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

Tonight
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Winchester family-friendly hotels

A Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.
A modern bathroom with a large mirror, a sink, and a toilet.
A modern office space with two desks, chairs, and computers.
A hotel room with two beds, a nightstand, a lamp, and a chair.

1. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester
€96
includes taxes & fees
16 Nov - 17 Nov
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.
A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.
A reception desk with a 'Manager On Duty' sign, framed pictures on the wall, and a 'Welcome to Winchester' sign.
A bathroom with a sink, mirror, shower, and towel rack.

2. Hampton Inn Winchester

Hampton Inn Winchester
Winchester
  • Family holiday magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
€108
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn Winchester
A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.
A lobby with two armchairs, a reception desk, and a chandelier.
A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.
A modern bathroom with a granite countertop sink, a white toilet, a bathtub, and a large mirror.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
€98
includes taxes & fees
25 Oct - 26 Oct
Best Western Winchester Hotel
A swimming pool with wooden walls and large windows offering views of greenery.
A hotel room with two beds, a sofa, a desk, and a window with blinds.
A modern lobby with a sofa, armchair, and a coffee table. A flat-screen TV is mounted on the wall, and there is a window with a view of a tree and building.
A hotel dining area with a coffee station, a clock, and large windows offering a view of the outside.

4. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
Winchester
  • Family-friendly hotel offers indoor swimming, free breakfast, and nearby park for all-ages adventure.
€74
includes taxes & fees
16 Nov - 17 Nov
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.
Bathroom
Reception
A lobby with a patterned carpet, seating area with chairs and a sofa, a small table, and a reception desk.

5. Value Stay

Value Stay
Winchester
€58
includes taxes & fees
11 Nov - 12 Nov
Value Stay
An indoor swimming pool with tiled flooring, orange walls, and potted plants.
A waiting area with blue sofas and a brown ottoman, a reception desk, and a door leading to a hallway.
A bathroom with a bathtub, a chair, and a small ottoman.
A hotel room with a large bed, a bedside table with a lamp, and a telephone.

6. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
€68
includes taxes & fees
16 Nov - 17 Nov
Comfort Inn Winchester
A bedroom with a bed, a chair, a wooden cabinet, and a door leading to another room.
A street with buildings on both sides, including a white building with columns on the left and a row of shops on the right.
A historic building with a clock tower, large windows, and a street view with parked cars.
A building with a storefront labeled "Cupcake Apothecary."

7. 2nd Story Historic Downtown 2BR with Modern Amenities

2nd Story Historic Downtown 2BR with Modern Amenities
Winchester
€156
includes taxes & fees
20 Oct - 21 Oct
2nd Story Historic Downtown 2BR with Modern Amenities
A playground with swings and a fenced play area.
A two-story house with a covered porch, a brick exterior, and a small garden area with shrubs.
A bedroom with a bed, a dresser, a nightstand, a ceiling fan, and a TV mounted on the wall.
A kitchen with wooden cabinets, a stainless steel refrigerator, a dishwasher, and a window above the sink.

8. The Winchester

The Winchester
Winchester
€255
includes taxes & fees
20 Oct - 21 Oct
The Winchester
A kitchen with white cabinets, a stainless steel oven, and a dishwasher.
A living room with a beige sofa set, a wooden coffee table, and a recliner.
A corner bathroom with a shower, toilet, and sink.
A living room with a sofa, armchair, and coffee table. There is a ceiling fan and a TV mounted on the wall.

9. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
€255
includes taxes & fees
25 Oct - 26 Oct
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A modern bathroom with a shower, toilet, vanity, and a large mirror with lights.
A dining room with a wooden table, chairs, a chandelier, and a cabinet with glass doors.
A two-story house with a front porch, surrounded by a well-maintained lawn and large trees.
A living room with a piano, a sofa, a table, and a chair.

10. Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Winchester
€286
includes taxes & fees
20 Oct - 21 Oct
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
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Choose what matters most at family-friendly hotels in Winchester

Pool
Breakfast included
All-inclusive
4 stars
5 stars

Top Winchester Hotel Reviews

Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"Enjoyed on site bar and outdoor areas"
Suzanne 3-night trip
Posted 10 hours ago
Marriott Lexington Griffin Gate Golf Resort & Spa
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"We had a great stay! Everything was very clean. The breakfast was amazing with made to order omelettes & waffles & very spacious dining room. It would have been nice to have queens beds instead of double size, but for one night, it was fine. Overall a positive experience!"
Kimberly 1-night trip
Posted 11 hours ago
Embassy Suites by Hilton Lexington Green
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good
"Clean with decent breakfast"
Molly 1-night trip
Posted 16 hours ago
Fairfield Inn & Suites by Marriott Lexington North

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.