Find Family Hotels in Winchester, KY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Family Hotels

Tonight
Jan 28 - Jan 29
Tomorrow
Jan 29 - Jan 30
This weekend
Jan 30 - Feb 1
Next weekend
Feb 6 - Feb 8

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, (1,000 reviews)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is NT$2,677
NT$2,951 total
includes taxes & fees
Jan 29 - Jan 30
Best Western Winchester Hotel
Lobby

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (456 reviews)
"Would stay there again"
United States
Patricia
The price is NT$3,328
NT$3,669 total
includes taxes & fees
Feb 15 - Feb 16
Hampton Inn Winchester
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (127 reviews)
"Awesome rooms and service"
United States
Brandon
The price is NT$2,108
NT$2,324 total
includes taxes & fees
Feb 2 - Feb 3
Value Stay
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (775 reviews)
"Great place for a reasonable price! "
United States
Whitney
The price is NT$2,381
NT$2,625 total
includes taxes & fees
Jan 29 - Jan 30
Baymont by Wyndham Winchester
Indoor pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (354 reviews)
"This was the second time we’ve stopped here this year. It’s the perfect halfway respite between our home town and our destination. Very clean and comfortable. We will tag this as a regular stop on other trips. "
United States
Noelle
The price is NT$2,273
NT$2,506 total
includes taxes & fees
Feb 28 - Mar 1
Comfort Inn Winchester
Exterior

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (589 reviews)
"Great stay"
United States
Walter
The price is NT$1,962
NT$2,163 total
includes taxes & fees
Feb 1 - Feb 2
Red Roof Inn Winchester - Lexington East
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, (2,226 reviews)
"Room was clean, staff was very helpful, easy parking, decent breakfast"
Canada
Christian
The price is NT$2,643
NT$3,068 total
includes taxes & fees
Feb 15 - Feb 16
Holiday Inn Express Lexington Horse Park Area by IHG
Interior entrance

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,018 reviews)
"The room was clean and the bed was super comfortable. "
United States
Elizabeth
The price is NT$2,800
NT$3,087 total
includes taxes & fees
Feb 7 - Feb 8
Quality Inn Richmond
Indoor pool, sun 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, (1,209 reviews)
"Yes a very nice hotel "
United States
Dale
The price is NT$2,744
NT$3,185 total
includes taxes & fees
Feb 11 - Feb 12
La Quinta Inn & Suites by Wyndham Lexington South / 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.
View all properties

Top Winchester Hotel Reviews

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

10/10 Excellent
"Everything was great. Thank you."
Emily 5-night trip
Posted 16 hours ago
Spark by Hilton Lexington Hamburg

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.

Explore a world of travel with Expedia