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
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Winchester family-friendly hotels

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$3,625
NT$3,996 total
includes taxes & fees
Oct 4 - Oct 5
Hampton Inn Winchester

2. Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester
NT$3,172
NT$3,497 total
includes taxes & fees
Sep 22 - Sep 23
Best Western Winchester Hotel

3. Value Stay

Value Stay
Winchester
NT$1,877
NT$2,069 total
includes taxes & fees
Sep 18 - Sep 19
Value Stay

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.
NT$2,538
NT$2,798 total
includes taxes & fees
Sep 23 - Sep 24
Baymont by Wyndham Winchester

5. Comfort Inn Winchester

Comfort Inn Winchester
Winchester
NT$2,275
NT$2,508 total
includes taxes & fees
Oct 15 - Oct 16
Comfort Inn Winchester

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$2,877
NT$3,340 total
includes taxes & fees
Sep 21 - Sep 22
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

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$2,024
NT$2,350 total
includes taxes & fees
Sep 27 - Sep 28
Days Inn Lexington SE/Hamburg

8. Comfort Inn Lexington I-75

Comfort Inn Lexington I-75
Lexington
NT$2,261
NT$2,625 total
includes taxes & fees
Oct 18 - Oct 19
Comfort Inn Lexington I-75

9. 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.
NT$3,217
NT$3,734 total
includes taxes & fees
Sep 21 - Sep 22
Hyatt Place 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 Place Lexington

Hyatt Place Lexington

8/10 Good
"I thought it was ridiculous that they wanted a $25 fee for checking in an hour early when the hotels parking lot was empty. i thought that was pretty tacky."
Greg 1-night trip
Posted 2 hours ago
Hyatt Place Lexington
Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"We had a wonderful stay. Everyone we encountered was very friendly and polite. Check in a breeze , the bartender amazing, our room perfect. Would definitely recommend it."
Beth 1-night trip
Posted 21 hours ago
Elwood Hotel & Suites
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"Room was beautiful! Breakfast was great, we especially liked the idea of an omelette made while we waited. The snacks in the room were a welcome surprise. We really enjoyed our stay!"
Robert 4-night trip
Posted 23 hours ago
Embassy Suites by Hilton Lexington Green
GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Very clean Staff was very friendly and helpful"
Clifton 1-night trip
Posted 2 days ago
GuestHouse Lexington
Days Inn & Suites by Wyndham Lexington

Days Inn & Suites by Wyndham Lexington

10/10 Excellent
"The grounds needed some cleaning. Room was great."
Ronda 1-night trip
Posted 2 days ago
Days Inn & Suites by Wyndham Lexington
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"Room was clean, restraunt had amazing food, staff was great"
Larry 1-night trip
Posted 3 days ago
Marriott Lexington Griffin Gate Golf Resort & Spa
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"The breakfast was delish!!! Lots of options and very fresh."
Peggy 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Lexington North
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

8/10 Good
"Pool didn’t look clean and the toilet in my room didn’t flush properly but everything else was 100% I would stay again"
Murphy 3-night trip
Posted 4 days ago
Embassy Suites by Hilton Lexington/UK Coldstream

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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