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.

Family friendly Hotels in Winchester, Lexington

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Check availability on Winchester Family friendly Hotels

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

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 P5,824
P6,420 total
includes taxes & fees
Jun 29 - Jun 30
Best Western Winchester Hotel
Free WiFi, bed sheets

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (158 reviews)
The price is P3,985
P4,393 total
includes taxes & fees
Jun 29 - Jun 30
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 P4,690
P5,171 total
includes taxes & fees
Jul 26 - Jul 27
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 P4,560
P5,027 total
includes taxes & fees
Jul 27 - Jul 28
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 vacation magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
The price is P8,195
P9,034 total
includes taxes & fees
Jul 29 - Jul 30
Hampton Inn Winchester
Indoor pool, open 5:00 AM to 10:00 PM, sun 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 P6,315
P7,330 total
includes taxes & fees
Jul 21 - Jul 22
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 center, and complimentary breakfast buffet.
The price is P4,221
P4,653 total
includes taxes & fees
Jul 5 - Jul 6
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 P5,457
P6,333 total
includes taxes & fees
Jul 5 - Jul 6
Home2 Suites Lexington Keeneland Airport, KY
Combined shower/tub, 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 P2,789
P3,237 total
includes taxes & fees
Jun 30 - Jul 1
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

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

8/10 Good
"Beautiful property and very clean, just needs a few maintenance updates, but the property is very old and historic."
Kaela 2-night trip
Posted 1 hour ago
The Campbell House Lexington, Curio Collection by Hilton

Frequently asked questions

What's Winchester like for family-friendly vacations?
The welcoming destination of Winchester is a great choice if you've been thinking about a vacation with the kids. The excursions, football games, and cafes are just some of the things that make this an attractive family vacation spot. Arrange a flight into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) from the city center.
What's the best place to stay for families 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 vacation in Winchester?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you might want to round up the kiddos and make time to see interesting attractions such as Clark County Public Library and Lexington Sporting Club Youth Complex. Make sure you have lots of time for activities like Hamburg Pavilon and Hamburg Place.

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