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Check availability on Winchester Family-Friendly Hotels

Next weekend
12 Jun - 14 Jun
In two weeks
19 Jun - 21 Jun

Our top choices for Winchester family-friendly hotels

Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar) | 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, (897 reviews)
The price is ฿3,523
฿3,992 total
includes taxes & fees
21 Jun - 22 Jun
Hampton Inn Winchester N/Conference Center, VA
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, (1,003 reviews)
  • cleanliness
    Family-friendly fun at this Winchester inn begins with an indoor pool, complimentary breakfast, and premium entertainment options.
The price is ฿3,070
฿3,340 total
includes taxes & fees
28 Jun - 29 Jun
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, (1,001 reviews)
  • cleanliness
    Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodation.
The price is ฿2,891
฿3,145 total
includes taxes & fees
21 Jun - 22 Jun
Quality Inn Winchester
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.
The price is ฿3,043
฿3,311 total
includes taxes & fees
21 Jun - 22 Jun
Microtel Inn & Suites by Wyndham Winchester
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, (1,006 reviews)
The price is ฿2,394
฿2,665 total
includes taxes & fees
8 Jun - 9 Jun
Super 8 by Wyndham Front Royal Near Shenandoah National Park
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, (1,002 reviews)
  • cleanliness
    Child-friendly indoor pool and activities make this hotel a perfect Winchester family retreat with premium entertainment extras.
The price is ฿3,312
฿3,702 total
includes taxes & fees
14 Jun - 15 Jun
Holiday Inn Winchester Se-Historic Gateway by IHG
Dining

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (436 reviews)
  • cleanliness
    Family-friendly getaway near historic sites offers concerts, cosy rooms, and free wifi.
The price is ฿3,985
฿4,723 total
includes taxes & fees
15 Jun - 16 Jun
Wayside Inn
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.
The price is ฿4,194
฿4,626 total
includes taxes & fees
14 Jun - 15 Jun
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Lobby

Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
2.0 star property
Front Royal
7.0 out of 10, Good, (517 reviews)
The price is ฿2,131
฿2,372 total
includes taxes & fees
9 Jun - 10 Jun
Motel 6 Front Royal, VA
Free daily on-the-go breakfast

Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
2.0 star property
Winchester
6.6 out of 10, (526 reviews)
  • cleanliness
    Friendly Winchester escape where kids enjoy complimentary breakfast and convenient amenities near family attractions.
The price is ฿2,420
฿2,633 total
includes taxes & fees
8 Jun - 9 Jun
Days Inn 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.
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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

Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar) | 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, (897)
The price is ฿3,523
฿3,992 total
includes taxes & fees
21 Jun - 22 Jun
Hampton Inn Winchester N/Conference Center, VA
View all properties

Family-friendly hotels with pools in Winchester

Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar) | 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, (897)
The price is ฿3,523
฿3,992 total
includes taxes & fees
21 Jun - 22 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

Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"We just overnighted but it would be delightful to stay much longer and take advantage of the spa, local wineries, golf, etc. The rooms and facilities are beautiful."
Molly L 1-night trip
Posted less than an hour ago
Lansdowne Resort and Spa

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?
Microtel Inn & Suites by Wyndham Winchester is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Other good options for your stay with the children include Holiday Inn Winchester Se-Historic Gateway by IHG 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 Bright Box Theater, Apple Blossom Mall and Handley Regional Library. Make sure that you have lots of time for activities such as Winchester Little Theater and Apple Valley Square Shopping Center.