A stone tower with a staircase leading up to it.

Find Hotels with a Pool in Middletown, MD

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Check availability on Middletown Hotels with a Pool

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Our top choices for Middletown hotels with a pool

A two-story house with a front porch, a chimney, and a small garden with pumpkins.

1. Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (162 reviews)
"Great little spot!"
United States
Shelby W.
The price is ￥13,471
￥39,142 total
includes taxes & fees
Nov 9 - Nov 10
Charming "Cream of the Crop" Cape ~❤️of Middletown
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

2. Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (118 reviews)
"Beautiful property! Owner is very quick to communicate and did a fantastic job making it a very relaxing place to stay!"
United States
Cindy B.
The price is ￥15,848
￥36,454 total
includes taxes & fees
Nov 15 - Nov 16
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A log cabin interior with a wooden bench, a leather sofa, a coffee table, and a bookshelf.

3. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
The price is ￥30,111
￥34,605 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Downtown Cabin - Family Friendly
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

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent
"Staff was nice and great to interact with while I was there"
Gregory Alan 2-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Hagerstown, MD

Frequently asked questions

What are some accommodations with pools in Middletown?
Quality Inn Harpers Ferry - Charles Town: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Best Western Historic Frederick: Provides buffet, an indoor pool, and LCD televisions. Fairfield Inn & Suites by Marriott Hagerstown: Offers buffet, an indoor pool, and complimentary wired internet access. Country Inn & Suites by Radisson, Frederick, MD: Provides buffet, an indoor pool, and free self parking. Comfort Inn Frederick - Ballenger Creek: Features a snack bar/deli, an indoor pool, and buffet.
What is there to see and do in Middletown?
Make a point to visit attractions like Baker Park and Frederick Fairgrounds. Discover sights such as South Mountain State Park, Maryland National Golf Club, and Gambrill State Park during your stay.
When is the best time to book a hotel with a pool in Middletown?
You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Middletown in the hottest months of July, August, or June when the average temperature is 72°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temperature is 36°F.