Winchester Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Winchester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
GuestHouse Lexington
$649
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rupp Arena and Kroger Field are located nearby.
I was only there one night but it was very nice. I was not able to use anything because on no time.
Reviewed on Aug 25, 2026
Candlewood Suites Lexington Medical District by IHG
South Broadway Park
$779
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kroger Field and Rupp Arena are located nearby.
The beds and pillows should be against the law they were so comfortable!!! Very nice place will stay again! 10/10 will recommend!!!
Reviewed on Aug 25, 2026
Holiday Inn Express Lexington - Horse Park Area by IHG
$827
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
Stay at this hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Kentucky Horse Park and Rupp Arena are located nearby.
Well priced, clean, and comfortable
Reviewed on Aug 25, 2026
Marriott Lexington Griffin Gate Golf Resort & Spa
$711
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
Book a stay at this luxury resort in Lexington. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Rupp Arena and Kentucky Horse Park are located nearby.
Everything was great
Reviewed on Aug 25, 2026
Elwood Hotel & Suites
$1,186
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
Stay at this hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Kroger Field and Rupp Arena are located nearby.
Everhome Suites Lexington - Horse Park
$737
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Rupp Arena and Kroger Field are located nearby.
Needed. more towels I had to bring used one Dow n…. Not
Reviewed on Aug 20, 2026
Top Hotel Deals
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Stay at this hotel in Lexington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
The Manchester
941 Manchester St Lexington KY
Stay at this hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular ...
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Book a stay at this luxury resort in Lexington. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff ...
Holiday Inn Express Lexington - Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Stay at this hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Embassy Suites by Hilton Lexington/UK Coldstream
1801 Newtown Pike Lexington KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
Origin Lexington a Wyndham Hotel
4174 Rowan Lexington KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
Natural Bridge State Resort Park
2135 Natural Bridge Road Slade KY
Stay at this cabin in Slade. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Fairfield Inn & Suites by Marriott Lexington North
2100 Hackney Pl Lexington KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
GuestHouse Lexington
2261 Elkhorn Road Lexington KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
21c Museum Hotel Lexington
167 West Main Street Lexington KY
Stay at this hotel in Lexington. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. ...
Elwood Hotel & Suites
444 Parkway Drive Lexington KY
Stay at this hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. ...
The Campbell House Lexington, Curio Collection by Hilton
1375 South Broadway Lexington KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our ...
Staybridge Suites Lexington S Medical Ctr Area by IHG
209 RUCCIO WAY Lexington KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Lexington - Hamburg by IHG
1976 Justice Dr Lexington KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 21 - Tue, Oct 27
JFK
John F. Kennedy Intl.
LEX
Blue Grass
$291
Roundtrip
found 12 hours ago
Wed, Oct 21 - Tue, Oct 27
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$291
Roundtrip
found 12 hours ago
Wed, Oct 21 - Tue, Oct 27
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$291
Roundtrip
found 12 hours ago
Mon, Sep 28 - Fri, Oct 16
IAH
George Bush Intercontinental
LEX
Blue Grass
$345
Roundtrip
found 17 hours ago
Best points of interest in Lexington
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All accommodation types in Winchester
More Types of Hotels
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