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Check availability on Winchester Family Hotels

Our top choices for Winchester family-friendly hotels

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, (128 reviews)
"Awesome rooms and service"
United States
Brandon
The price is ￥9,009
￥9,931 total
includes taxes & fees
Mar 20 - Mar 21
Value Stay
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 ￥16,245
￥17,908 total
includes taxes & fees
Feb 24 - Feb 25
Hampton Inn Winchester
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)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is ￥12,399
￥13,669 total
includes taxes & fees
Feb 22 - Feb 23
Best Western Winchester Hotel
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (778 reviews)
"Great place for a reasonable price! "
United States
Whitney
The price is ￥12,255
￥13,510 total
includes taxes & fees
Mar 15 - Mar 16
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 ￥10,515
￥11,592 total
includes taxes & fees
Mar 15 - Mar 16
Comfort Inn Winchester
Interior

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 reviews)
"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 ￥37,030
￥49,913 total
includes taxes & fees
Feb 18 - Feb 19
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
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 ￥9,513
￥10,487 total
includes taxes & fees
Mar 4 - Mar 5
Red Roof Inn Winchester - Lexington East
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, (1,187 reviews)
"Yes a very nice hotel "
United States
Dale
The price is ￥13,391
￥15,543 total
includes taxes & fees
Feb 18 - Feb 19
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
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, (2,217 reviews)
"Room was clean, staff was very helpful, easy parking, decent breakfast"
Canada
Christian
The price is ￥12,900
￥14,973 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express Lexington Horse Park Area by IHG
Daily cooked-to-order breakfast for a fee

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,004 reviews)
"Friendly staff at check in, comfortable bed"
Canada
Rochelle
The price is ￥14,743
￥17,112 total
includes taxes & fees
Feb 27 - Feb 28
Holiday Inn Lexington - Hamburg by IHG
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

Hilton Lexington/Downtown

Hilton Lexington/Downtown

10/10 Excellent
"Room was clean, staff was nice and all was good!"
Matthew 1-night trip
Posted 16 hours ago
Hilton Lexington/Downtown

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.