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Check availability on Winchester Family-Friendly Hotels

Tonight
8 May - 9 May
Tomorrow
9 May - 10 May
This weekend
8 May - 10 May
Next weekend
15 May - 17 May

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, (1,002 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 ₹9,033
₹9,828 total
includes taxes & fees
1 Jun - 2 Jun
Country Inn & Suites by Radisson, Winchester, VA
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, (1,004 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 ₹6,880
₹7,658 total
includes taxes & fees
10 May - 11 May
Super 8 by Wyndham Front Royal Near Shenandoah National Park
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)
"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 ₹10,124
₹11,471 total
includes taxes & fees
24 May - 25 May
Hampton Inn Winchester N/Conference Center, 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
9.2 out of 10, Wonderful, (1,006 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 ₹8,677
₹9,441 total
includes taxes & fees
10 May - 11 May
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, (1,453 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 ₹8,972
₹9,762 total
includes taxes & fees
10 May - 11 May
Microtel Inn & Suites by Wyndham Winchester
Lobby sitting area

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.0 out of 10, Very good, (1,004 reviews)
"Pet friendly. Clean well maintained rooms. After multiple stays we have NEVER seen bugs "
United States
Aaron
The price is ₹6,408
₹7,260 total
includes taxes & fees
10 May - 11 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, (1,011 reviews)
  • cleanliness
    Child-friendly indoor pool and activities make this hotel a perfect Winchester family retreat with premium entertainment extras.
"Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service."
United States
Tong
The price is ₹9,048
₹10,127 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, (429 reviews)
  • cleanliness
    Family-friendly getaway near historic sites offers concerts, cosy rooms, and free wifi.
"We plan to stay there any time we are in the Shenandoah Valley and will recommend it to friends and family who like to travel historic byways."
United States
Sigrid
The price is ₹11,451
₹13,572 total
includes taxes & fees
10 May - 11 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, (1,005 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 ₹11,937
₹13,166 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
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, (1453)
The price is ₹8,972
₹9,762 total
includes taxes & fees
10 May - 11 May
Microtel Inn & Suites by Wyndham Winchester
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 ₹10,124
₹11,471 total
includes taxes & fees
24 May - 25 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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Air conditioning and heat worked properly, and easy to use. I like that the door to room has an alarm if door is left open. I love the big parking lot and design. Great for semi's, RV's, etc. Staff was so friendly and helpful at daytime front desk. I love the pull-down shades verses curtains. It made the room so dark. I had a good quiet night sleep. This place is safe and in a good location. Its about 2 blocks from Golden Coral. The plastic trash bags werent tied allowing more room for trash. Bigger trash cans and blue recycling basket. Check-in quick. Great price! Bed was comfy. "
Deborah 1-night trip
Posted 2 hours ago
Travelodge by Wyndham Winchester

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.