Search Condo Rentals in Great Oak Landing

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

BEACH WITHOUT THE BUSTLE

10.0 out of 10, Exceptional, (26)
"We enjoyed our stay. Condo was comfortable and very clean. It provided convenient access for our weekend plans in Kennedyville and Chestertown."
BEACH WITHOUT THE BUSTLE

Kent Island Waterfront Cottage

9.2 out of 10, Wonderful, (7)
"My husband and I stayed here for a quick weekend getaway to celebrate our anniversary. We appreciated the host being able to accommodate us an earlier check in and later check out time to maximize our short time away. They only charged us a small fee. The place was clean. So clean that I didn't feel I needed to wipe anything down, which is usually the case when we go to other places. The view was stunning and we had nice weather. We loved being able to walk out onto the dock as well as sit out...
Kent Island Waterfront Cottage

Unobstructed view of the Chesapeake Bay, w/ a beach!

10.0 out of 10, Exceptional, (19)
"This property is beautiful and relaxing. The view of the sassafrass is very peaceful, its fun to watch the boats go by, and watch the joy of people at the beach. The place has everything you could want. It’s comfortable, clean, and relaxing. We had a wonderful time, and hope to come back one day. Very much recommend it for your stay in the area. "
Unobstructed view of the Chesapeake Bay, w/ a beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Great Oak Landing
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Great Oak Landing

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (75)
"EasyvPeasy place."
The price is HK$763
HK$1,228 total
includes taxes & fees
30 Nov - 1 Dec
First Floor Studio Apartment in Historic Chestertown

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.8 out of 10, Exceptional, (26)
"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...
Waterfront Oasis w/ Private Dock, 3BR/2BA

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.

Frequently asked questions

Why book your condo in Great Oak Landing with Expedia?
Booking a condo in Great Oak Landing is as easy as entering your travel dates and picking the option that suits your needs. Want something affordable or luxurious, or a stay that also features free WiFi? Use Expedia’s search filters to further narrow your search results and find your ideal pad.
How can I find cheap condos in Great Oak Landing?
Expedia can help you search for cheap condos in Great Oak Landing. To find a fantastic stay in a couple of quick clicks, use our handy filter tool to tailor your search results by star rating, amenities and budget.