Great Oak Landing Travel Guide

Tourist 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 AU$168 per night from 18 Nov to 19 Nov
AU$168
18 Nov - 19 Nov
includes taxes & fees
Stay at this 3.5-star 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! (75 reviews)
Beautiful view

Reviewed on 8 Nov 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 AU$208 per night from 1 Dec to 2 Dec
AU$208
1 Dec - 2 Dec
includes taxes & fees
Stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
7.6/10 Good! (1,001 reviews)
The room was clean, just seemed a smidge dated. And the staff at the front desk was very courteous

Reviewed on 4 Nov 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 AU$119 per night from 9 Dec to 10 Dec
AU$119
9 Dec - 10 Dec
includes taxes & fees
Stay at this 3-star business-friendly hotel in Rosedale. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,058 reviews)
yes

Reviewed on 14 Nov 2025

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
See all 341 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.
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
Stay at this apartment in Rock Hall. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions The Mainstay and Rock Hall Harbor are located ...
10/10 Exceptional! (16 reviews)
Close to Main Street. Very nice and spacious accommodations.

Reviewed on 22 Oct 2025

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

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

Pasadena
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
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! (105 reviews)
Clean, comfortable accessible, and very responsive owner. Highly recommend :-)

Reviewed on 21 Oct 2025

First Floor Studio Apartment in Historic Chestertown
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

Enjoy the student vibe when you visit 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 browsing the exhibits at Historical Society of Kent County Maryland during your trip to 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

Enjoy the student vibe when you visit River Arts Chestertown during your trip to 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