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Our top choices for Winchester family-friendly hotels

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,449 reviews)
  • cleanliness
    A kid-friendly getaway with indoor pool and free breakfast, just minutes from the Shenandoah Valley Discovery Museum.
The price is S$124
includes taxes & fees
23 Apr - 24 Apr
Microtel Inn & Suites by Wyndham Winchester

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, (878 reviews)
The price is S$154
includes taxes & fees
29 Apr - 30 Apr
Hampton Inn Winchester N/Conference Center, VA

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, (1,001 reviews)
The price is S$89
includes taxes & fees
19 Apr - 20 Apr
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodation.
The price is S$116
includes taxes & fees
30 Apr - 1 May
Quality Inn Winchester

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 S$130
includes taxes & fees
18 May - 19 May
Country Inn & Suites by Radisson, Winchester, VA

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, (1,001 reviews)
  • cleanliness
    Child-friendly indoor pool and activities make this hotel a perfect Winchester family retreat with premium entertainment extras.
The price is S$142
includes taxes & fees
26 Apr - 27 Apr
Holiday Inn Winchester Se-Historic Gateway by IHG

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.0 out of 10, Very good, (1,001 reviews)
The price is S$98
includes taxes & fees
20 Apr - 21 Apr
Motel 6 Winchester, VA

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, (1,001 reviews)
  • cleanliness
    Fun-filled family adventures await with cots, pools, and Shenandoah park just a short drive from the resort.
The price is S$153
includes taxes & fees
26 Apr - 27 Apr
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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, (828 reviews)
The price is S$169
includes taxes & fees
3 May - 4 May
Holiday Inn Express Hotel & Suites Winchester by IHG

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (426 reviews)
  • cleanliness
    Family-friendly getaway near historic sites offers concerts, cosy rooms, and free wifi.
The price is S$183
includes taxes & fees
19 Apr - 20 Apr
Wayside Inn
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.

Choose what matters most at family-friendly hotels in Winchester

Family-friendly hotels with free breakfast in Winchester

Family-friendly hotels with pools in 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.

Top Winchester Hotel Reviews

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 Handley Regional Library. Make sure that you have lots of time for activities such as Winchester Little Theater and Apple Valley Square Shopping Center.

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