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 Hotels

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 hotel room with two beds, a nightstand, a lamp, and a chair.
A modern office space with two desks, chairs, and computers.

1. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester
₩141,881
₩156,409 total
includes taxes & fees
Nov 4 - Nov 5
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 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.
A hotel room with a sofa, armchair, television, kitchenette, and patterned carpet.

2. 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.
₩158,144
₩174,339 total
includes taxes & fees
Nov 1 - Nov 2
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.

3. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
₩133,502
₩147,172 total
includes taxes & fees
Oct 11 - Oct 12
Best Western Winchester Hotel
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 Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.

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.
₩102,395
₩112,889 total
includes taxes & fees
Nov 1 - Nov 2
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 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.

5. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
₩104,671
₩115,388 total
includes taxes & fees
Nov 2 - Nov 3
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 reception area with a counter, a red door, and a 'No Smoking' sign.
Bathroom
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
₩78,972
₩87,057 total
includes taxes & fees
Oct 19 - Oct 20
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 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.

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.
₩121,094
₩140,554 total
includes taxes & fees
Oct 18 - Oct 19
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A restaurant with booths and tables, a stone pillar, and a TV screen.
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.
A hotel room with a bed, desk, chair, and a window with a view of buildings.

8. 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.
₩131,173
₩152,252 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Lexington - Hamburg by IHG
A large indoor swimming pool with a tiled floor, surrounded by large windows and a seating area with tables and chairs.
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.
A hotel room with two beds, a desk, a chair, and a large window with a view of trees.
A modern hotel lobby with a long communal table, blue and orange seating, a coffee station, and a large wooden door.

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

Holiday Inn Express Lexington - Horse Park Area by IHG
Lexington
₩124,481
₩144,485 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Express Lexington - Horse Park Area by IHG
An outdoor seating area with modern furniture, planters, and a building in the background.
A modern hotel room with two beds, a small round table, a lamp, and a painting on the wall.
A potted plant next to a grey sofa with a yellow and white throw blanket.
A building with a large mural of a child painting a tree, the name 'Elwood' displayed prominently, and a symmetrical facade with a central entrance.

10. Elwood Hotel & Suites

Elwood Hotel & Suites
Lexington
  • Experience university adventures at Elwood Hotel, where family-friendly amenities meet comfort during your Lexington getaway.
₩148,172
₩171,984 total
includes taxes & fees
Nov 2 - Nov 3
Elwood Hotel & Suites
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
"Beautiful, secluded, clean room"
DARRIN 2-night trip
Posted 17 hours ago
Elwood Hotel & Suites
Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

8/10 Good
"Overall stay was pretty good. Staff seemed to be rushing us. Gentleman was saying he was already supposed to be gone, so not very professional. Breakfast was good. Would stay again."
Shirley 1-night trip
Posted 21 hours ago
Comfort Inn & Suites Lexington - Hamburg I-75
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

8/10 Good
"Great location and comfortable beds. Bathroom needed maintenance"
Alanna 1-night trip
Posted 22 hours ago
Quality Inn Lexington -Horse Park
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Great stay- spacious rooms. Clean and well stocked hot breakfast!"
Heather 1-night trip
Posted 2 days ago
Embassy Suites by Hilton Lexington/UK Coldstream
Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Close to multiple trails and restaurants."
Curtis 2-night trip
Posted 2 days ago
Natural Bridge State Resort Park
Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Xxxxxxcxxxxxxxxxxxxxxxxxxxxx"
John 2-night trip
Posted 2 days ago
Hyatt Regency Lexington
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good
"Good stay room was clean an comfortable front desk staff were friendly and very accommodating"
Dave 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Lexington North
Comfort Inn Winchester

Comfort Inn Winchester

10/10 Excellent
"Everyone was super sweet the room was clean and breakfast was decent just wish the pool had been in service"
Brittany 3-night trip
Posted 12 days ago
Comfort Inn Winchester

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 Hamburg Pavilion. Make sure you have lots of time for activities like Hamburg Place and Claiborne Farm.

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