Middletown Vacation Rentals

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Browse Select Middletown Vacation Homes

Stunning two-story building with a traditional facade, featuring a charming front porch with white railings and decorative details.

"Spectacular location. Charming and comfortable. The steps can be a challenge but are worth the effort."

Relax in this inviting outdoor seating area with sofas, armchairs, and a central table featuring a fire feature.

"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "

CA $420 total

includes taxes & fees

Aug 11 - Aug 12

Enjoy a serene view of the surrounding landscape from this room's large window.

"Location and house was just as described. Would highly recommend staying here if your looking for a location close to Harper's Ferry."

Step onto the charming porch, complete with a plush carpet and inviting bench, and enter a warm and welcoming space.

"This place was perfect for our one-night stay in Harpers Ferry. Its location is in easy walking distance of the main sites. The house is old but charming. "

CA $467 total

includes taxes & fees

Sep 2 - Sep 3

Escape to a serene lakeside haven surrounded by nature, featuring a charming gazebo and tree stumps.

"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"

"Beautiful setting with wonderful indoor and outdoor spaces. The house is charming, renovated, updated, clean, and comfortable. Great location for a family gathering to bike, visit the battlefield or visit Shepherdstown. Hosts went above and beyond to be sure we had all we needed. Would definitely stay again if in the area. "

CA $583 total

includes taxes & fees

Aug 18 - Aug 19

Enjoy cooking in this kitchen with a gas range, microwave, and toaster oven.

"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "

Modern kitchen with stove, refrigerator, and sink, featuring a central island with ample workspace.

"Our stay was great and really enjoyed the house. We had so much space to have our own time and then still be able to come together for meals and hanging in the hot tub. We now want to come back in the winter and go to the sledding hill right in front of the house! "

"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"

CA $454 total

includes taxes & fees

Aug 25 - Aug 26

Relax in a serene bedroom with a four-poster canopy bed, ornate cabinet, and potted plants.

"Great place and good location."

CA $429 total

includes taxes & fees

Aug 14 - Aug 15

Relax in a cozy forest setting with two Adirondack chairs surrounding a warm fire pit.

"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."

CA $683 total

includes taxes & fees

Aug 12 - Aug 13

Relax in this stylish living area with a large rug, two armchairs, and a sofa, surrounded by a black abstract painting and decorative panel.

"The home was exactly as expected and made for a wonderful family/friend reunion! Perfect for socializing and so close to local shops and restaurants."

CA $464 total

includes taxes & fees

Aug 19 - Aug 20

Explore historic architecture in a charming town with traditional buildings, a museum, and peaceful streets.

"Wonderful house for a great weekend away"

CA $541 total

includes taxes & fees

Sep 8 - Sep 9

Step onto the charming front porch, where a warm welcome awaits.

"Very clean, well appointed home, was a great place to stay for a few days while we explored the area. Nice outdoor space to relax and the board games and arcade game were fun for the kids. "

Stylish building with a flat roof and circular skylight, situated next to a historic brick building.

"Great location in downtown Frederick. Cozy and comfortable accommodation with great historic vibes and modern amenities. We would definitely stay here again. "

"We appreciate everything from the discrete location,hot tub and many accommodations. What a PERFECT home to stay away from home while we explored the trails and history of the surrounding area. Great eats and trails only minutes away! "

CA $602 total

includes taxes & fees

Aug 14 - Aug 15