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$223 per night from 22 Sept to 23 Sept
AU$223
22 Sept - 23 Sept
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 ...
8/10 Very Good! (68 reviews)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"

Reviewed on 5 Sept 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$190 per night from 28 Sept to 29 Sept
AU$190
28 Sept - 29 Sept
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)
"Please work on getting more elevators."

Reviewed on 9 Sept 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 AU$178 per night from 24 Sept to 25 Sept
AU$178
24 Sept - 25 Sept
includes taxes & fees
Stay at this 3-star 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! (1,010 reviews)
"everyone was so nice! and helpful! the food was good!"

Reviewed on 18 Sept 2025

Hilton Garden Inn Baltimore/White Marsh
See all 358 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.
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Annapolis
Stay at this vacation home in Annapolis. Enjoy a fitness center, laundry facilities, and in-room jetted tubs. Popular attractions Sandy Point State Park and ...
10/10 Exceptional! (2 reviews)
"We enjoyed unforgettable moments, thank you"

Reviewed on 26 July 2025

Luxury Waterfront Executive Family Home Annapolis with All Amenities
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
Book a stay at this beach vacation home in Stevensville. Enjoy free WiFi, a beach locale, and private hot tubs. Our guests praise the helpful staff in our reviews. ...
10/10 Exceptional! (181 reviews)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."

Reviewed on 2 Sept 2025

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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! (76 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 ! ! !
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

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

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

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