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.

Search Family-Friendly Hotels in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Family-Friendly Hotels

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 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 kitchen area with a coffee machine, a fruit display, and a 'GOOD MORNING' sign on the wall.
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
Rp1.709.240
Rp1.884.267 total
includes taxes & fees
19 Nov - 20 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 reception desk with a 'Manager On Duty' sign, framed pictures on the wall, and a 'Welcome to Winchester' sign.
A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.
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.
Rp2.129.299
Rp2.347.339 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Winchester
A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.
A modern bathroom with a granite countertop sink, a white toilet, a bathtub, and a large mirror.
A lobby with two armchairs, a reception desk, and a chandelier.
A hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
Rp1.623.598
Rp1.789.854 total
includes taxes & fees
2 Nov - 3 Nov
Best Western Winchester Hotel
A swimming pool with wooden walls and large windows offering views of greenery.
A Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.
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.
Rp1.360.195
Rp1.499.479 total
includes taxes & fees
2 Nov - 3 Nov
Baymont by Wyndham Winchester
An indoor swimming pool with tiled flooring, orange walls, and potted plants.
A spacious dining area with multiple tables and chairs, a kitchenette in the background, and large windows allowing natural light.
A hotel room with a large bed, a bedside table with a lamp, and a telephone.
A waiting area with blue sofas and a brown ottoman, a reception desk, and a door leading to a hallway.

5. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
Rp1.257.821
Rp1.386.623 total
includes taxes & fees
16 Nov - 17 Nov
Comfort Inn 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.
Reception
A reception area with a counter, a red door, and a 'No Smoking' sign.
A lobby with a patterned carpet, seating area with chairs and a sofa, a small table, and a reception desk.

6. Value Stay

Value Stay
Winchester
Rp1.061.528
Rp1.170.200 total
includes taxes & fees
11 Nov - 12 Nov
Value Stay
An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.
A lobby with a sofa, armchairs, a fireplace, a TV, and a patterned rug.
A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.
A modern hotel room with a bed, a desk, a chair, a sofa, and a large mirror.

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

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Lexington
  • Create unforgettable family memories at a hotel with an indoor pool, premium entertainment, and complimentary breakfast included.
Rp1.571.518
Rp1.824.060 total
includes taxes & fees
25 Oct - 26 Oct
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.
A multi-story hotel with a curved entrance canopy, large windows, and a modern design.
A hotel room with two beds, a desk, a chair, and a large window with a view of trees.
A modern dining area with a central white table surrounded by blue chairs, a flat-screen TV mounted on the wall, and large windows offering a view of the outside.

8. Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG
Lexington
Rp1.567.914
Rp1.819.878 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Express Lexington - Horse Park Area by IHG
A restaurant with booths and tables, a stone pillar, and a TV screen.
A hotel room with a bed, desk, chair, and a window with a view of buildings.
A bar area with a marble wall, shelves of liquor bottles, and a display case with pastries.
A hotel room with a bed, bedside tables, a desk, a chair, and a window with a view.

9. Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
Lexington
  • Kid-friendly adventures await with indoor pool and firepit activities at this well-appointed Lexington hotel with spacious rooms.
Rp1.495.826
Rp1.736.205 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Lexington - Hamburg by IHG
A modern hotel reception area with a flat-screen TV, wooden and metal shelving, and a signboard.
An indoor swimming pool with clear water, surrounded by yellow chairs and potted plants.
A modern indoor space with a green sofa, dining tables, chairs, and a bar area with a view.
An outdoor seating area with a fire feature, yellow chairs, and a colorful sofa.

10. Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg
Lexington
Rp1.976.112
Rp2.293.674 total
includes taxes & fees
22 Nov - 23 Nov
Home2 Suites by Hilton Lexington Hamburg
View all properties

Choose what matters most at family-friendly hotels in Winchester

Pool
Breakfast included
All-inclusive
4 stars
5 stars

Top Winchester Hotel Reviews

Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

10/10 Excellent
"Stayed here 3 nights. Was very enjoyable ! The room was very clean and the staff was very helpful. We were on the I-75 side of the hotel the first night . It was very noisy with all the trucks on I-75 very close by. The noise level was 75db. They moved us across the hall and was perfect ! We would stay here again!"
Gene 2-night trip
Posted less than an hour ago
Comfort Inn & Suites Lexington - Hamburg I-75
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Comfortable hotel - a cut above the average chain hotels"
Leslie 1-night trip
Posted 6 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Great"
Hana 2-night trip
Posted 11 hours ago
Natural Bridge State Resort Park
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Great hosts"
Robert 3-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Lexington North
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 3 days ago
Embassy Suites by Hilton Lexington Green

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.

Explore a world of travel with Expedia