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

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Winchester family-friendly hotels

Room, 2 Queen Beds, Non Smoking | Free WiFi, bed sheets

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (158 reviews)
The price is Rp1.056.513
Rp1.164.671 total
includes taxes & fees
1 Aug - 2 Aug
Value Stay
Reception

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,001 reviews)
The price is Rp1.530.869
Rp1.687.630 total
includes taxes & fees
27 Jul - 28 Jul
Best Western Winchester Hotel
Desk, laptop workspace, iron/ironing board, free WiFi

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (817 reviews)
  • cleanliness
    Family-friendly hotel offers indoor swimming, free breakfast, and nearby park for all-ages adventure.
The price is Rp1.353.769
Rp1.492.395 total
includes taxes & fees
26 Jul - 27 Jul
Baymont by Wyndham Winchester
Breakfast area

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (370 reviews)
The price is Rp1.161.448
Rp1.280.380 total
includes taxes & fees
26 Jul - 27 Jul
Comfort Inn Winchester
Snack bar

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (471 reviews)
  • cleanliness
    Family holiday magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
The price is Rp2.378.766
Rp2.622.352 total
includes taxes & fees
29 Jul - 30 Jul
Hampton Inn Winchester
Free daily buffet breakfast

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,177 reviews)
The price is Rp1.844.421
Rp2.140.819 total
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Express Lexington Horse Park Area by IHG
Lobby

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,003 reviews)
  • cleanliness
    Family-friendly escape in Lexington offers comfortable rooms, convenient breakfast options, and easy access to local attractions.
The price is Rp862.382
Rp1.000.906 total
includes taxes & fees
12 Jul - 13 Jul
Days Inn Lexington SE/Hamburg
Suite, 1 King Bed with Sofa bed, Non Smoking, Hot Tub | Jetted bathtub

Comfort Suites Richmond

Comfort Suites Richmond
2.5 star property
Richmond
7.4 out of 10, Good, (762 reviews)
  • cleanliness
    Comfort Suites Richmond offers an indoor pool paradise where families can swim, play, and make lasting holiday memories together.
The price is Rp870.280
Rp959.397 total
includes taxes & fees
28 Jul - 29 Jul
Comfort Suites Richmond
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at family-friendly hotels in Winchester

Pool
Breakfast included

Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"Embassy Suites lived up to its reputation. Nice room, evening food and drinks and complimentary breakfast. I would stay here again!"
Brett 1-night trip
Posted 11 hours ago
Embassy Suites by Hilton Lexington/UK Coldstream

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 Pavilon and Hamburg Place.