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Check availability on Winchester Family-Friendly Hotels

Our top choices for Winchester family-friendly hotels

Front of property – evening/night

Skyland

Skyland
2.0 star property
Luray
8.8 out of 10, Excellent, (1,006 reviews)
"Not only does it offer a safe environment for families but it is serene for individuals too."
United States
Anna
The price is ฿5,885
฿7,013 total
includes taxes & fees
25 May - 26 May
Skyland
Lobby

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,009 reviews)
"I enjoy staying at this hotel. Pet friendly for sure. Gives you free breakfast. I have no complains about the service or the hotel. I have one suggestion please fix the bending machine. "
United States
Rene M
The price is ฿2,243
฿2,497 total
includes taxes & fees
20 May - 21 May
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Lobby

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
8.8 out of 10, Excellent, (1,009 reviews)
  • cleanliness
    Outdoor adventures and kid-friendly comforts await near historic Harpers Ferry with premium TV, cots, and nature trails.
"Great little hotel in Harper’s ferry. Stayed new years evenbecasue the hotel i usually stay at was booked. Friendly staff. Clean rooms. Nice amenities. Fair prices. Nothing else i would need from a hotel!"
United States
Billie
The price is ฿3,308
฿3,705 total
includes taxes & fees
25 May - 26 May
Quality Inn Harpers Ferry - Charles Town
Room, 1 King Bed, Non Smoking | Iron/ironing board, free WiFi

Quality Inn Shepherdstown

Quality Inn Shepherdstown
2.5 star property
Shepherdstown
8.0 out of 10, Very good, (236 reviews)
  • cleanliness
    Family-friendly Shepherdstown retreat offers complimentary breakfast, free cots, and easy access to the historic C&O canal.
"Room was clean and beds comfy. Staff friendly Location Hotel was greatthe Hotel "
United States
Bianca
The price is ฿2,985
฿3,343 total
includes taxes & fees
31 May - 1 Jun
Quality Inn Shepherdstown
Lobby

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,465 reviews)
  • cleanliness
    A kid-friendly getaway with indoor pool and free breakfast, just minutes from the Shenandoah Valley Discovery Museum.
"perfect for my family!"
United States
David
The price is ฿3,095
฿3,368 total
includes taxes & fees
24 May - 25 May
Microtel Inn & Suites by Wyndham Winchester
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, (1,009 reviews)
  • cleanliness
    Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodation.
"He stayed here multiple times. Pool area is great to sit and read or swim. Breakfast was very good and the staff was extremely friendly. "
United States
Margaret
The price is ฿2,965
฿3,226 total
includes taxes & fees
31 May - 1 Jun
Quality 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, (1,004 reviews)
  • cleanliness
    Family-friendly fun at this Winchester inn begins with an indoor pool, complimentary breakfast, and premium entertainment options.
"Stayed with family."
United States
scott
The price is ฿3,056
฿3,325 total
includes taxes & fees
9 Jun - 10 Jun
Country Inn & Suites by Radisson, Winchester, VA
Room, 1 King Bed, Accessible, Non Smoking | Premium bedding, pillow-top beds, in-room safe, individually furnished

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, (890 reviews)
"We were there to meet up with family members They allowed us to use the breakfast area in the evening to meet and play games."
United States
Ellen
The price is ฿3,493
฿3,957 total
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn Winchester N/Conference Center, VA
Lobby sitting area

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.0 out of 10, Very good, (1,003 reviews)
"Pet friendly. Clean well maintained rooms. After multiple stays we have NEVER seen bugs "
United States
Aaron
The price is ฿2,341
฿2,652 total
includes taxes & fees
27 May - 28 May
Motel 6 Winchester, VA
Bar (on property)

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Fun-filled family adventures await with cots, pools, and Shenandoah park just a short drive from the resort.
"Family friendly, nice pool area, gym was top notch with a lot of equipment."
United States
Joshua
The price is ฿4,248
฿4,686 total
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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
Country Inn & Suites by Radisson, Winchester, VA

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, (1004)
The price is ฿3,056
฿3,325 total
includes taxes & fees
9 Jun - 10 Jun
Country Inn & Suites by Radisson, Winchester, VA
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Family-friendly hotels with pools in Winchester

Room, 1 King Bed, Accessible, Non Smoking | Premium bedding, pillow-top beds, in-room safe, individually furnished
Hampton Inn Winchester N/Conference Center, VA

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, (890)
The price is ฿3,493
฿3,957 total
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn Winchester N/Conference Center, 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.
View all properties

Top Winchester Hotel Reviews

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

10/10 Excellent
"This was the second time I stayed here. Reasonably priced and clean. I feel safe there. Parking is right in front of the entrance. Yes, it’s right off the highway and can be slightly noisy, but that doesn’t bother me. "
Leah 3-night trip
Posted 3 hours ago
Hampton Inn Winchester N/Conference Center, VA

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 Country Inn & Suites by Radisson, Winchester, VA.
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 Bright Box Theater, Apple Blossom Mall and Winchester Little Theater. Make sure that you have lots of time for activities such as Handley Regional Library and Apple Valley Square Shopping Center.