Great Oak Landing

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 €97 per night from 18 Nov to 19 Nov
€97
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 €117 per night from 1 Dec to 2 Dec
€117
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! (1,003 reviews)
First I would like to thank you'll for great customer service and hospitality. All the employees were very respectful. I do have a few concerns regarding the room. I paid 700$ for the weekend based on the amenities and to celebrate my 20th year anniversary . My main concern is the jacuzzi tub. The ...

Reviewed on 12 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 €67 per night from 9 Dec to 10 Dec
€67
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! (1,059 reviews)
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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.
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 Jul 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)
Everything was clean and neat and welcoming

Reviewed on 12 Nov 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 CopperPlex and Miami Beach are located nearby.
9.4/10 Exceptional! (38 reviews)
An older house but still nice and pet friendly. Rugs and carpet needed cleaning.

Reviewed on 26 Oct 2025

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

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