Title: Visit Great Oak Landing: 2026 Travel Guide for Great Oak Landing, Chestertown | Expedia.com [Hotels in Great Oak Landing](https://expedia.com/Great-Oak-Landing-Hotels.d3000045661.Travel-Guide-Hotels)[Vacation Rentals in Great Oak Landing](https://expedia.com/Great-Oak-Landing-Vacation-Rentals.d3000045661.Travel-Guide-VacationRentals)[Car Rentals in Great Oak Landing](https://expedia.com/Car-Rentals-In-Great-Oak-Landing.d3000045661.Car-Rental-Guide)[Great Oak Landing Vacation Packages](https://expedia.com/Great-Oak-Landing.d3000045661.Destination-Travel-Guides) # Great Oak Landing, MD ## Travel Guide ## Visit Great Oak Landing Things to do - Great Oak Landing Hotel Deals - Vacation Rentals in Great Oak Landing ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 4 Philadelphia Ct Rosedale MD $74 nightly $86 total Apr 5 - Apr 6 Total with taxes and fees Book a stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ... 7/10 Good! (1,186 reviews) Excellent is all I can say about this hotel, I really enjoy my stayed there. Reviewed on Mar 30, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=3897&PinnedHotelID=3897&HadPinnedHotel=true®ionId=3000045661) ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Hotel & Conference Center 5625 O'Donnell Street Baltimore MD $107 nightly $125 total Apr 5 - Apr 6 Total with taxes and 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! (1,001 reviews) Breakfast had plenty of choices for the family. The pool was supposed to be heated and it was not the majority of the days, with ceiling tiles falling down. Reviewed on Mar 31, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=10260&PinnedHotelID=10260&HadPinnedHotel=true®ionId=3000045661) ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/6e9faa08_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn Baltimore/White Marsh 5015 Campbell Boulevard Baltimore MD $93 nightly $108 total Apr 5 - Apr 6 Total with taxes and 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! (1,008 reviews) Breakfast, was delicious. Reviewed on Mar 31, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=433663&PinnedHotelID=433663&HadPinnedHotel=true®ionId=3000045661) [See all 345 properties in Great Oak Landing](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=4%2F1%2F2026&endDate=4%2F2%2F2026®ionId=3000045661) 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. ![240' Private Beachfront @Kent Island Love Point - Great for Families](https://images.trvl-media.com/lodging/34000000/33510000/33508900/33508826/41b751bb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 240' Private Beachfront @Kent Island Love Point - Great for Families stevensville MD 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! (200 reviews) Scenic and Relaxing location. Great for families. Host was great to work with. Plan to return for another stay. Reviewed on Mar 28, 2026 [](https://expedia.com/Stevensville-Hotels-240-Private-Beachfront-Kent-Island-Love-Point-Great-For-Families.h33508826.Hotel-Information) ![Beautiful, spacious, quiet waterfront house!](https://images.trvl-media.com/lodging/61000000/60390000/60385700/60385700/c74a21f3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beautiful, spacious, quiet waterfront house! Middle River MD Stay at this vacation home in Middle River. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Miami Beach and Essex Marina are located ... 10/10 Exceptional! (57 reviews) Great waterfront home Reviewed on Jan 9, 2026 [](https://expedia.com/Middle-River-Hotels-Beautiful.h60385700.Hotel-Information) ![Waterfront Oasis w/ Private Dock, Firepit, Arcade & Sunset Views](https://images.trvl-media.com/lodging/75000000/74810000/74801000/74800974/07793f52_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Oasis w/ Private Dock, Firepit, Arcade & Sunset Views Middle River MD 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! (43 reviews) Had a great time and beautiful place on water! Reviewed on Mar 15, 2026 [](https://expedia.com/Middle-River-Hotels-Waterfront-Oasis-W-Private-Dock.h74800974.Hotel-Information) [See all properties in Great Oak Landing](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=3000045661&sort=VACATION_RENTAL) 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. ## Check Great Oak Landing hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000045661&startDate=2026-03-31&endDate=2026-04-01)[Mar 31 - Apr 1](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000045661&startDate=2026-03-31&endDate=2026-04-01) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000045661&startDate=2026-04-01&endDate=2026-03-02)[Apr 1 - Apr 2](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000045661&startDate=2026-04-01&endDate=2026-03-02) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000045661&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000045661&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000045661&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)[Apr 10 - Apr 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000045661&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026) ### Popular places to visit ![Washington College](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Washington-College-Chestertown.d553248621561000403.Vacation-Attraction) #### Rolphs Wharf Marina Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area. [](https://expedia.com/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction) #### 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. [](https://expedia.com/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) #### River Arts Chestertown Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area. [](https://expedia.com/River-Arts-Chestertown-Chestertown.d553248621532662298.Vacation-Attraction) #### Garfield Center for the Arts at the Prince Theater You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Vacation-Attraction) #### 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. [](https://expedia.com/Chestertown-Historic-District-Chestertown.d950929327394992128.Vacation-Attraction) ## Cities near Great Oak Landing ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Chestertown ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Tolchester Beach Hotels ](https://www.expedia.com/Tolchester-Beach-Hotels.d553248635975848245.Travel-Guide-Hotels) - [Worton Hotels ](https://www.expedia.com/Worton-Hotels.d3000440948.Travel-Guide-Hotels) - [Motels in Worton ](https://www.expedia.com/Worton-Motels.d3000440948-aaMotels.Travel-Guide-Accommodation) - [Edesville Hotels ](https://www.expedia.com/Edesville-Hotels.d553248635976006323.Travel-Guide-Hotels) - [Chestertown Hotels ](https://www.expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels) - [B&B in Chestertown ](https://www.expedia.com/Chestertown-Bed-And-Breakfast.d7215-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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