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
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sep - 6 Sep

Our top choices for Winchester family-friendly hotels

Room, 1 King Bed, Accessible | Select Comfort beds, in-room safe, desk, laptop workspace
Room, Accessible, Non Smoking | Bathroom shower
Reception
Suite, 1 King Bed, Non Smoking | Select Comfort beds, in-room safe, desk, laptop workspace

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.
AED 389
AED 428 total
includes taxes & fees
30 Aug - 31 Aug
Hampton Inn Winchester
Free daily full breakfast
Exterior
Lobby sitting area
Standard Room, 2 Double Beds, Non Smoking, Kitchenette | Bathroom | Combined shower/tub, hair dryer, towels

2. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
AED 314
AED 346 total
includes taxes & fees
27 Aug - 28 Aug
Best Western Winchester Hotel
Indoor pool
Free daily continental breakfast
Lobby
Lobby

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.
AED 278
AED 306 total
includes taxes & fees
23 Aug - 24 Aug
Baymont by Wyndham Winchester
Suite, 1 King Bed, Hot Tub | WiFi (free), bed sheets
Free toiletries, towels, soap, shampoo
Lobby
Reception

4. Value Stay

Value Stay
Winchester
AED 217
AED 239 total
includes taxes & fees
23 Aug - 24 Aug
Value Stay
Pool
Desk, iron/ironing board, WiFi (free), bed sheets
Standard Room, 2 Queen Beds, Non Smoking | Desk, iron/ironing board, WiFi (free), bed sheets
Lobby

5. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
AED 281
AED 310 total
includes taxes & fees
13 Sep - 14 Sep
Comfort Inn Winchester
Combined shower/tub, hair dryer, towels, soap
Interior
Exterior
Interior

6. Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Winchester
AED 891
AED 1,217 total
includes taxes & fees
30 Aug - 31 Aug
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Indoor pool, sun loungers
Exterior
Lobby
Deluxe Room, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Impaired Accessible) | Premium bedding, pillowtop beds, desk, blackout drapes

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.
AED 317
AED 368 total
includes taxes & fees
24 Aug - 25 Aug
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Combined shower/tub, free toiletries, towels
Business center
Desk, iron/ironing board, cribs (free), rollaway beds (surcharge)
Exterior

8. 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.
AED 221
AED 257 total
includes taxes & fees
23 Aug - 24 Aug
Days Inn Lexington SE/Hamburg
Lobby
Premium bedding, down comforters, desk, laptop workspace
Fitness facility
Standard Room, 2 Queen Beds | Premium bedding, down comforters, desk, laptop workspace

9. Comfort Inn Lexington I-75

Comfort Inn Lexington I-75
Lexington
AED 264
AED 307 total
includes taxes & fees
30 Aug - 31 Aug
Comfort Inn Lexington I-75
Daily cooked-to-order breakfast for a fee
Fitness facility
Exterior
Meeting facility

10. 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.
AED 320
AED 371 total
includes taxes & fees
20 Sep - 21 Sep
Holiday Inn Lexington - Hamburg by IHG
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

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good
"Have a very good stay , everyone was very helpful!!"
Bea 1-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Lexington North
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"Loved the hotel overall"
Brad 1-night trip
Posted 1 hour ago
Embassy Suites by Hilton Lexington Green
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"It was absolutely beautiful the staff is what made the stay a five star. ⭐️ They greeted us with happy anniversary placed roses in the room and gave us complimentary tickets. Best staff ever !"
Justin 1-night trip
Posted 1 day ago
Embassy Suites by Hilton Lexington/UK Coldstream
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

8/10 Good
"Very nice hotel and well situated close to Kentucky campus. AC in room was finicky and the bar was a bit small and constantly packed with only one bartender to manage. No fridge in room and no free buffet. Other than that it wa fine."
James 2-night trip
Posted 2 days ago
The Campbell House Lexington, Curio Collection by Hilton
Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Great place to stay for moving our daughter in to UK. Convenient location, comfortable and clean room and hotel, friendly and helpful staff."
Jenny 2-night trip
Posted 3 days ago
Elwood Hotel & Suites

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.