Great Oak Landing Vacations from $717
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The Latest Great Oak Landing vacation packages
Price found within the past 48 hours. Click for updated prices.
Sea Bay Hotel
Midtown Ocean City
$2,250
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
8.2/10 Very Good! (673 reviews)
The housekeeping staff were very pleasant the parking was easily accessible the room was very neat and comfortable the balcony was very nice to sit on
Reviewed on Sep 20, 2026
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The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
$124 nightly
$137 total
Sep 23 - Sep 24
Total with taxes and fees
8/10 Very Good! (111 reviews)
"We loved this marina motel lodge. It has a beautiful view of the bay and boats. The restaurant was closed as it was a bit out of season but the landscape and beauty of the bay is exquisite. It is well-maintained but could use some freshening up. We would definitely return as we loved the location ..."
Reviewed on Sep 20, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
$71 nightly
$82 total
Sep 27 - Sep 28
Total with taxes and fees
7/10 Good! (1,241 reviews)
"Clean room"
Reviewed on Sep 19, 2026
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
Fully refundableReserve now, pay when you stay
$107 nightly
$125 total
Sep 28 - Sep 29
Total with taxes and fees
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.
Find the Best Great Oak Landing Vacation Packages
Great Oak Landing Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Top Sights | Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Washington College |
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Frequently asked questions
How much does a Great Oak Landing vacation package cost?
You'll find cheap prices from $717 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 vacation to Great Oak Landing costs.
What are the cheapest months to go to Great Oak Landing?
You're likely to find reduced prices and greater availability in May, November and December. Take a look at our cheap Great Oak Landing vacation packages and you could land some great off-season deals.
How many days is enough for Great Oak Landing?
The ideal length of your Great Oak Landing vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to tick off all the major sights and discover some hidden treasures 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 vacation as a package?
An Expedia vacation 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 vacation 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 traveling on a whim.
Does Expedia offer Book Now, Pay Later Great Oak Landing vacation packages?
Jet off on your perfect escape to Great Oak Landing with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until the next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up cheap deals while they last.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
