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-Friendly Hotels

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov

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 ₹9,605
₹10,588 total
includes taxes & fees
26 Nov - 27 Nov
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, (1,002 reviews)
"They have a really good Breakfast..."
United States
David
The price is ₹8,118
₹8,949 total
includes taxes & fees
1 Dec - 2 Dec
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, (864 reviews)
"Room was clean beds were comfortable"
United States
Ronald
The price is ₹7,577
₹8,353 total
includes taxes & fees
8 Nov - 9 Nov
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 ₹11,300
₹12,457 total
includes taxes & fees
19 Nov - 20 Nov
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, (193 reviews)
"Well worth the money"
United States
Ronald
The price is ₹5,322
₹5,867 total
includes taxes & fees
13 Nov - 14 Nov
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 ₹7,252
₹7,994 total
includes taxes & fees
28 Nov - 29 Nov
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

GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"We were so pleased with the quality of Guest House Lexington. The room was so clean, beds were comfy and the staff was friendly. We would definitely stay there again! Great location"
Jo 3-night trip
Posted less than an hour ago
GuestHouse Lexington

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