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Compare 524 Vacation Homes in Chestertown with updated reviews, rates, and availability.

"Perfect Location - Easy Process - Comfortable Home!"

"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "

"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"

"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "

AED 1,015 total

includes taxes & fees

1 Apr - 2 Apr

"Great wx and weekend visit to the Naval Academy. Walking distance to everything and neighborhood was a nice getaway from main street "

"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."

"Typical row house with lots of stairs but very clean & comfortable. Loved having a pack & play for our 2 year old granddaughter. Host was very nice. Would stay again."

"A great location and plenty of room for visiting groups to be in and out. Clean and well provisioned. Parking was a great feature as well."

"Wonderful stay. The home had everything we needed and was very comfortable. Can't beat the location and with 2.5 nice bathrooms and 4 beds everyone was comfortable. Wonderful to have the washer and dryer. Host was very easy to communicate with. It is an old historic house so the stairway is steep if anyone in your party has mobility issues. "

House, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

"Clean, Spacious, and exactly as advertised! "

AED 901 total

includes taxes & fees

27 Mar - 28 Mar

"Can’t wait to come back during warmer weather. It was a perfect over night stay. "

AED 2,398 total

includes taxes & fees

7 Apr - 8 Apr

"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. "

"Gorgeous views and surroundings"

"The house was very clean and super comfortable. We didn’t cook anything during our stay but the kitchen looked well stocked. Beds were comfortable. The location was awesome. Very short walk to downtown and just steps to the Naval Academy visitors entrance. We very much enjoyed our stayed!"

"I visited my midshipman and I couldn’t have asked for a better place! Very comfortable & spacious-yet not too big. It was as if we were home. Location was awesome. Mike was great with immediate communication-especially in preparing us with info well before our check in day! I would definitely stay here again! "

"I booked this house for a week as a quiet fishing trip get away. For starters Leone is awesome, always responds quick and is an amazing host.The house itself: was very clean, cozy, and had everything needed for a very comfortable stay. Other reviews said furniture was uncomfortable but I thought it was fine. Location was 3 min to foodlion, 10ish min to gas station, and about 16 min to large store for fishing gear. TV has netflix and lots of other shows to watch if thats what you want but most of...

"Loved staying at Chesapeake Cottage! Perfect location on the east bay but just minutes from the Chesapeake Bay. The view were spectacular especially at at night since we were there during the Blood Moon. The house is beautifully decorated with a wonderful sun room overlooking the water. The house is well equipped and comfortable. I look forward to going back during warmer weather, but even in March, the visit was agreat, especially with the fire pit out back. "

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Other property types in Chestertown

"Perfect Location - Easy Process - Comfortable Home!"

"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "