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 ￥19,452 per night from Sep 3 to Sep 4
￥19,452
￥21,592 total
Sep 3 - Sep 4
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! (66 reviews)
"Perfect place to unwind. Great views of the harbor and marina. You get access to a private beach and there is a cute area for kids to play. The private beach provides chairs and umbrellas. The lodge also has a bar/food on site."

Reviewed on Aug 16, 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 ￥15,701 per night from Sep 14 to Sep 15
￥15,701
￥18,449 total
Sep 14 - Sep 15
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 ...
Best Western Plus Hotel & Conference Center
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
The price is ￥8,462 per night from Sep 28 to Sep 29
￥8,462
￥9,476 total
Sep 28 - Sep 29
includes taxes & fees
Book a stay at this business-friendly hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,008 reviews)
"Great"

Reviewed on Aug 24, 2025

Quality Inn & Suites Bel Air I-95 Exit 77A
See all 356 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.
The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina

Pasadena
Stay at this cottage in Pasadena. Enjoy free WiFi, a garden, and balconies or patios. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Heron's Nest at Atlantic Marina
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! (98 reviews)
"The property was beautiful and our accommodations were wonderful. The only issue we had was nothing to do with this property. It was not easily accessible to town by foot. We went to the Chestertown Community page and asked about Uber accessibility and were told 24/7. We came to Chestertown by boat, ..."

Reviewed on Aug 25, 2025

First Floor Studio Apartment in Historic Chestertown
Waterfront Oasis w/ Private Dock, 3BR/2BA

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

Middle River
Stay at this vacation home in Middle River. Enjoy free WiFi, a garden, and patios. Popular attractions Gunpowder Falls State Park and Freestate Gun Range are ...
Waterfront Oasis w/ Private Dock, 3BR/2BA
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

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

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

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

Chestertown Dog Park

Chestertown Dog Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.

Chestertown Dog Park

Cities near Great Oak Landing

Photo by Assya A

Chestertown