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Find Family Hotels in Winchester, KY

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Check availability on Winchester Family Hotels

Our top choices for Winchester family-friendly hotels

Free daily full breakfast
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1001)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is ￥11,256
￥12,409 total
includes taxes & fees
Dec 21 - Dec 22
Best Western Winchester Hotel
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets
Value Stay

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (125)
"Awesome rooms and service"
United States
Brandon
The price is ￥10,386
￥11,449 total
includes taxes & fees
Dec 29 - Dec 30
Value Stay
Lobby
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (452)
"Would stay there again"
United States
Patricia
The price is ￥16,952
￥18,689 total
includes taxes & fees
Dec 28 - Dec 29
Hampton Inn Winchester
Indoor pool
Comfort Inn Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (352)
"The pool had no water. There was no pool available. There wasn't any hot water in our room. Unless you run it for 15/20 min"
United States
teresa
The price is ￥11,278
￥12,432 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Comfort Inn Winchester
Indoor pool
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (771)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is ￥12,434
￥13,707 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Baymont by Wyndham Winchester
Exterior
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (587)
"Great stay"
United States
Walter
The price is ￥9,658
￥10,647 total
includes taxes & fees
Dec 29 - Dec 30
Red Roof Inn Winchester - Lexington East
Interior
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Winchester
10.0 out of 10, Exceptional, (42)
"This home was beautiful and the hosts were overly generous with the amenities at the property. If we’re ever in the area again we will definitely be staying here! "
United States
Josiah C.
The price is ￥37,590
￥50,668 total
includes taxes & fees
Dec 29 - Dec 30
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Indoor pool, sun loungers
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

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, (1236)
"Friendly and Clean!"
United States
Roy
The price is ￥13,517
￥15,690 total
includes taxes & fees
Dec 18 - Dec 19
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Interior entrance
Quality Inn Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1005)
"The room was clean, staff so kind"
United States
Flor
The price is ￥13,796
￥15,208 total
includes taxes & fees
Dec 27 - Dec 28
Quality Inn Richmond
Property amenity
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park
2.5 star property
Lexington
9.2 out of 10, Wonderful, (414)
"Great place to stay!"
United States
Kristin
The price is ￥12,416
￥14,411 total
includes taxes & fees
Dec 29 - Dec 30
Everhome Suites Lexington - Horse Park
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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Top Winchester Hotel Reviews

Hilton Lexington/Downtown

Hilton Lexington/Downtown

10/10 Excellent
"Clean rooms and very freindly staff"
Matthew 1-night trip
Posted 1 day ago
Hilton Lexington/Downtown

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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.