The Best Middletown, MD Chalets from $300

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Chalets in Middletown

Our top choices for Middletown chalets

"House was perfect for our needs! Clean, well equipped, nicely decorated, quiet. Hot tub was super clean and very relaxing! Close to Harper’s Ferry. Host was quick to respond and checked in on us by text. "

$376 nightly

Sep 2 - Sep 3

Total with taxes and fees

"The house was very clean upon arrival. We enjoyed spending time in the hot tub and playing pool on a kid’s pool table. It was close the Harper’s Ferry. We also saw deer very close both days we were there, and we loved this!!"

$349 nightly

Sep 18 - Sep 19

Total with taxes and fees

"We loved staying here. It’s 15 minutes from harpers ferry and very well maintained"

"Our family had a cozy weekend at the cabin. Tony was super helpful and a great host. Thank you for sharing your lovely property with us!"

$278 nightly

Sep 4 - Sep 5

Total with taxes and fees

"Adorable chalet. I’d love to come back! Clean and well stocked. "

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Top Middletown Hotel Reviews

Best Western Leesburg Hotel & Conference Center

10/10 Excellent

"Quick overnight stop on way to NC. Clean hotel with Friendly staff. We enjoyed complimentary breakfast in morning. "

Holiday Inn Express & Suites Leesburg - Historic District by IHG

10/10 Excellent

"Larry at the desk took my reservations. We booked two rooms to attend a local wedding and he was extremely helpful in securing the rooms as well as getting us in a little early. He assisted with info regarding distance to the venue and was kind and personable when we checked in. The rooms/facility were so clean and updated. Breakfast was delicious. I highly recommend this hotel."