Great Oak Landing, MD

Travel Guide

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
The price is AED 364 per night from Nov 24 to Nov 25
AED 364
AED 416 total
24 Nov - 25 Nov
includes taxes & fees
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
7.8/10 Good! (76 reviews)
Beautiful view

Reviewed on 8 November 2025

The Lodge at Great Oak Landing
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
The price is AED 392 per night from Dec 1 to Dec 2
AED 392
AED 461 total
1 Dec - 2 Dec
includes taxes & fees
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,002 reviews)
The hotel was clean and staff were pleasant, accomodating and friendly

Reviewed on 20 November 2025

Best Western Plus Hotel & Conference Center
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
The price is AED 238 per night from Dec 8 to Dec 9
AED 238
AED 275 total
8 Dec - 9 Dec
includes taxes & fees
Book a stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,069 reviews)
Nice and clean

Reviewed on 21 November 2025

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
See all 344 properties in Great Oak Landing
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.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena MD
Book a stay at this beach vacation home in Pasadena. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Downs Park Dog Beach and Fort Smallwood ...
9.2/10 Wonderful! (77 reviews)
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 20 July 2025

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown MD
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
9.6/10 Exceptional! (106 reviews)
Everything was clean and neat and welcoming

Reviewed on 12 November 2025

First Floor Studio Apartment in Historic Chestertown
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Chestertown MD
Stay at this vacation home in Chestertown. Enjoy laundry facilities and air conditioning. Popular attractions Garfield Center for the Arts at the Prince Theater ...
10/10 Exceptional! (1 review)
Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!

Reviewed on 26 October 2025

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
See all properties in Great Oak Landing
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

Washington College

4/5(13 reviews)

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.

Washington College

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

Rolphs Wharf Marina

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.

Historical Society of Kent County Maryland

Chestertown Historic District

Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene.

Chestertown Historic District

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

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.

Wilmer Park