A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

Find Hotels with a Pool in Middletown, VA from CA $94

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Check availability on Middletown Hotels with a Pool

This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for Middletown hotels with a pool

A cozy living room with a fireplace, patterned chairs, and a dining area with wooden furniture.

1. Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (464 reviews)
"We enjoyed our short stay at Wayside. We were greeted by Amanda with a very warm and friendly welcome. She kindly let us check in early and gave us a few ideas to explore."
United States
Gerry
The price is CA $90
CA $113 total
includes taxes & fees
Dec 8 - Dec 9
Wayside Inn
A dining area with a high ceiling, wooden beams, and a chandelier. There is a painting on the wall and an American flag. Tables and chairs are arranged for dining.

2. Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (333 reviews)
"Place is in poor repair."
United States
Craig
The price is CA $88
CA $97 total
includes taxes & fees
Nov 29 - Nov 30
Econo Lodge Inn & Suites Middletown - Winchester South
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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Choose what matters most at hotels with a pool in Middletown

Breakfast included
4 stars

Top Middletown Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Excellent Hotel . Comfortable Rooms and Beds, Great Location"
Christopher 3-night trip
Posted 3 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Frequently asked questions

What are some accommodations with pools in Middletown?
Wayside Inn: Offers 2 restaurants, an indoor pool, and a full-service spa. The George Washington Hotel, A Wyndham Grand Hotel: Features a health club, an indoor pool, and daily. Travelodge by Wyndham Winchester: Offers buffet, an indoor pool, and complimentary wired internet access. TRU By Hilton Winchester: Features daily, a seasonal outdoor pool, and complimentary wired internet access. La Quinta Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool, and free self parking.
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 and Jackson's Chase Golf Course 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.

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