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 ￥15,456 per night from Dec 28 to Dec 29
￥15,456
￥17,671 total
Dec 28 - Dec 29
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! (77 reviews)
Beautiful view

Reviewed on Nov 8, 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 ￥13,893 per night from Jan 4 to Jan 5
￥13,893
￥16,325 total
Jan 4 - Jan 5, 2026
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 ...
7.8/10 Good! (1,000 reviews)
room is big and clean. Breakfast was good

Reviewed on Dec 14, 2025

Best Western Plus Hotel & Conference Center
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
The price is ￥16,455 per night from Jan 2 to Jan 3
￥16,455
￥19,006 total
Jan 2 - Jan 3, 2026
includes taxes & fees
Book a stay at this family-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.8/10 Good! (1,002 reviews)
Clean Rooms, Nice Staff...good area with many restaurant choices.

Reviewed on Dec 19, 2025

Hilton Garden Inn Baltimore/White Marsh
See all 345 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)
Great space and location. Well equipped kitchen, maybe a bit too many pans etc. Cleaning could be a bit better. This is our second time at the property, so we definitely like it!

Reviewed on Nov 30, 2025

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome

2 out of 5
Rosedale Maryland
Stay at this vacation home in Rosedale. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions White Marsh Mall and Essex Marina are ...
Close to Hospital & White Marsh! Rosedale Townhome
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall MD
Book a stay at this family-friendly villa in Rock Hall. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Rock Hall Harbor and The Mainstay ...
9.8/10 Exceptional! (40 reviews)
We had an absolutely amazing stay. It was the PERFECT back drop for our October wedding. The weather was perfect and the indoor outdoor feel was so luxurious. We could not be more grateful for the excellent bedrooms for our guests to stay in. The amenities were very much appreciated. Plenty of towels, ...

Reviewed on Oct 19, 2025

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
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

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

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

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

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

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

Crumpton Auction

Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.

Crumpton Auction

Cities near Great Oak Landing

Photo by Assya A

Chestertown