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
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

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 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.

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.
฿3,726
฿4,107 total
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn Winchester
A swimming pool with wooden walls and large windows offering views of greenery.
A hotel dining area with a coffee station, a clock, and large windows offering a view of the outside.
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 room with two beds, a sofa, a desk, and a window with blinds.

2. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
Winchester
  • Family-friendly hotel offers indoor swimming, free breakfast, and nearby park for all-ages adventure.
฿2,471
฿2,725 total
includes taxes & fees
30 Aug - 31 Aug
Baymont by Wyndham Winchester
A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.
A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.
A lobby with two armchairs, a reception desk, and a chandelier.
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
฿2,795
฿3,081 total
includes taxes & fees
31 Aug - 1 Sept
Best Western Winchester Hotel
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.

4. Value Stay

Value Stay
Winchester
฿1,929
฿2,126 total
includes taxes & fees
28 Aug - 29 Aug
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 spacious dining area with multiple tables and chairs, a kitchenette in the background, and large windows allowing natural light.
A bathroom with a bathtub, a chair, and a small ottoman.

5. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
฿2,751
฿3,032 total
includes taxes & fees
20 Sept - 21 Sept
Comfort Inn Winchester
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 multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.
A lobby with a sofa, armchairs, a fireplace, a TV, and a patterned rug.

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.
฿2,957
฿3,433 total
includes taxes & fees
31 Aug - 1 Sept
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A hotel bathroom with a sink, mirror, towel rack, and a visible toilet.
A hotel room with two beds, a TV, a desk with a chair, a window with curtains, and a door.
A hotel with a lobby, a parking lot, and a building with a brown roof.
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.
฿1,971
฿2,288 total
includes taxes & fees
1 Sept - 2 Sept
Days Inn Lexington SE/Hamburg
A hotel lobby with blue walls, a seating area with blue chairs, a bar, and artwork on the walls.
A hotel room with two beds, a bathroom, and a hallway.
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.

8. 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.
฿2,389
฿2,773 total
includes taxes & fees
30 Aug - 31 Aug
GuestHouse Lexington
A spacious living room with a blue sofa, a grey armchair, and a fireplace.
A modern dining area with a long wooden table and blue cushioned chairs.
A bathroom with a toilet, sink, mirror, and handrails.
A fitness center with treadmills, a mirrored wall, a clock, and a phone on a shelf.

9. Comfort Inn Lexington I-75

Comfort Inn Lexington I-75
Lexington
฿2,332
฿2,707 total
includes taxes & fees
27 Sept - 28 Sept
Comfort Inn Lexington I-75
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

Natural Bridge State Resort Park

Natural Bridge State Resort Park

8/10 Good
"Excellent location with easy access to a lot of the trails in the area and a short drive to Auxiers Ridge trails. The rooms could use some updating as they start to show regular aging and cleaning could be more in depth and reaching all surfaces. every staff is extremely nice and helpful. overall a great quality to price ratio."
Roger 3-night trip
Posted 7 hours ago
Natural Bridge State Resort Park
Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Classy and quaint. Superb restaurant too!"
Dale 2-night trip
Posted 9 hours ago
Elwood Hotel & Suites
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

10/10 Excellent
"The property and our room was extremely clean and nice, the bed super comfortable. The food & drinks at the Rackhouse was amazing especially the Fried Chicken! Highly recommended!! However, my only complaint is with the bathroom, there’s no place to put your things, no shelf space and there’s plenty of room for it. Oh and having to pay for waters?! For the cost of the room water should be free!"
Michelle 2-night trip
Posted 14 hours ago
The Campbell House Lexington, Curio Collection by Hilton
GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"Close to everything the staff was excellent clean and quiet rooms"
Michael 1-night trip
Posted 21 hours ago
GuestHouse Lexington
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"Everything was great"
wendle 2-night trip
Posted 2 days ago
Marriott Lexington Griffin Gate Golf Resort & Spa
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

10/10 Excellent
"Very accommodating unlike some other hotels I am disabled asked for first floor and they did accommodate me. Pool was clean room was clean. I travel from Arkansas to Pennsylvania for 1 week every month this is my 2nd month staying there I will definitely continue to use this hotel."
Jason 1-night trip
Posted 2 days ago
Baymont by Wyndham Winchester
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"Great stay and the breakfast had an amazing variety. Highly recommend."
Catherine 1-night trip
Posted 3 days ago
Embassy Suites by Hilton Lexington Green
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"This hotel featured well appointed roomy suites and a great breakfast and a bar with great food and drinks."
Dorothy 1-night trip
Posted 3 days ago
Embassy Suites by Hilton Lexington/UK Coldstream
Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

8/10 Good
"Close to everything clean room nice parking staff was excellent"
Michael 1-night trip
Posted 3 days ago
Microtel Inn by Wyndham Lexington

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 Lexington Sporting Club Youth Complex. Make sure that you have lots of time for activities such as Hamburg Pavilion and Hamburg Place.

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