Photo by Samantha Keyes
Find Hotels with an Outdoor Pool in Middletown, VA
Check availability on Middletown Hotels with an Outdoor Pool
Our top choices for Middletown hotels with an outdoor pool
9.2 out of 10, Wonderful, (1002)
"Great stay"
Jaron
$76 nightly
The price is $82
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG
Holiday Inn Express Winchester South-Stephens City by IHGStephens City
8.2 out of 10, Very Good, (802)
"Nice stay and friendly people "
ALFRED
$74 nightly
The price is $81
Dec 20 - Dec 21
Total with taxes and fees
8.8 out of 10, Excellent, (478)
"Nice place to stay. Great staff and breakfast."
Stormy
$107 nightly
The price is $117
Dec 14 - Dec 15
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
Hampton Inn Winchester N/Conference Center, VAWinchester
9.2 out of 10, Wonderful, (846)
"Super friendly reception and perfectly clean room. "
Dwight
$103 nightly
The price is $117
Dec 19 - Dec 20
Total with taxes and fees
Baymont by Wyndham Front Royal Near Shenandoah National Park
Baymont by Wyndham Front Royal Near Shenandoah National ParkFront Royal
6.4 out of 10, (916)
"Staff was very kind! Had a nice time!"
Rio Ashley
$55 nightly
The price is $61
Dec 23 - Dec 24
Total with taxes and fees
8.2 out of 10, Very Good, (540)
"Great pool and quiet area to stay in"
Matthew
$62 nightly
The price is $69
Dec 14 - Dec 15
Total with taxes and fees
9.6 out of 10, Exceptional, (174)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
DONNA
$275 nightly
The price is $304
Dec 22 - Dec 23
Total with taxes and fees
9.8 out of 10, Exceptional, (94)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
KYLE
$309 nightly
The price is $338
Jan 8 - Jan 9, 2026
Total with taxes and fees
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.
Top Middletown Hotel Reviews
Holiday Inn Winchester Se-Historic Gateway by IHG
10/10 Excellent
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