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.

Winchester Hotel Guide - Family Friendly Hotels in Winchester, Lexington

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Check availability on Winchester Family Friendly Hotels

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul

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, (1,002 reviews)
The price is €87
includes taxes & fees
25 Jun - 26 Jun
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, (812 reviews)
  • cleanliness
    Family-friendly hotel offers indoor swimming, free breakfast, and nearby park for all-ages adventure.
The price is €73
includes taxes & fees
22 Jun - 23 Jun
Baymont by Wyndham Winchester
Suite, 1 King Bed, Hot Tub

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (158 reviews)
The price is €62
includes taxes & fees
22 Jun - 23 Jun
Value Stay
Lobby

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (471 reviews)
  • cleanliness
    Family holiday magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
The price is €135
includes taxes & fees
23 Jun - 24 Jun
Hampton Inn Winchester
Pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (367 reviews)
The price is €72
includes taxes & fees
19 Jul - 20 Jul
Comfort Inn Winchester
Combined shower/bathtub, free toiletries, towels

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,002 reviews)
  • cleanliness
    Family-friendly escape in Lexington offers comfortable rooms, convenient breakfast options, and easy access to local attractions.
The price is €40
includes taxes & fees
30 Jun - 1 Jul
Days Inn Lexington SE/Hamburg
Interior entrance

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,000 reviews)
The price is €99
includes taxes & fees
12 Jul - 13 Jul
Quality Inn Richmond
Suite, 1 King Bed with Sofa bed, Non Smoking, Hot Tub

Comfort Suites Richmond

Comfort Suites Richmond
2.5 star property
Richmond
7.4 out of 10, Good, (760 reviews)
  • cleanliness
    Comfort Suites Richmond offers an indoor pool paradise where families can swim, play, and make lasting holiday memories together.
The price is €48
includes taxes & fees
20 Jul - 21 Jul
Comfort Suites Richmond
Indoor pool, pool 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, (1,167 reviews)
  • cleanliness
    Create unforgettable family memories at a hotel with an indoor pool, premium entertainment, and complimentary breakfast included.
The price is €92
includes taxes & fees
2 Jul - 3 Jul
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Smart TV, fireplace, books

Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (112 reviews)
The price is €161
includes taxes & fees
16 Jul - 17 Jul
Unique Stay in a 1907 Log Cabin on The Kentucky River
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Check-In was very good and helpful👍. Room was large and clean. Overall a very positive experience."
Matthew 2-night trip
Posted 3 hours ago
Elwood Hotel & Suites

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.