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“We truly enjoyed our stay at Osprey’s Landing. Check-in and check-out were smooth. The property and grounds were awesome. We especially loved the pool, beach area, playground, views, and convenient location. We hope to return in the future!”

“The property was beautiful and our accommodations were wonderful. The only issue we had was nothing to do with this property. It was not easily accessible to town by foot. We went to the Chestertown Community page and asked about Uber accessibility and were told 24/7. We came to Chestertown by boat, no vehicle. We had a 2 mile walk to town to get something to eat. ”

“Great place. Well organized and really nice host.”

“As others have noted, the space is very clean, well appointed and conveniently located. I'd like to add that the hosts have done a wonderful job of representing the community in the home. Their art collection is lovely and features local artists. The books placed are all interesting and about the area; even the chocolates were purchased from a locally owned store. I would absolutely stay here again and highly recommend it.”

“I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! ”

“In town for the Annapolis Sailboat Show. It was the perfect location. Easy walking distance to downtown and tons of bars and restaurants. Property manager is quick to respond to communication, and was extremely helpful returning a lost item. The property is very nicely updated and was extremely comfortable. It had absolutely everything we needed in the perfect spot!”

“My husband and I were there for our anniversary weekend. Hosts were very friendly, had good recommendations, and place was modern and clean! We enjoyed the beach area, sunsets and walks in the neighborhood. We brought our own kayaks and fished... caught lots of catfish!! We brought our bikes for Chesapeake City.We enjoyed the Bohemia Manor Winery nearby. Great sunsets and great memories! Thanks again! ”

“Thanks for having such a cute place! It was a great central location to all that we wanted to do while in Delaware/east coast for a Lacrosse tourney! ”