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Find kid-friendly hotels & resorts in Middletown, VA from $66

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Check availability on Middletown Family Hotels

Our top choices for Middletown family-friendly hotels

Dining
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
$89 nightly
The price is $98
Dec 14 - Dec 15
Total with taxes and fees
Wayside Inn
Breakfast area
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
$62 nightly
The price is $68
Dec 18 - Dec 19
Total with taxes and fees
Econo Lodge Inn & Suites Middletown - Winchester South
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, (1375)
"Excellent accommodations"
United States
Loretta
$72 nightly
The price is $78
Jan 11 - Jan 12, 2026
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester
Lobby
Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal
2.0 star property
Front Royal
7.6 out of 10, Good, (1003)
"The staff was friendly and attentive. The room was clean. The breakfast was good, with pancakes, toast, cereal, juice, and coffee. Good location for visiting Shenandoah National Park."
United States
Teresa
$59 nightly
The price is $66
Dec 12 - Dec 13
Total with taxes and fees
Super 8 by Wyndham Front Royal
Lobby
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, (1001)
"Have stayed here multiple times -always good"
United States
Robert
$84 nightly
The price is $92
Jan 11 - Jan 12, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

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, (1002)
"Clean room, quiet area, good breakfast"
United States
Laurie
$73 nightly
The price is $79
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
Standard Double Room, 2 Double Beds, Non Smoking | Blackout drapes, iron/ironing board, free cribs/infant beds
Quality Inn Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1001)
"Great stay"
United States
Jaron
$76 nightly
The price is $82
Dec 17 - Dec 18
Total with taxes and fees
Quality Inn Winchester
Lobby sitting area
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1001)
"The rooms were clean and the facility seemed safe and well maintained. The room had seen many patches and repairs and had a distinct smell. The indoor pool, “gym” and breakfast were a plus. "
United States
tyshia
$68 nightly
The price is $74
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sleep Inn & Suites Winchester near University
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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, (1001)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
$101 nightly
The price is $111
Dec 17 - Dec 18
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Restaurant
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, (846)
"Super friendly reception and perfectly clean room. "
United States
Dwight
$103 nightly
The price is $117
Dec 17 - Dec 18
Total with taxes and fees
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.
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Top Middletown Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Comfortable and clean room."
Linda 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

What's Middletown like for family-friendly vacations?
You might want to consider the historic destination of Middletown if you've been thinking about a trip for the whole family. The entertainment, hockey games, and theaters are just a few things that make this an attractive place for families. Take to the air and fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 30.4 mi (48.9 km) from the city center.
What's the best place to stay for families in Middletown?
Econo Lodge Inn & Suites is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in Middletown?
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 Middletown is 43 inches.
What's there to see and do with your family in Middletown?
Wayside Theater, Dinosaur Land, and Front Royal Visitor's Center are interesting attractions you and your family will enjoy exploring while you are staying in Middletown. Make sure you have lots of time for activities like Front Royal Entrance Shenandoah National Park and Apple Blossom Mall.

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