An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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Check availability on Winchester Family friendly Hotels

Our top choices for Winchester family-friendly hotels

Indoor pool, open 5:00 AM to 10:00 PM, pool loungers

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,207 reviews)
The price is S$138
includes taxes & fees
22 Jul - 23 Jul
Holiday Inn Express Lexington - Horse Park Area by IHG
Indoor pool, pool loungers

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,184 reviews)
  • cleanliness
    Create unforgettable family memories at a hotel with an indoor pool, premium entertainment, and complimentary breakfast included.
The price is S$136
includes taxes & fees
16 Jul - 17 Jul
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Interior entrance

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,005 reviews)
The price is S$154
includes taxes & fees
9 Aug - 10 Aug
Quality Inn Richmond
Lobby

Best Western Plus Georgetown Corporate Center Hotel

Best Western Plus Georgetown Corporate Center Hotel
2.5 star property
Georgetown
8.6 out of 10, Excellent, (1,008 reviews)
  • cleanliness
    Discover a family paradise with pool, hot tub, and cots just minutes from Kentucky Horse Park for memorable stays.
The price is S$120
includes taxes & fees
12 Jul - 13 Jul
Best Western Plus Georgetown Corporate Center Hotel
Lobby

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream
3.5 star property
Lexington
8.6 out of 10, Excellent, (1,139 reviews)
  • cleanliness
    Splash into family fun at this Lexington hotel with an indoor pool, spacious suites, and free breakfast made to order.
The price is S$171
includes taxes & fees
2 Aug - 3 Aug
Embassy Suites by Hilton Lexington/UK Coldstream
Free daily buffet breakfast

Home2 Suites Lexington Keeneland Airport, KY

Home2 Suites Lexington Keeneland Airport, KY
3.0 star property
Beaumont Residential
9.8 out of 10, Exceptional, (377 reviews)
The price is S$133
includes taxes & fees
19 Jul - 20 Jul
Home2 Suites Lexington Keeneland Airport, KY
Lobby

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (473 reviews)
  • cleanliness
    Family holiday magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
The price is S$174
includes taxes & fees
19 Jul - 20 Jul
Hampton Inn Winchester
Combined shower/bathtub, free toiletries, towels

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,005 reviews)
  • cleanliness
    Family-friendly escape in Lexington offers comfortable rooms, convenient breakfast options, and easy access to local attractions.
The price is S$93
includes taxes & fees
13 Jul - 14 Jul
Days Inn Lexington SE/Hamburg
Indoor pool

Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
2.5 star property
Lexington
8.6 out of 10, Excellent, (1,006 reviews)
The price is S$137
includes taxes & fees
22 Jul - 23 Jul
Hampton Inn I-75 Lexington/Hamburg Area
Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,007 reviews)
The price is S$122
includes taxes & fees
26 Jul - 27 Jul
Best Western Winchester Hotel
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.
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Choose what matters most at family-friendly hotels in Winchester

Pool
Breakfast included

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Great stay. Rooms clean and spacious. Beautiful lobby and very good breakfast. Highly recommend"
norman 1-night trip
Posted 3 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream

Frequently asked questions

What's Winchester like for family-friendly holidays?
The welcoming destination of Winchester is a great choice if you've been thinking about a holiday with the children. The excursions, American football matches and cafes are just some of the things that make this an attractive spot for a family holiday. Arrange a flight into Lexington, KY (LEX-Blue Grass), which is located 23 mi (37.1 km) from the city centre.
What's the best family accommodation in Winchester?
Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly holiday in Winchester?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you may want to round up the youngsters and make time to see interesting attractions such as Clark County Public Library and Lexington Sporting Club Youth Complex. Make sure that you have lots of time for activities such as Hamburg Pavilon and Hamburg Place.

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