Great Oak Landing Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Great Oak Landing
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is 3.483.327 ₫ per night from 10 Jun to 11 Jun
3.483.327 ₫
3.982.487 ₫ total
10 Jun - 11 Jun
includes taxes & fees
7.8/10 Good! (86 reviews)
"This property is situated in a beautiful marina with excellent facilities. Guests staying at the Lodge can also enjoy complimentary golf, which was a great bonus. We thoroughly enjoyed our stay and would happily return. The only drawback was that the Wi-Fi service was somewhat inconsistent."
Reviewed on 6 Jun 2026
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
Fully refundableReserve now, pay when you stay
The price is 2.737.953 ₫ per night from 21 Jun to 22 Jun
2.737.953 ₫
3.217.141 ₫ total
21 Jun - 22 Jun
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"It was a clean ,friendly place , had a bar and prices very reasonable ,the complimentary breakfast was awesome , had a lot more food than other places ,did not have to get out till noon"
Reviewed on 2 Jun 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is 2.253.762 ₫ per night from 29 Jun to 30 Jun
2.253.762 ₫
2.603.095 ₫ total
29 Jun - 30 Jun
includes taxes & fees
7/10 Good! (1,213 reviews)
"Crean room"
Reviewed on 7 Jun 2026
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.
Popular places to visit
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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.
Garfield Center for the Arts at the Prince Theater
You can make plans for a show at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
