Great Oak Landing Holidays

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Top hotels in Great Oak Landing

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 €126 per night from 24 Aug to 25 Aug
€126
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (65 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 16 Aug 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
Fully refundableReserve now, pay when you stay
The price is €108 per night from 7 Sept to 8 Sept
€108
7 Sept - 8 Sept
includes taxes & fees
7.6/10 Good! (1,000 reviews)
"Great"

Reviewed on 17 Aug 2025

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
Fully refundableReserve now, pay when you stay
The price is €52 per night from 7 Sept to 8 Sept
€52
7 Sept - 8 Sept
includes taxes & fees
7.2/10 Good! (1,008 reviews)
"Room was nice , clean, spacious. Area was good. Dennys , Waffle House, close by. Breakfast is only waffles, yogurt , cereal and coffe"

Reviewed on 17 Aug 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.

Popular places to visit

Garfield Center for the Arts at the Prince Theater

You can make plans for a show 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.

Garfield Center for the Arts at the Prince Theater

Frequently asked questions

How much does a Great Oak Landing holiday package cost?
You'll find cheap prices on Expedia for your Great Oak Landing getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your holiday to Great Oak Landing costs.
What are the cheapest months to go to Great Oak Landing?
The off-season is the best time to travel to Great Oak Landing if you're on a budget. Another tip for getting cheap Great Oak Landing holiday packages? Try to avoid visiting during public holidays and any major festivals or events.
How many days is enough for Great Oak Landing?
The ideal length of your Great Oak Landing holiday depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to visit all the major attractions and discover some hidden spots along the way.
How to find the best Great Oak Landing package deals?
Begin your search for a Great Oak Landing package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Great Oak Landing package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Great Oak Landing escape underway.
Is it cheaper to book a Great Oak Landing holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can tailor your Great Oak Landing escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Great Oak Landing?
If you have your Great Oak Landing travel dates confirmed, book as soon as you can to score some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Great Oak Landing?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Great Oak Landing.
  2. Plan your budget wisely: Besides the cost of your stay, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that could arise during your trip to Great Oak Landing.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to get to in Great Oak Landing. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Great Oak Landing holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.