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
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for Winchester family-friendly hotels

A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

1. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (487 reviews)
"Close to Red River Gorge hiking."
United States
kelly
The price is NT$3,297
NT$3,635 total
includes taxes & fees
Nov 24 - Nov 25
Hampton Inn Winchester
A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

2. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,005 reviews)
"They have a really good Breakfast..."
United States
David
The price is NT$2,787
NT$3,072 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.

3. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (865 reviews)
"Room was clean beds were comfortable"
United States
Ronald
The price is NT$2,601
NT$2,868 total
includes taxes & fees
Nov 9 - Nov 10
Baymont by Wyndham Winchester
A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.

4. 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, (614 reviews)
"This is one of the nicest and cleanest Holiday Inns I’ve ever been to. Very friendly staff too."
United States
Stephen
The price is NT$3,814
NT$4,205 total
includes taxes & fees
Dec 3 - Dec 4
Holiday Inn Express Lexington East - Winchester by IHG
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, (194 reviews)
"Well worth the money"
United States
Ronald
The price is NT$1,923
NT$2,120 total
includes taxes & fees
Nov 11 - Nov 12
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)
"Pool was closed other than that overall good hotel"
United States
james
The price is NT$2,490
NT$2,744 total
includes taxes & fees
Nov 28 - Nov 29
Comfort Inn Winchester
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

Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

10/10 Excellent
"Clean room, very comfortable bed"
Melitza 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Lexington - Hamburg I-75

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.

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