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Family friendly Hotels in Winchester, Kentucky

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Check prices for these dates

Tonight
Nov 11 - Nov 12
Tomorrow
Nov 12 - Nov 13
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Winchester family-friendly hotels

A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.

1. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (616 reviews)
The price is P6,902
P7,609 total
includes taxes & fees
Nov 14 - Nov 15
Holiday Inn Express Lexington East - Winchester by IHG
A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

2. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (487 reviews)
  • cleanliness
    Family vacation magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
The price is P6,956
P7,668 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Winchester
A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,001 reviews)
The price is P5,381
P5,932 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Winchester Hotel
A swimming pool with wooden walls and large windows offering views of greenery.

4. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (867 reviews)
  • cleanliness
    Family-friendly hotel offers indoor swimming, free breakfast, and nearby park for all-ages adventure.
The price is P5,023
P5,538 total
includes taxes & fees
Nov 19 - Nov 20
Baymont by Wyndham Winchester
A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

5. Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (201 reviews)
The price is P3,714
P4,094 total
includes taxes & fees
Nov 20 - Nov 21
Value Stay
An indoor swimming pool with tiled flooring, orange walls, and potted plants.

6. Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (397 reviews)
The price is P4,922
P5,427 total
includes taxes & fees
Dec 2 - Dec 3
Comfort Inn Winchester
An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.

7. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,175 reviews)
  • cleanliness
    Create unforgettable family memories at a hotel with an indoor pool, premium entertainment, and complimentary breakfast included.
The price is P5,489
P6,371 total
includes taxes & fees
Nov 15 - Nov 16
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A large indoor swimming pool with a tiled floor, surrounded by large windows and a seating area with tables and chairs.

8. 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, (2,242 reviews)
The price is P5,351
P6,210 total
includes taxes & fees
Dec 10 - Dec 11
Holiday Inn Express Lexington - Horse Park Area by IHG
A pool table in a modern lounge area with a bar and seating.

9. Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (308 reviews)
The price is P5,110
P5,931 total
includes taxes & fees
Nov 29 - Nov 30
Tru By Hilton Lexington Hamburg
A modern kitchen with grey cabinets, a wooden dining table, and overhead lighting.

10. Homewood Suites Lexington-Hamburg

Homewood Suites Lexington-Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (731 reviews)
  • cleanliness
    Family vacation fun awaits with outdoor pools, firepits, and 24-hour fitness centers just minutes from Lexington's top attractions.
The price is P6,902
P8,011 total
includes taxes & fees
Nov 22 - Nov 23
Homewood Suites Lexington-Hamburg
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

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 Hamburg Pavilion. Make sure you have lots of time for activities like Hamburg Place and Claiborne Farm.