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Compare 518 Vacation Homes in Eastern Shore with updated reviews, rates, and availability.

"Excellent.communication with property manager. The house was beautiful with plenty of space for our group of 8."

"Beautiful location and amazing views!"

"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "

"Me and my three friends really enjoyed our stay at this spacious and beautiful townhouse. Check in/out was easy. It was very much the off season and we enjoyed the beautiful and peaceful neighborhood. "

"Perfect spot near all the major bars and beautiful hom."

AED 1,133 total

includes taxes & fees

2 Feb - 3 Feb

"My group enjoyed our stay at this property. Excellent location near boardwalk. Next to convenient deli. Host messaged us in advance to let us know that the home comes with a small starter supply of toilet paper/paper towels, so renters should consider bringing additional supply for convenience depending on size of group/length of stay."

Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."

Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"

"Great location with gorgeous views. Top-notch amenities. Loads of space for multiple families. Thank you!"

"We enjoyed our stay in this condo with everything. Conveniently located, we loved the ocean views near the boardwalk. Restaurants and shops located nearby were a plus. The kitchen was well equipped and the bathrooms were spacious, not cramped. We would definitely stay here again!"

"Three days of golf and two evenings to enjoy OCMD. My only negative is receiving the entry code. I understand the need to safeguard the property, but I had 11 guest that I wanted to know where the condo was and how to enter. No big deal it all worked out well."

"We stayed at this location to celebrate a winter birthday with our family and a few friends! The house was clean, well maintained and the location was perfect. Having two bedrooms with attached bathrooms is great for multiple couples staying together under one roof. Overall, we only have positive things to say about our stay. "

AED 1,137 total

includes taxes & fees

9 Feb - 10 Feb

"Loved staying here! Pay attention to the description by the owner! The house takes you back in time a little bit, but it’s so nice! Great location, nice neighborhood. The main living area is larger in person than what it looks like in the photos. We have already booked our next stay here!"

"Overall, it's a nice apartment. Needs a deep cleaning. Get rid of the rugs all together. Would stay again."

"Our second stay was as awesome as the first. Great location, awesome host ...we can't wait for next year 😁"

"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"

"Nice location down town. House was just as the pictures showed. "

"This charming home was perfect for our retreat needs! It was well kept, clean and spacious. The parking spaces are located directly under the unit, which resembles a carport, and are very convenient for unloading and loading your vehicles. The multi-level decks give you beautiful views of the ocean and the bay and are a perfect spot to relax after a day at the beach. We hope to stay here again next year! 10 out of 10 recommend!"

"Great location close to boardwalk and beach. The property was old but everything was clean and in working condition. I would have given 5 stars but some beds were uncomfortable. "