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.

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Check availability on Winchester Family Hotels

This weekend
26 Jun - 28 Jun
Next weekend
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, (1,003 reviews)
The price is AED 331
AED 365 total
includes taxes & fees
29 Jun - 30 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 AED 278
AED 306 total
includes taxes & fees
23 Jun - 24 Jun
Baymont by Wyndham Winchester
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (158 reviews)
The price is AED 239
AED 263 total
includes taxes & fees
23 Jun - 24 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 vacation magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
The price is AED 514
AED 567 total
includes taxes & fees
24 Jun - 25 Jun
Hampton Inn Winchester
Pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (368 reviews)
The price is AED 275
AED 303 total
includes taxes & fees
20 Jul - 21 Jul
Comfort Inn Winchester
Combined shower/tub, 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 AED 149
AED 173 total
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, (1,001 reviews)
The price is AED 364
AED 401 total
includes taxes & fees
5 Jul - 6 Jul
Quality Inn Richmond
Suite, 1 King Bed with Sofa bed, Non Smoking, Hot Tub | Desk, laptop workspace, iron/ironing board, free cribs/infant beds

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 vacation memories together.
The price is AED 192
AED 212 total
includes taxes & fees
20 Jul - 21 Jul
Comfort Suites 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, (1,168 reviews)
  • cleanliness
    Create unforgettable family memories at a hotel with an indoor pool, premium entertainment, and complimentary breakfast included.
The price is AED 332
AED 386 total
includes taxes & fees
5 Jul - 6 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 AED 349
AED 661 total
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

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

10/10 Excellent
"Property was very nice and clean. The room was spacious and was a short drive to multiple activities."
Kenneth 2-night trip
Posted 7 hours ago
DoubleTree Suites by Hilton Hotel Lexington

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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.