A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check availability on Winchester Family-Friendly Hotels

Next weekend
31 Jul - 2 Aug
In two weeks
7 Aug - 9 Aug

Our top choices for Winchester family-friendly hotels

Lobby

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,443 reviews)
  • cleanliness
    A kid-friendly getaway with indoor pool and free breakfast, just minutes from the Shenandoah Valley Discovery Museum.
The price is ₹9,657
₹10,748 total
includes taxes & fees
6 Aug - 7 Aug
Microtel Inn & Suites by Wyndham Winchester
Exterior

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Child-friendly indoor pool and activities make this hotel a perfect Winchester family retreat with premium entertainment extras.
The price is ₹8,021
₹9,217 total
includes taxes & fees
9 Aug - 10 Aug
Holiday Inn Winchester Se-Historic Gateway by IHG
Restaurant

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (916 reviews)
The price is ₹10,611
₹12,022 total
includes taxes & fees
2 Aug - 3 Aug
Hampton Inn Winchester N/Conference Center, VA
Free breakfast

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
2.5 star property
Winchester
9.0 out of 10, Wonderful, (856 reviews)
The price is ₹9,914
₹11,034 total
includes taxes & fees
9 Aug - 10 Aug
Holiday Inn Express Hotel & Suites Winchester by IHG
Interior

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (540 reviews)
  • cleanliness
    Family-friendly indoor pool oasis with premium amenities makes Winchester stays delightful for visitors of all ages.
The price is ₹7,839
₹8,882 total
includes taxes & fees
1 Aug - 2 Aug
Hilton Garden Inn Winchester
Lobby

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Family-friendly fun at this Winchester inn begins with an indoor pool, complimentary breakfast, and premium entertainment options.
The price is ₹8,421
₹9,372 total
includes taxes & fees
9 Aug - 10 Aug
Country Inn & Suites by Radisson, Winchester, VA
Standard Double Room, 2 Double Beds, Non Smoking | Blackout curtains, iron/ironing board, free cots/infant beds

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,006 reviews)
  • cleanliness
    Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodation.
The price is ₹8,947
₹9,958 total
includes taxes & fees
6 Aug - 7 Aug
Quality Inn Winchester
Fitness facility

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Family-friendly fun with outdoor pool and fitness centre, steps from Shenandoah University makes holiday dreams a reality.
The price is ₹9,700
₹10,990 total
includes taxes & fees
9 Aug - 10 Aug
Hampton Inn Winchester-University/Mall Area
Lobby sitting area

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1,006 reviews)
  • cleanliness
    Family-friendly hotel with spacious rooms offers premium entertainment and free perks near Shenandoah Valley Discovery Museum.
The price is ₹6,895
₹7,674 total
includes taxes & fees
16 Aug - 17 Aug
Sleep Inn & Suites Winchester near University
Towels, soap

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.2 out of 10, Very good, (1,007 reviews)
The price is ₹6,277
₹7,112 total
includes taxes & fees
27 Jul - 28 Jul
Motel 6 Winchester, VA
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

Breakfast included
Pool

Family-friendly hotels with free breakfast in Winchester

Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1443)
The price is ₹9,657
₹10,748 total
includes taxes & fees
6 Aug - 7 Aug
Microtel Inn & Suites by Wyndham Winchester
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Family-friendly hotels with pools in Winchester

Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1443)
The price is ₹9,657
₹10,748 total
includes taxes & fees
6 Aug - 7 Aug
Microtel Inn & Suites by Wyndham Winchester
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.
View all properties

Top Winchester Hotel Reviews

Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

10/10 Excellent
"I like the electronic check in and out and the digital key option."
Judy 2-night trip
Posted less than an hour ago
Hilton Garden Inn Dulles North

Frequently asked questions

What's Winchester like for family-friendly holidays?
The historic destination of Winchester is a good choice if you've been thinking about a trip with your children. The entertainment, soaring skyscrapers and theatres are just a few things that make this an attractive family holiday destination. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city centre.
What's the best family accommodation in Winchester?
Holiday Inn Winchester Se-Historic Gateway by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good options for your stay with the children include Microtel Inn & Suites by Wyndham Winchester and Quality Inn Winchester.
How many family hotels will I be able to find in Winchester?
Expedia has 10 family-friendly hotels and other accommodation options in Winchester.
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 2°C. Average annual precipitation for Winchester is 1172 mm.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you and the family may want to explore some interesting spots such as Winchester Little Theater, Apple Blossom Mall and Bright Box Theater. Make sure that you have lots of time for activities such as Handley Regional Library and Apple Valley Square Shopping Center.