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Find Family Hotels in Middletown, VA

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Check availability on Middletown Family Hotels

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Middletown Family Hotels

Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
The price is SAR 270
SAR 336 total
includes taxes & fees
21 Dec - 22 Dec
Wayside Inn
Breakfast area
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2.0 star property
Middletown
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
The price is SAR 233
SAR 257 total
includes taxes & fees
14 Dec - 15 Dec
Econo Lodge Inn & Suites
Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1374)
"Excellent accommodations"
United States
Loretta
The price is SAR 270
SAR 294 total
includes taxes & fees
5 Jan - 6 January 2026
Microtel Inn & Suites by Wyndham Winchester
Lobby
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, (1004)
"Have stayed here multiple times -always good"
United States
Robert
The price is SAR 320
SAR 348 total
includes taxes & fees
4 Jan - 5 January 2026
Country Inn & Suites by Radisson, 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, (1005)
"Clean room, nicely furnished."
United States
Marilyn
The price is SAR 278
SAR 313 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Lobby
Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal

2.0 star property
Front Royal
7.6 out of 10, Good, (1002)
"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
The price is SAR 221
SAR 246 total
includes taxes & fees
9 Dec - 10 Dec
Super 8 by Wyndham Front Royal
Lobby
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 star property
Winchester
7.8 out of 10, Good, (1000)
"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
The price is SAR 256
SAR 279 total
includes taxes & fees
4 Jan - 5 January 2026
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

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 SAR 366
SAR 415 total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Lobby
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1006)
"Great stay"
United States
Jaron
The price is SAR 284
SAR 309 total
includes taxes & fees
15 Dec - 16 Dec
Quality Inn Winchester
Porch
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 star property
Winchester
9.0 out of 10, Wonderful, (1002)
"Staff, clean room, very comfortable bed!"
United States
Terri
The price is SAR 372
SAR 422 total
includes taxes & fees
4 Jan - 5 January 2026
Hampton Inn Winchester-University/Mall Area
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Great hotel!"
CHARLES 1-night trip
Posted 11 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

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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.