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

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Winchester family-friendly hotels

Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,001 reviews)
The price is Rp1.617.281
Rp1.782.891 total
includes taxes & fees
12 Jul - 13 Jul
Best Western Winchester Hotel
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (158 reviews)
The price is Rp1.164.930
Rp1.284.291 total
includes taxes & fees
29 Jun - 30 Jun
Value Stay
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (816 reviews)
  • cleanliness
    Family-friendly hotel offers indoor swimming, free breakfast, and nearby park for all-ages adventure.
The price is Rp1.371.033
Rp1.511.541 total
includes taxes & fees
26 Jul - 27 Jul
Baymont by Wyndham Winchester
Pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (369 reviews)
The price is Rp1.333.038
Rp1.469.540 total
includes taxes & fees
27 Jul - 28 Jul
Comfort Inn Winchester
Lobby

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (471 reviews)
  • cleanliness
    Family holiday magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
The price is Rp2.380.758
Rp2.624.547 total
includes taxes & fees
26 Jul - 27 Jul
Hampton Inn Winchester
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, (2,198 reviews)
The price is Rp1.845.966
Rp2.142.613 total
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Express Lexington Horse Park Area by IHG
Lobby

Baymont by Wyndham Georgetown/Lexington North

Baymont by Wyndham Georgetown/Lexington North
2.5 star property
Georgetown
8.0 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Family fun at this Georgetown hotel with an indoor pool, fitness centre, and complimentary breakfast buffet.
The price is Rp1.233.930
Rp1.360.285 total
includes taxes & fees
5 Jul - 6 Jul
Baymont by Wyndham Georgetown/Lexington North
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, (368 reviews)
The price is Rp1.523.370
Rp1.768.176 total
includes taxes & fees
4 Jul - 5 Jul
Home2 Suites Lexington Keeneland Airport, KY
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, (1,003 reviews)
  • cleanliness
    Family-friendly escape in Lexington offers comfortable rooms, convenient breakfast options, and easy access to local attractions.
The price is Rp815.272
Rp946.282 total
includes taxes & fees
30 Jun - 1 Jul
Days Inn Lexington SE/Hamburg
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"The room was spacious and clean, check in was easy, and I loved the walk in accessibility!"
Rebecca 1-night trip
Posted 3 hours ago
Elwood Hotel & Suites

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.