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
Aug 17 - Aug 18
Tomorrow
Aug 18 - Aug 19
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Winchester family-friendly hotels

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

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.
NT$3,126
NT$3,446 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn Winchester
Indoor pool
Lobby
Suite, 2 Queen Beds | Desk, laptop workspace, iron/ironing board, WiFi (free)
Free daily continental breakfast

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.
NT$2,422
NT$2,670 total
includes taxes & fees
Aug 18 - Aug 19
Baymont by Wyndham Winchester
Free daily full breakfast
Standard Room, 2 Double Beds, Non Smoking, Kitchenette | Bathroom | Combined shower/tub, hair dryer, towels
Exterior
Standard Room, 2 Double Beds, Non Smoking, Kitchenette | Desk, iron/ironing board, rollaway beds (surcharge), bed sheets

3. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
NT$2,739
NT$3,019 total
includes taxes & fees
Aug 23 - Aug 24
Best Western Winchester Hotel
Suite, 1 King Bed, Hot Tub | WiFi (free), bed sheets
Lobby
Reception
Reception

4. Value Stay

Value Stay
Winchester
NT$1,890
NT$2,084 total
includes taxes & fees
Aug 20 - Aug 21
Value Stay
Pool
Breakfast area
Standard Room, 2 Queen Beds, Non Smoking | Desk, iron/ironing board, WiFi (free), bed sheets
Lobby

5. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
NT$2,451
NT$2,702 total
includes taxes & fees
Sep 13 - Sep 14
Comfort Inn Winchester
Indoor pool, sun loungers
Lobby
Deluxe Room, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Impaired Accessible) | Premium bedding, pillowtop beds, desk, blackout drapes
Exterior

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.
NT$2,898
NT$3,364 total
includes taxes & fees
Aug 23 - Aug 24
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Combined shower/tub, free toiletries, towels
Desk, iron/ironing board, cribs (free), rollaway beds (surcharge)
Exterior
Business center

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.
NT$1,932
NT$2,242 total
includes taxes & fees
Aug 24 - Aug 25
Days Inn Lexington SE/Hamburg
Daily cooked-to-order breakfast for a fee
Meeting facility
Fitness facility
Bar (on property)

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.
NT$2,915
NT$3,384 total
includes taxes & fees
Sep 15 - Sep 16
Holiday Inn Lexington - Hamburg by IHG
Lobby
Free daily self-serve breakfast
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
NT$2,451
NT$2,844 total
includes taxes & fees
Aug 24 - Aug 25
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

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

8/10 Good
"Great hotel. Great location. Nice pool. Staff was friendly and helpful. Hotel was clean. The only issue I have is that there is a $15 per night parking fee which I wasn't made aware of until I checked in. There really is no reason to charge $15 and night for parking. It's not like somebody is checking the cars to see if they belong there or not. There were plenty of spots."
Christopher 4-night trip
Posted 1 hour ago
DoubleTree Suites by Hilton Hotel Lexington
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

8/10 Good
"They seem very short staffed. The tavern was super busy. I tried to eat dinner and finally just went back to my room as I didn’t get waited on but lunch was very good. The rooms are very nicely decorated and roomy but I noticed that the bath tub plug was broken so I couldn’t have a bath and there is no refrigerator in the room nor ice machines so you have to ask for ice from the restaurant. The room smelt very musty."
Clare 3-night trip
Posted 1 hour ago
The Campbell House Lexington, Curio Collection by Hilton
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Clean"
Jaime 1-night trip
Posted 2 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream
Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Nice, unique spot close to UK. Would stay there again."
Nathan 2-night trip
Posted 3 hours ago
Elwood Hotel & Suites
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"The staff was so friendly and helpful.Breakfast was great and the orange juice was delicious! We will definitely be back! Not to mention the comvience of Cracker Barrel"
Kimberly 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.

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