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

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 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.
A hotel room with a sofa, armchair, television, kitchenette, and patterned carpet.

1. Hampton Inn Winchester

Hampton Inn Winchester
Winchester
  • Family holiday magic at Hampton Inn Winchesterโ€”splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
S$155
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 modern bathroom with a granite countertop sink, a white toilet, a bathtub, and a large mirror.
A hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.
A lobby with two armchairs, a reception desk, and a chandelier.

2. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
S$141
includes taxes & fees
13 Oct - 14 Oct
Best Western Winchester Hotel
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 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.

3. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester
S$140
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Lexington East - Winchester by IHG
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 hotel dining area with a coffee station, a clock, and large windows offering a view of the outside.
A hotel room with two beds, a sofa, a desk, and a window with blinds.

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.
S$108
includes taxes & fees
1 Nov - 2 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.
A lobby with a patterned carpet, seating area with chairs and a sofa, a small table, and a reception desk.
Reception
Bathroom

5. Value Stay

Value Stay
Winchester
S$79
includes taxes & fees
9 Nov - 10 Nov
Value Stay
An indoor swimming pool with tiled flooring, orange walls, and potted plants.
A hotel room with a large bed, a bedside table with a lamp, and a telephone.
A spacious dining area with multiple tables and chairs, a kitchenette in the background, and large windows allowing natural light.
A waiting area with blue sofas and a brown ottoman, a reception desk, and a door leading to a hallway.

6. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
S$110
includes taxes & fees
2 Nov - 3 Nov
Comfort Inn Winchester
An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.
A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.
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.

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.
S$130
includes taxes & fees
11 Oct - 12 Oct
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A spacious lobby with a modern design, featuring a blue sofa, yellow armchairs, and a dining area with blue chairs.
An indoor swimming pool with clear water, a diving board, and sunlit windows.
A hotel room with a large bed, a wooden nightstand, a lamp, and a sofa with a cushion.
A spacious kitchen with wooden cabinets, a large island with bar stools, and a tiled backsplash.

8. 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.
S$128
includes taxes & fees
9 Nov - 10 Nov
Hyatt Place Lexington
A pool table in a modern lounge area with a bar and seating.
A modern food court with a variety of food stalls, a coffee station, and a seating area with a view of the outside.
An outdoor seating area with two sofas, a round table, and a planter with flowers.
A modern hotel reception area with a curved counter, two monitors, and a view of the lobby.

9. Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
Liberty Area
S$122
includes taxes & fees
8 Nov - 9 Nov
Tru By Hilton Lexington Hamburg
A hotel lobby with blue walls, a seating area with blue chairs, a bar, and artwork on the walls.
An indoor swimming pool with a lifeguard station, poolside chairs, and a clear 3 FT depth marking.
A spacious lobby with a high ceiling, large windows, and a blue accent wall. There are multiple seating areas with chairs and tables, and a television mounted on the wall.
A guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.

10. GuestHouse Lexington

GuestHouse Lexington
Lexington
  • Splash into family fun with a heated indoor pool, premium entertainment, and thoughtful kid-friendly amenities at this Lexington retreat.
S$100
includes taxes & fees
19 Oct - 20 Oct
GuestHouse 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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Clean, helpful staff and a nice restaurant onsite."
Laura 2-night trip
Posted less than an hour ago
Elwood Hotel & Suites
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Great property! Beautiful setting!"
Lillian 2-night trip
Posted 5 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

10/10 Excellent
"Nice clean and comfortable"
Charyl 1-night trip
Posted 21 hours ago
Quality Inn Lexington -Horse Park
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Staff was friendly. Enjoyed the restaurant and Trails End Lounge. Great location for many trails and Skylift as well as Restaurants nearby. Nice view from balcony; peaceful."
Ellen 2-night trip
Posted 1 day ago
Natural Bridge State Resort Park
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"It was nice stay"
IRFAN 2-night trip
Posted 2 days ago
Marriott Lexington Griffin Gate Golf Resort & Spa

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 22ยฐC, while the coldest months are January and February, with an average of 4ยฐC. 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.

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