Middletown Cottages

A stone tower with a staircase leading up to it.

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Our top choices for Middletown cottages

1. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Frederick

Andrew F.

includes taxes & fees

22 Sept - 23 Sept

2. Quaint Mini Cottage in Shepherdstown - Walking Distance

Shepherdstown

John

includes taxes & fees

13 Sept - 14 Sept

3. The Carriage House at Carrot Top Cottage

Harpers Ferry

Michael

includes taxes & fees

15 Sept - 16 Sept

4. Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

Boonsboro

includes taxes & fees

13 Sept - 14 Sept

5. Rural & Historic Detour Escape w/ Horses On-site!

Keymar

includes taxes & fees

20 Sept - 21 Sept

6. Woodsy Retreat with a Hot Tub and Seasonal Views!

Harpers Ferry

Amy P.

includes taxes & fees

24 Sept - 25 Sept

7. Cottage w/ Hot Tub and 100-Mile Valley Views!

Harpers Ferry

Anonymous traveller

includes taxes & fees

21 Sept - 22 Sept

8. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Harpers Ferry

Zachary S.

includes taxes & fees

13 Sept - 14 Sept

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Top Middletown Hotel Reviews

Best Western Historic Frederick

8/10 Good

"Bathroom was small, there’s nothing in the shower to hold things like soap or shampoo, there needs to better lighting in the center of the room. The room was clean and the bed was comfortable."

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent

"I chose this hotel because we wanted a room with 3 beds. There weren't a lot of good choices at this location. I was a little concerned because the photos on the website made the furnishings look kind of old and shabby compared to others. As it turned out, the room and furnishings were very nice and modern. Time to update the website!"

Comfort Inn Frederick - Ballenger Creek

10/10 Excellent

"Check-in was support easy and all the staff was friendly. One of our cards wasn't working and one of the maintenance men helped us get back in our room. The room was clean and the surrounding area had lots of shops and restaurants. The hotel also had ample parking."

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