Hotels with a Pool in Winchester
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Tonight
Sep 6 - Sep 7Tomorrow
Sep 7 - Sep 8Next weekend
Sep 11 - Sep 13In two weeks
Sep 18 - Sep 20Hotels with a Pool in Winchester
Hampton Inn Winchester
Hampton Inn WinchesterWinchester
- Pool
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Connecting rooms available
$115
$127 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHGWinchester
- Indoor pool
$119
$131 total
includes taxes & fees
Sep 20 - Sep 21
Best Western Winchester Hotel
Best Western Winchester HotelWinchester
- Pool
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Connecting rooms available
$85
$94 total
includes taxes & fees
Sep 10 - Sep 11
$80
$88 total
includes taxes & fees
Sep 13 - Sep 14
Lexington Marriott City Center
Lexington Marriott City CenterDowntown Lexington
- Pool
- Parking available
- Free WiFi
- Restaurant
- Connecting rooms available
- Air conditioning
$201
$233 total
includes taxes & fees
Sep 13 - Sep 14
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
La Quinta Inn & Suites by Wyndham Lexington South / HamburgLexington
- Indoor pool
- Pool loungers
$90
$105 total
includes taxes & fees
Sep 13 - Sep 14
$71
$83 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Lexington - Horse Park Area by IHG
Holiday Inn Express Lexington - Horse Park Area by IHGLexington
- Indoor pool
- Pool loungers
$96
$111 total
includes taxes & fees
Sep 13 - Sep 14
$101
$117 total
includes taxes & fees
Sep 8 - Sep 9
$100
$110 total
includes taxes & fees
Sep 7 - Sep 8
Home2 Suites by Hilton Lexington Hamburg
Home2 Suites by Hilton Lexington HamburgLexington
- Indoor pool
$114
$132 total
includes taxes & fees
Sep 13 - Sep 14
$85
$99 total
includes taxes & fees
Sep 16 - Sep 17
Hilton Garden Inn Lexington Hamburg
Hilton Garden Inn Lexington HamburgLiberty Area
- Indoor pool
- Pool loungers
$88
$103 total
includes taxes & fees
Sep 20 - Sep 21
$104
$121 total
includes taxes & fees
Sep 7 - Sep 8
$72
$80 total
includes taxes & fees
Sep 27 - Sep 28
$69
$80 total
includes taxes & fees
Sep 13 - Sep 14
$84
$98 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Mt Sterling North by IHG
Holiday Inn Express & Suites Mt Sterling North by IHGMount Sterling
- Indoor pool
$127
$140 total
includes taxes & fees
Oct 4 - Oct 5
Hotel Lex and Conference Center, Trademark Collection
Hotel Lex and Conference Center, Trademark CollectionLexington
- Indoor pool
$81
$94 total
includes taxes & fees
Sep 14 - Sep 15
Fairfield Inn & Suites by Marriott Lexington North
Fairfield Inn & Suites by Marriott Lexington NorthLexington
- Indoor pool
$79
$92 total
includes taxes & fees
Sep 7 - Sep 8
Top landmarks in Winchester
Winchester Traveling Trail
If you like spending time outside, why not spend the afternoon at Winchester Traveling Trail, a park located 16.6 mi (26.8 km) from the center of Lexington. Want to stretch your legs some more? Head to Community Park and Wiseman Park, both nearby.
Bluegrass Heritage Museum
7.4/10 (13 reviews)
The center of Winchester is home to cultural attractions like Bluegrass Heritage Museum, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Community Park, Lykins Park, and Cassell Creek Golf Course.
Community Park
8.6/10 (66 reviews)
If you like spending time outside, why not spend the afternoon at Community Park, a park located 17.2 mi (27.7 km) from the center of Lexington. Want to stretch your legs some more? Head to Winchester Traveling Trail and Lykins Park, both nearby.
Cassell Creek Golf Course
7.6/10 (4 reviews)
You might want to practice your swing at Cassell Creek Golf Course, a golf course located 4.1 mi (6.6 km) from central Winchester. If Cassell Creek Golf Course doesn't quite scratch your golfing itch, Southwind Golf Course is also nearby.
Lykins Park
5.8/10 (6 reviews)
Lykins Park is 2 mi (3.3 km) from central Winchester, why not stop by during your stay. Want to stretch your legs some more? Head to Community Park and Winchester Traveling Trail, both nearby.
Southwind Golf Course
6.0/10 (2 reviews)
You might want to practice your swing at Southwind Golf Course, a golf course located 2.2 mi (3.5 km) from central Winchester. If Southwind Golf Course doesn't quite scratch your golfing itch, Cassell Creek Golf Course is also nearby.
Winchester Opera House
If you're planning a bit of sightseeing during your trip, head to Winchester Opera House— just one of the monuments in central Winchester.
Wiseman Park
If you like spending time outside, why not spend the afternoon at Wiseman Park, a park located 16.8 mi (27 km) from the center of Lexington. Want to stretch your legs some more? Head to Community Park and Lykins Park, both nearby.