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Browse Select Great Oak Landing Apartments

Boats docked at the marina, surrounded by a serene grassy area and wooded surroundings.

"Awesome place!"

Enjoy dining al fresco on the covered porch with a brick patio and comfortable seating.

"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "

Relax by the pool surrounded by a tranquil golf course view.

"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "

CA $219 total

includes taxes & fees

Aug 13 - Aug 14

Enjoy serene lakeside views and access to a marina with a dock perfect for boating activities.

"Everything about our stay was outstanding. Beautiful, just like the pictures show. We highly recommend this property."

Enjoy cooking in this well-equipped kitchen with a central island and bench, featuring stainless steel appliances and ample cabinetry.

"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."

Relax in a serene beach setting with a tranquil gazebo overlooking the ocean.

"Perfection"

CA $392 total

includes taxes & fees

Aug 13 - Aug 14

Enjoy cooking in this well-equipped kitchen with a central island and oven and stovetop.

"The house was clean and the beds were comfortable. "

CA $294 total

includes taxes & fees

Aug 14 - Aug 15

Relax on the balcony with wicker sofas and a small table, taking in the view of the residential street below.

"This property is near many of the downtown places you want to visit, and all are within walking distance. "

"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."

Guests can enjoy a serene lake view from the pier, surrounded by lush greenery.

"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"

CA $518 total

includes taxes & fees

Aug 12 - Aug 13

Traditional two-story house with a central entrance and a well-manicured lawn.

"Property location and size were good. Unit smelled like smoke the entire stay. "

Stroll along the paved path to a serene body of water surrounded by lush greenery.

"SMALL BUT EFFICIENT"

Enjoy cooking in this well-equipped kitchen with a large island, sink, and ample counter space.

"Nice downtown location."

Relax in a serene outdoor space with a round table and two chairs on a covered deck overlooking a natural landscape.

"Nice and quiet with a great location and amazing view!!!"

Cozy living space with a sofa, side table, and abstract art, set against a clean and contemporary backdrop.

"The apartment was very well appointed with top of the line appliances & access to the washer & dryer! We were very comfortable in this beautiful space. Thank you to the hosts for sharing your home with us!"

Work in style with a functional desk and comfortable seating area.

Relax on the waterfront patio with a bench, wicker chairs, and a shaded seating area overlooking a serene body of water.

"We couldn't have been happier with our stay. Gary and Diane were wonderful hosts, as well as their dog Lucy! They couldn't have been nicer and more accommodating, so we' are looking forward to booking another stay in the future!"