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.

Kid 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
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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.
A hotel room with a sofa, armchair, television, kitchenette, and patterned carpet.
A bathroom with a sink, mirror, shower, and towel rack.
A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.

1. 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.
RM448
RM494 total
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn Winchester
A Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.
A modern office space with two desks, chairs, and computers.
A hotel room with two beds, a nightstand, a lamp, and a chair.
A modern bathroom with a large mirror, a sink, and a toilet.

2. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester
RM400
RM441 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Lexington East - Winchester by IHG
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
RM407
RM449 total
includes taxes & fees
20 Oct - 21 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.
RM309
RM340 total
includes taxes & fees
16 Nov - 17 Nov
Baymont by Wyndham Winchester
An indoor swimming pool with tiled flooring, orange walls, and potted plants.
A bathroom with a bathtub, a chair, and a small ottoman.
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.

5. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
RM283
RM312 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.
A lobby with a patterned carpet, seating area with chairs and a sofa, a small table, and a reception desk.
Reception
A reception area with a counter, a red door, and a 'No Smoking' sign.

6. Value Stay

Value Stay
Winchester
RM241
RM265 total
includes taxes & fees
12 Nov - 13 Nov
Value Stay
An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.
A reception area with a mural of a countryside landscape, a counter, and refrigerated display cases with snacks.
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.

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.
RM356
RM413 total
includes taxes & fees
8 Nov - 9 Nov
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A modern hotel reception area with a flat-screen TV, wooden and metal shelving, and a signboard.
A hotel room with a bed, a sofa, a desk, a chair, a TV, and a window with curtains.
An outdoor seating area with a fire feature, yellow chairs, and a colorful sofa.
A modern indoor space with a green sofa, dining tables, chairs, and a bar area with a view.

8. Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg
Lexington
RM430
RM499 total
includes taxes & fees
9 Nov - 10 Nov
Home2 Suites by Hilton Lexington Hamburg
A hotel room with a blue accent wall, a bed, a desk with a computer, a microwave, and a small refrigerator.
A bathroom with a glass shower enclosure, a toilet, and a wooden vanity with a towel rack.
A buffet with labeled containers of turkey sausage and cookies.
A coffee station with two coffee machines and a variety of coffee pods and cups.

9. Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG

Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
Lexington
RM404
RM469 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
A spacious lobby with a modern design, featuring a blue sofa, yellow armchairs, and a dining area with blue chairs.
A spacious kitchen with wooden cabinets, a large island with bar stools, and a tiled backsplash.
A modern building with a brick facade, outdoor seating area with tables and chairs, and two umbrellas providing shade.
An indoor swimming pool with clear water, a diving board, and sunlit windows.

10. Hyatt Place Lexington

Hyatt Place Lexington
Lexington
  • Splash into family fun at this Lexington hotel, where indoor pool adventures and a welcoming atmosphere create lasting memories.
RM351
RM407 total
includes taxes & fees
16 Nov - 17 Nov
Hyatt Place Lexington
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

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"It was great! Updated hotel, friendly staff and guests and good breakfast."
Ryan 1-night trip
Posted 12 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good
"Friendly staff, nice amenities, great breakfast. Rooms somewhat rundown, but overall a great stay."
Barbara J 1-night trip
Posted 12 hours ago
Fairfield Inn & Suites by Marriott Lexington North
GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Great location"
Charles 2-night trip
Posted 12 hours ago
GuestHouse Lexington
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"If you like a cottage in the woods surrounded by colorful fall leaves, this is the place. Very quiet and peaceful, close to Natural Bridge Park snd Red River Gorge."
Lyle 2-night trip
Posted 13 hours ago
Natural Bridge State Resort Park
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"Room clean and breakfast very good"
Randy 2-night trip
Posted 16 hours ago
Embassy Suites by Hilton Lexington Green
Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Great spot, nice rooms. Lovely breakfast spot. Be sure to enjoy the patio."
Michaela 3-night trip
Posted 18 hours ago
Elwood Hotel & Suites

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