Search Family-Friendly Hotels in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Winchester Family-Friendly Hotels

Top Winchester Family-Friendly Hotels

Country Inn & Suites by Radisson, Winchester, VA
Lobby

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1002)
"Stay was pleasant. A nice pet friendly option "
Vicki
The price is ฿3,146
฿3,423 total
includes taxes & fees
20 Jul - 21 Jul
Country Inn & Suites by Radisson, Winchester, VA
Fairfield Inn & Suites Strasburg Shenandoah Valley
Exterior

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 star property
9.0 out of 10, Wonderful, (1000)
"A very nice and friendly hotel"
Eileen
The price is ฿3,284
฿3,655 total
includes taxes & fees
17 Aug - 18 Aug
Fairfield Inn & Suites Strasburg Shenandoah Valley
Quality Inn
Exterior

Quality Inn

2.5 star property
9.2 out of 10, Wonderful, (1000)
"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. "
Margaret
The price is ฿3,008
฿3,273 total
includes taxes & fees
24 Jul - 25 Jul
Quality Inn
Hampton Inn Front Royal
Exterior

Hampton Inn Front Royal

2.5 star property
9.0 out of 10, Wonderful, (1008)
"Very dog friendly ! Clean "
Shannon
The price is ฿3,560
฿3,962 total
includes taxes & fees
17 Aug - 18 Aug
Hampton Inn Front Royal
Red Roof Inn Winchester, VA
Desk, blackout curtains, free cots/infant beds, free WiFi

Red Roof Inn Winchester, VA

2.0 star property
7.4 out of 10, Good, (1001)
"Nice and close to sightseeing places."
Terry
The price is ฿2,272
฿2,472 total
includes taxes & fees
20 Jul - 21 Jul
Red Roof Inn Winchester, VA
Spark by Hilton Winchester
Lobby

Spark by Hilton Winchester

3.0 star property
9.0 out of 10, Wonderful, (1002)
"A great hotel for our
family stay
. We really enjoyed the pool. The only down side was that the breakfast only had a few choices, but everyone in the
family
at least found one thing they liked. We could stay here again. The downsides with the hotel was that the room lacked shampo and shower gel, we had to ask in the reception for that. And that the breakfast was served on plastic one time use things, it’s not sustainable to keep doing that for a big chain like Hilton. "
Linda
The price is ฿2,953
฿3,346 total
includes taxes & fees
17 Aug - 18 Aug
Spark by Hilton Winchester
The George Washington Hotel, A Wyndham Grand Hotel
2 restaurants, breakfast, lunch, dinner served; American cuisine

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1004)
"Our stay was wonderful. The rooms were clean, all staff was helpful, pool/hot tub was perfect with the cold weather and the entertainment at the bar was phenomenal. "
Amanda
The price is ฿4,112
฿4,659 total
includes taxes & fees
24 Jul - 25 Jul
The George Washington Hotel, A Wyndham Grand Hotel
Holiday Inn Express Winchester South-Stephens City by IHG
Exterior

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very good, (757)
"This hotel was very safe, clean and
family friendly
. "
Jennifer
The price is ฿2,580
฿2,807 total
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express Winchester South-Stephens City by IHG
Quality Inn Stephens City - Winchester South
Free daily continental breakfast

Quality Inn Stephens City - Winchester South

2.5 star property
8.0 out of 10, Very good, (589)
"Super friendly and quiet. Even though pet friendly. Got my dog fix in. Super comfortable bed and pillows. "
Susan
The price is ฿2,629
฿2,861 total
includes taxes & fees
30 Jul - 31 Jul
Quality Inn Stephens City - Winchester South
Hotel Strasburg
Building design

Hotel Strasburg

3.0 star property
7.8 out of 10, Good, (731)
"The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!"
Merry
Hotel Strasburg
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.

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