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Check availability on Winchester Family-Friendly Hotels

Our top choices for Winchester family-friendly hotels

Seasonal outdoor pool

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 Rp1.283.961
Rp1.415.438 total
includes taxes & fees
21 Feb - 22 Feb
Best Western Winchester Hotel
Seasonal outdoor pool

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 Rp1.997.147
Rp2.201.655 total
includes taxes & fees
15 Feb - 16 Feb
Hampton Inn Winchester
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 Rp1.269.022
Rp1.399.113 total
includes taxes & fees
15 Feb - 16 Feb
Baymont by Wyndham 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 Rp990.374
Rp1.091.761 total
includes taxes & fees
1 Mar - 2 Mar
Value Stay
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 Rp1.152.213
Rp1.270.199 total
includes taxes & fees
15 Mar - 16 Mar
Comfort Inn Winchester
Deluxe Room, 1 King Bed, Non Smoking | Desk, blackout curtains, free WiFi, bed sheets

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 Rp1.045.785
Rp1.152.872 total
includes taxes & fees
24 Feb - 25 Feb
Red Roof Inn Winchester - Lexington East
Seasonal outdoor pool, open 9 AM to 10 PM, pool loungers

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean room, friendly staff, quiet"
United States
Marjorie
The price is Rp1.493.954
Rp1.646.874 total
includes taxes & fees
16 Feb - 17 Feb
Quality Inn Richmond
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, (2,216 reviews)
"Room was clean, staff was very helpful, easy parking, decent breakfast"
Canada
Christian
The price is Rp1.410.024
Rp1.636.614 total
includes taxes & fees
15 Feb - 16 Feb
Holiday Inn Express Lexington Horse Park Area by IHG
Standard Room, 1 King Bed with Sofa bed | Premium bedding, down duvets, pillow-top beds, desk

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,001 reviews)
"Friendly staff at check in, comfortable bed"
Canada
Rochelle
The price is Rp1.611.456
Rp1.870.416 total
includes taxes & fees
28 Feb - 1 Mar
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

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

10/10 Excellent
"Good value "
Geraldine 1-night trip
Posted 1 day ago
Spark by Hilton Lexington Hamburg
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"Clean room, comfortable bed, and friendly staff. Plenty of space to enjoy time with friends. Love the large food and drink selection as well. "
Alan 2-night trip
Posted 5 days ago
Embassy Suites by Hilton Lexington Green

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.