Great Oak Landing, MD
Travel Guide
Visit Great Oak Landing

The Lodge at Great Oak Landing
Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!
Reviewed on Sep 5, 2025

Hilton Garden Inn Baltimore/White Marsh
A very convenient and safe property close to everything we needed. Only suggestion could be to put Kurig coffee makers in the rooms if you are going to supplyKurig coffee — the coffee pods didn’t work in the coffee maker in the room.
Reviewed on Oct 25, 2025

Best Western Plus Hotel & Conference Center
We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef ...
Reviewed on Oct 26, 2025

Waterfront Oasis w/ Private Dock, 3BR/2BA
Beautiful views and the house was great. Could not figure out all the lights. Mid split did not seem to cool. Overall awesome place and great location. I would definitely stay there again. Needs a new Bbq. Overall, great place to stay.
Reviewed on Oct 9, 2025

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
We enjoyed our stay very much. The host is extremely thoughtful to ensure your stay is great. She put her own personal touch to make us feel welcome and comfortable. The place is very clean and there are a lot of amenities that they offer. Highly recommend!!
Reviewed on Oct 20, 2025

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
We enjoyed our stay. The house had plenty of room for our family with 4 adults and 1 teen. We enjoyed and used the kayaks daily. The water is dirtier than I pictured and the beach only existed for a few hours a day. The house needs a coat of paint, and clean dishes were left on the counter which ...
Reviewed on Jul 20, 2025
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Popular places to visit
Washington College
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
River Arts Chestertown
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
Historical Society of Kent County Maryland
You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
Chestertown Dog Park
Chestertown Dog Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.

