The first Washington Monument, near Boonsboro, Maryland.

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Guest Houses in Middletown

Our top choices for Middletown guest houses

"Very clean and had everything we needed to make our own meals. Also centrally located to National parks, hiking trails (AT), and a beach."

$140 nightly

Sep 9 - Sep 10

Total with taxes and fees

"We stayed one night here on our way home and it was excellent. Plenty of space in the cabin and lots of room for our dog to stretch his legs outside. Everything was very comfortable, communication was great, and we loved the area. We hope to come back someday!"

$256 nightly

Sep 3 - Sep 4

Total with taxes and fees

"We enjoyed our stay. We liked the room and the fact it was close to town which made going places easy. "

$156 nightly

Aug 28 - Aug 29

Total with taxes and fees

"We came to get away from the city for a few days. This was the perfect location to relax with river views but close enough to walk to downtown for food. The Host was very friendly and we loved the room. "

$326 nightly

Sep 2 - Sep 3

Total with taxes and fees

"Great location! Close to walk to restaurants, activities"

$192 nightly

Aug 28 - Aug 29

Total with taxes and fees

"Lovely room, easy check in/out, and thoughtful amenities. Would absolutely stay again!"

$217 nightly

Aug 28 - Aug 29

Total with taxes and fees

"my best friend and I just got back from staying at this beautiful home. We stayed in the blue bird suite and it was lovely. This home is an ideal location to lower town. The only thing that could be better was the bed in our room. The mattress was too firm for our liking."

$191 nightly

Sep 7 - Sep 8

Total with taxes and fees

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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."