 31 to Jun 1
$236 total
May 31 - Jun 1
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 ...
Amazing stay!

Reviewed on May 8, 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
$99 nightly
The price is $115 total per night from May 13 to May 14
$115 total
May 13 - May 14
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. ...
Since it’s changed ownership, I’m really disappointed that they do not offer coffee in the rooms anymore in the breakfast was just not as good as it had been last year under a different ownership, they said that the reason they weren’t offering coffee the rooms was because of the environment, however, ...

Reviewed on May 9, 2026

Opens in a new windowHoliday Inn Express Lexington Horse Park Area by IHG
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive Lexington KY
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $123 total per night from May 18 to May 19
$123 total
May 18 - May 19
Total with 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 ...
I just love staying at this hotel. It’s so unique in its style and overall atmosphere. I finally enjoyed the bar and restaurant this trip. The bartender was so nice and made a great cocktail! I tried the fried green tomato sliders… OMG! Outstanding. Also, it’s nice it’s so close to University of ...

Reviewed on May 8, 2026

Opens in a new windowElwood 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
$74 nightly
The price is $86 total per night from May 21 to May 22
$86 total
May 21 - May 22
Total with 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 ...
Was in town for a college visit and this was the perfect spot for an overnight stay. Clean property, friendly staff, and comfortable room. It was a quick trip for us but would definitely go back for a longer stay.

Reviewed on May 6, 2026

Opens in a new windowSpark by Hilton Lexington Hamburg
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
$126 nightly
The price is $139 total per night from May 11 to May 12
$139 total
May 11 - May 12
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 ...
While the lodge is rustic, it is clean and grounds are beautiful. The lodge is peaceful and quiet. The outdoor pool is amazing. The rooms are clean and the view of the woods and wildlife from your private balcony is beautiful. Breakfast buffet was fresh and hot and plenty of traditional and healthy ...

Reviewed on May 9, 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
$114 nightly
The price is $132 total per night from May 17 to May 18
$132 total
May 17 - May 18
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 ...
All excellent. Will be back.

Reviewed on May 9, 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
$157 nightly
The price is $183 total per night from May 17 to May 18
$183 total
May 17 - May 18
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 ...
Staff were great!

Reviewed on May 9, 2026

Opens in a new windowMarriott 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 $103 total per night from May 14 to May 15
$103 total
May 14 - May 15
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
Room was decently clean. Staff was distracted by what appeared to be an employee party being hosted there. The pool was ice cold and the advertised hot tub no longer exists. The main areas were all clean and the breakfast was good.

Reviewed on May 9, 2026

Opens in a new windowFairfield Inn & Suites by Marriott Lexington North
Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham

3 out of 5
5532 Athens Boonesboro Rd Lexington KY
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $98 total per night from May 12 to May 13
$98 total
May 12 - May 13
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, ...
Room was very clean. Had dinner in bar and staff was excellent and food was fresh and prepared as ordered. Free breakfast needs a little more variety.

Reviewed on May 9, 2026

Opens in a new windowHotel LEX, Trademark Collection by Wyndham
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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 $86. 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 1,200 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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