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.

Family friendly Hotels in Winchester, Lexington

  • 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
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

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 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.
A hotel room with a sofa, armchair, television, kitchenette, and patterned carpet.

1. Hampton Inn Winchester

Hampton Inn Winchester
Winchester
  • Family vacation magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
P7,121
P7,850 total
includes taxes & fees
Oct 4 - Oct 5
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 room with a bed, two bedside tables, a desk, a chair, and a lamp.
A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.

2. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
P6,231
P6,869 total
includes taxes & fees
Oct 1 - Oct 2
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 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.

3. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
Winchester
  • Family-friendly hotel offers indoor swimming, free breakfast, and nearby park for all-ages adventure.
P5,342
P5,889 total
includes taxes & fees
Oct 4 - Oct 5
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 bathroom with a bathtub, a chair, and a small ottoman.

4. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
P4,740
P5,225 total
includes taxes & fees
Oct 19 - Oct 20
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.
A reception area with a counter, a red door, and a 'No Smoking' sign.

5. Value Stay

Value Stay
Winchester
P3,686
P4,063 total
includes taxes & fees
Sep 28 - Sep 29
Value Stay
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 modern hotel room with a bed, a desk, a chair, a sofa, and a large mirror.
A reception area with a mural of a countryside landscape, a counter, and refrigerated display cases with snacks.

6. 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.
P5,652
P6,560 total
includes taxes & fees
Oct 4 - Oct 5
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A hotel bathroom with a sink, mirror, towel rack, and a visible toilet.
A hotel with a lobby, a parking lot, and a building with a brown roof.
A hotel room with two beds, a TV, a desk with a chair, a window with curtains, and a door.
A hotel reception area with a reception desk, a large window, and a doormat with the hotel's logo.

7. Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
Lexington
  • Family-friendly escape in Lexington offers comfortable rooms, convenient breakfast options, and easy access to local attractions.
P4,036
P4,684 total
includes taxes & fees
Oct 4 - Oct 5
Days Inn Lexington SE/Hamburg
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.
An indoor swimming pool with clear water, a diving board, and sunlit windows.
A modern building with a brick facade, outdoor seating area with tables and chairs, and two umbrellas providing shade.

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.
P6,310
P7,324 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Place Lexington
A hotel lobby with blue walls, a seating area with blue chairs, a bar, and artwork on the walls.
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 hotel room with two beds, a bathroom, and a hallway.
An indoor swimming pool with a lifeguard station, poolside chairs, and a clear 3 FT depth marking.

9. 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.
P4,195
P4,869 total
includes taxes & fees
Sep 28 - Sep 29
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

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Nice clean room great location"
Brian 1-night trip
Posted 23 hours ago
Hyatt Regency Lexington
Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

8/10 Good
"Clean rooms, helpful staff"
Karen 1-night trip
Posted 1 day ago
Microtel Inn by Wyndham Lexington
Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Such a great boutique hotel with a lot of character and a wonderful restaurant as well. We really enjoyed our stay! Staff was extremely helpful."
Sara 1-night trip
Posted 2 days ago
Elwood Hotel & Suites
GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"Good price and value. Breakfast is modest but adequate. The rooms are clean and staff is friendly. The shampoo and conditioner bottles were empty."
Petrina 1-night trip
Posted 2 days ago
GuestHouse Lexington
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"The front desk clerk and staff were warm, inviting, friendly, and fun to interact with. The room was just what I needed for one night. The shower pressure was one of the best I've experienced in any hotel."
Roshanda 1-night trip
Posted 4 days ago
Fairfield Inn & Suites by Marriott Lexington North

Frequently asked questions

What's Winchester like for family-friendly vacations?
The welcoming destination of Winchester is a great choice if you've been thinking about a vacation with the kids. The excursions, football games, and cafes are just some of the things that make this an attractive family vacation spot. Arrange a flight into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) from the city center.
What's the best place to stay for families 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 vacation in Winchester?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you might want to round up the kiddos and make time to see interesting attractions such as Clark County Public Library and Lexington Sporting Club Youth Complex. Make sure you have lots of time for activities like Hamburg Pavilion and Hamburg Place.

Explore a world of travel with Expedia