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Find Hotels with a Pool in Middletown, VA

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Check availability on Middletown Hotels with a Pool

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

Top Middletown Hotels with a Pool

Indoor pool
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (765)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is SAR 273
SAR 297 total
includes taxes & fees
7 Jan - 8 January 2026
TRU By Hilton Winchester
Indoor pool
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
Indoor pool
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
Indoor pool
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
Indoor pool
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1012)
"Great hotel!"
United States
CHARLES
The price is SAR 475
SAR 539 total
includes taxes & fees
14 Dec - 15 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Indoor pool
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
Winchester
9.2 out of 10, Wonderful, (2219)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is SAR 396
SAR 431 total
includes taxes & fees
15 Dec - 16 Dec
La Quinta Inn & Suites by Wyndham Winchester
Indoor pool
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (774)
"Clean room, courteous and professional staff. Great breakfast selections"
United States
Lauris
The price is SAR 402
SAR 437 total
includes taxes & fees
14 Dec - 15 Dec
SpringHill Suites by Marriott Winchester
Indoor pool
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
Indoor pool
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (797)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is SAR 348
SAR 378 total
includes taxes & fees
11 Dec - 12 Dec
Fairfield Inn & Suites by Marriott Winchester
Seasonal outdoor pool
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
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 20 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

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Frequently asked questions

What are some accommodations with pools in Middletown?
Econo Lodge Inn & Suites: Offers buffet, an indoor pool, and complimentary wired internet access. La Quinta Inn & Suites by Wyndham Winchester: Provides daily, an indoor pool, and free self parking. Microtel Inn & Suites by Wyndham Winchester: Offers 2 restaurants, an indoor pool, and a full-service spa. Comfort Inn & Suites Winchester: Features daily, an indoor pool, and free self parking. The George Washington Hotel, A Wyndham Grand Hotel: Provides a snack bar/deli, a pool, and daily.
What is there to see and do in Middletown?
Surround yourself with nature at Shenandoah River and Cedar Creek and Belle Grove National Historical Park. Discover sights such as Belle Grove Plantation, Wayside Theater, and Cedar Creek Battlefield Foundation during your stay. The bars, restaurants, and historic landmarks are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Middletown?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Middletown in the warmest months of July, August, or June when the average temp is 72°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 36°F.