Somewhere over the rainbow... Terrific view on the plane back to the North.

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Vacation Homes in Chestertown

Our top choices for Chestertown vacation homes

"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "

"Loved the location and the pristine condition of the house. "

"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."

"We stayed here for about a month while we found and bought a house. It was very comfortable, near shopping, near a dog park, and a great place to relax after work as well as make our meals and do laundry. Owners were quick to respond to questions or issues, friendly and easy to get along with."

AED 1,386 total

includes taxes & fees

28 Aug - 29 Aug

"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "

"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "

"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "

"It was great!"

"Great location for our team to stay during Annapolis sail show. "

"The host was amazing. The property was as described and was perfect for our group. "

"Excellent property, great communication with the hosts. Quite and relaxing"

Fridge, microwave, dishwasher, coffee/tea maker

"Nice place with everything I could want. Would stay there again!"

"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "

"Great location"

"The property is everything it claims to be & more. Awesome location on the bay. Great accommodations. So peaceful. We had a wonderful time. Would highly recommend! "