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Check availability on Winchester Family-Friendly Hotels

Our top choices for Winchester family-friendly hotels

Exterior

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, (1,000 reviews)
  • cleanliness
    Family-friendly fun at this Winchester inn begins with an indoor pool, complimentary breakfast, and premium entertainment options.
The price is Rp1.644.841
Rp1.789.588 total
includes taxes & fees
9 Jun - 10 Jun
Country Inn & Suites by Radisson, Winchester, VA
Exterior

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, (888 reviews)
The price is Rp1.877.272
Rp2.126.949 total
includes taxes & fees
25 May - 26 May
Hampton Inn Winchester N/Conference Center, VA
Lobby

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,457 reviews)
  • cleanliness
    A kid-friendly getaway with indoor pool and free breakfast, just minutes from the Shenandoah Valley Discovery Museum.
The price is Rp1.693.424
Rp1.842.445 total
includes taxes & fees
18 May - 19 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
9.2 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 Rp1.550.820
Rp1.687.293 total
includes taxes & fees
31 May - 1 Jun
Quality Inn Winchester
Lobby sitting area

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.0 out of 10, Very good, (1,000 reviews)
The price is Rp1.188.193
Rp1.346.222 total
includes taxes & fees
17 May - 18 May
Motel 6 Winchester, VA
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, (1,000 reviews)
  • cleanliness
    Child-friendly indoor pool and activities make this hotel a perfect Winchester family retreat with premium entertainment extras.
The price is Rp1.537.888
Rp1.725.580 total
includes taxes & fees
24 May - 25 May
Holiday Inn Winchester Se-Historic Gateway by IHG
Dining

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (430 reviews)
  • cleanliness
    Family-friendly getaway near historic sites offers concerts, cosy rooms, and free wifi.
The price is Rp2.123.334
Rp2.516.623 total
includes taxes & fees
17 May - 18 May
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, (1,001 reviews)
  • cleanliness
    Fun-filled family adventures await with cots, pools, and Shenandoah park just a short drive from the resort.
The price is Rp2.283.414
Rp2.518.606 total
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (1,003 reviews)
  • cleanliness
    Family-friendly hotel with spacious rooms offers premium entertainment and free perks near Shenandoah Valley Discovery Museum.
The price is Rp1.336.914
Rp1.454.562 total
includes taxes & fees
9 Jun - 10 Jun
Sleep Inn & Suites Winchester near University
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

Exterior
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, (1000)
The price is Rp1.644.841
Rp1.789.588 total
includes taxes & fees
9 Jun - 10 Jun
Country Inn & Suites by Radisson, Winchester, VA
View all properties

Family-friendly hotels with pools in Winchester

Exterior
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, (888)
The price is Rp1.877.272
Rp2.126.949 total
includes taxes & fees
25 May - 26 May
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

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

6/10 Okay
"This was the fourth time I stayed here. The place needs some serious renovations. Won't stay there again! "
Klaus 1-night trip
Posted 2 hours ago
Mimslyn Inn Historic Hotels Of America

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.