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Kid Friendly Hotels in Middletown

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Check availability on Middletown Family friendly Hotels

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Middletown family-friendly hotels

Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (418)
"Historic inn. "
United States
David
The price is RM291
RM362 total
includes taxes & fees
28 Dec - 29 Dec
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
The price is RM279
RM308 total
includes taxes & fees
28 Dec - 29 Dec
Econo Lodge Inn & Suites Middletown - Winchester South
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, (1001)
"Good condition "
United States
Phillip
The price is RM251
RM279 total
includes taxes & fees
7 Jan - 8 Jan 2026
Super 8 by Wyndham Front Royal
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, (1404)
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is RM320
RM349 total
includes taxes & fees
5 Jan - 6 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
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, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is RM333
RM363 total
includes taxes & fees
25 Jan - 26 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Lobby
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
The price is RM306
RM333 total
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn Winchester
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, (1000)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is RM316
RM355 total
includes taxes & fees
24 Jan - 25 Jan 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
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, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is RM395
RM436 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Lobby
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, (1000)
"great stay with breakfast too"
United States
James
The price is RM247
RM269 total
includes taxes & fees
25 Jan - 26 Jan 2026
Sleep Inn & Suites Winchester near University
Premium bedding, desk, soundproofing, iron/ironing board
Econo Lodge Woodstock - Shenandoah Valley I-81

Econo Lodge Woodstock - Shenandoah Valley I-81

Econo Lodge Woodstock - Shenandoah Valley I-81
2.0 star property
Woodstock
7.2 out of 10, Good, (637)
"We really appreciated the restraunt on site, the food was great, ate there twice. The hotel was in a great location, the room was small and the bathroom had no counter space but all in all it was a nice stay and could stay here again."
United States
Zelda
The price is RM206
RM232 total
includes taxes & fees
27 Jan - 28 Jan 2026
Econo Lodge Woodstock - Shenandoah Valley I-81
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 Middletown Hotel Reviews

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

10/10 Excellent
"Very nice stay"
SOPHIE 1-night trip
Posted 5 days ago
Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Frequently asked questions

What's Middletown like for family-friendly holidays?
You may want to consider the historic destination of Middletown if you've been thinking about a trip for the whole family. The entertainment, hockey matches and theatres 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 centre.
What's the best family accommodation in Middletown?
Econo Lodge Inn & Suites Middletown - Winchester South 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 holiday in Middletown?
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 Middletown is 1088 mm.
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 that you and your family will enjoy exploring while you are staying in Middletown. Make sure that you have lots of time for activities such as Virginia River Trips and Front Royal Entrance Shenandoah National Park.

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