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

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug

Our top choices for Winchester family-friendly hotels

Indoor pool

1. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (832 reviews)
  • cleanliness
    Family-friendly hotel offers indoor swimming, free breakfast, and nearby park for all-ages adventure.
The price is ₹7,212
₹7,951 total
includes taxes & fees
2 Aug - 3 Aug
Baymont by Wyndham Winchester
Free daily full breakfast

2. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,002 reviews)
The price is ₹8,155
₹8,990 total
includes taxes & fees
12 Aug - 13 Aug
Best Western Winchester Hotel
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets

3. Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (165 reviews)
The price is ₹5,628
₹6,204 total
includes taxes & fees
2 Aug - 3 Aug
Value Stay
Lobby

4. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (477 reviews)
  • cleanliness
    Family holiday magic at Hampton Inn Winchester—splash in the seasonal pool, enjoy free breakfast, and explore parks nearby.
The price is ₹10,873
₹11,986 total
includes taxes & fees
16 Aug - 17 Aug
Hampton Inn Winchester
Pool

5. Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (377 reviews)
The price is ₹7,460
₹8,224 total
includes taxes & fees
30 Aug - 31 Aug
Comfort Inn Winchester
Indoor pool, pool loungers

6. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,180 reviews)
  • cleanliness
    Create unforgettable family memories at a hotel with an indoor pool, premium entertainment, and complimentary breakfast included.
The price is ₹8,630
₹10,017 total
includes taxes & fees
16 Aug - 17 Aug
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Combined shower/bathtub, free toiletries, towels

7. Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,000 reviews)
  • cleanliness
    Family-friendly escape in Lexington offers comfortable rooms, convenient breakfast options, and easy access to local attractions.
The price is ₹5,752
₹6,677 total
includes taxes & fees
9 Aug - 10 Aug
Days Inn Lexington SE/Hamburg
Lobby

8. Comfort Inn Lexington I-75

Comfort Inn Lexington I-75
2.5 star property
Lexington
7.4 out of 10, Good, (798 reviews)
The price is ₹6,712
₹7,790 total
includes taxes & fees
23 Aug - 24 Aug
Comfort Inn Lexington I-75
Indoor pool

9. Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
2.5 star property
Lexington
8.6 out of 10, Excellent, (1,002 reviews)
The price is ₹8,135
₹9,442 total
includes taxes & fees
16 Aug - 17 Aug
Hampton Inn I-75 Lexington/Hamburg Area
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"The restaurant at the hotel was amazing. The food was outstanding.! I ate there four times and it was great every time!"
Scott 2-night trip
Posted 1 hour ago
Elwood Hotel & Suites

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 Hamburg Pavilon. Make sure that you have lots of time for activities such as Hamburg Place and Claiborne Farm.