Find Family Hotels in Winchester, VA from CA $99

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Winchester Family Hotels

Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.4 out of 10, Exceptional, (1004)
"Beautiful town. The hotel is beautiful. "
The price is CA $171
CA $194 total
includes taxes & fees
Jun 16 - Jun 17
The George Washington Hotel, A Wyndham Grand Hotel
Indoor pool
Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
9.0 out of 10, Wonderful, (1000)
"Very friendly staff and free breakfast"
The price is CA $168
CA $187 total
includes taxes & fees
Jun 6 - Jun 7
Fairfield Inn & Suites Strasburg Shenandoah Valley
Lobby
Spark by Hilton Winchester
3.0 star property
9.0 out of 10, Wonderful, (1004)
"The rooms were large and very clean and comfortable!"
The price is CA $120
CA $136 total
includes taxes & fees
Jun 24 - Jun 25
Spark by Hilton Winchester
Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1345)
"We enjoyed our stay at la quinta. It is clean and pet friendly."
The price is CA $145
CA $158 total
includes taxes & fees
May 26 - May 27
La Quinta Inn & Suites by Wyndham Winchester
Exterior
Quality Inn
2.5 star property
8.8 out of 10, Excellent, (999)
"Room was clean and comfortable, staff was very nice, breakfast was good as well. We will definitely stay here again. "
The price is CA $127
CA $138 total
includes taxes & fees
Jun 9 - Jun 10
Quality Inn
Exterior
Hampton Inn Front Royal
2.5 star property
8.8 out of 10, Excellent, (1002)
"Gym was nice but floor was under renovation "
The price is CA $168
CA $186 total
includes taxes & fees
Jun 2 - Jun 3
Hampton Inn Front Royal
Exterior
Fairfield Inn & Suites by Marriott Winchester
2.5 star property
8.8 out of 10, Excellent, (592)
"Close to highway, easy to find"
The price is CA $138
CA $151 total
includes taxes & fees
May 26 - May 27
Fairfield Inn & Suites by Marriott Winchester
Desk, laptop workspace, blackout drapes, iron/ironing board
Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
8.6 out of 10, Excellent, (1001)
"Great Hotel"
The price is CA $134
CA $146 total
includes taxes & fees
May 26 - May 27
Country Inn & Suites by Radisson, Winchester, VA
Exterior
Holiday Inn Express Winchester South-Stephens City, an IHG Hotel
2.5 star property
8.2 out of 10, Very good, (676)
"Very clean"
The price is CA $159
CA $173 total
includes taxes & fees
Jun 9 - Jun 10
Holiday Inn Express Winchester South-Stephens City, an IHG Hotel
Desk, soundproofing, iron/ironing board, cribs/infant beds
Twi-Lite Inn
2.0 star property
8.2 out of 10, Very good, (453)
"Staying at the Twi-Lite was like being in a time capsule in the best way. Our room was super clean, the beds were great, and we appreciated the convenience of the microwave and refrigerator in our room. Loved the retro feel of this mid century property. The pool looked pristine, although the weather was not quite warm enough for us to be tempted to use it. If we are ever back in Front Royal we would stay here again. "
The price is CA $113
CA $125 total
includes taxes & fees
May 29 - May 30
Twi-Lite Inn
Don't see what you're looking for?
See all available properties 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.

Popular hotels great for families

Most favorite kid-friendly stays in Winchester in 2024
Hotels with pools in Winchester

Hotels with pools

Hotels with pools
Hotels with kitchenette in Winchester

Hotels with kitchenette

Hotels with kitchenette

Winchester Family Hotels information

 

Family Hotels in Winchester

36

Highest price
CA $171
Cheapest price
CA $99
Number of guest reviews
8,901
Total number of hotels in Winchester
1,861

 

Frequently asked questions

What's Winchester like for family-friendly vacations?
The historic destination of Winchester is a good choice if you’ve been thinking about a trip with your kids. The entertainment, soaring skyscrapers, and theaters are just a few things that make this an attractive family vacation spot. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city center.
What's the best hotel for a family vacation to Winchester?
Country Inn & Suites by Radisson, Winchester, VA is a hotel with an indoor pool and free parking, and it’s a top choice on Expedia for families. Other good choices for your stay with the kids include Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel and Sleep Inn & Suites.
How many family-friendly hotels should I expect to find in Winchester?
Expedia has 9 family-friendly hotels and other accommodations in Winchester.
When's the best time to book a family-friendly vacation in Winchester?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you and the family might want to check out some interesting spots such as Apple Blossom Mall, Bright Box Theater, and Winchester Little Theater. Make sure you have lots of time for activities like Handley Regional Library and Nalls Farm Market.

Recent Reviews in Winchester
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

5/5 Excellent
Stay in winchester virginia
"We enjoyed our stay at la quinta. It is clean and pet friendly."
A verified traveller stayed at La Quinta Inn & Suites by Wyndham Winchester
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester