Great Oak Landing Vacations

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Find the Best Great Oak Landing Vacation Packages

Great Oak Landing Hotel Deals

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is ￥21,390 per night from Jul 14 to Jul 15
￥21,390
￥24,456 total
Jul 14 - Jul 15
includes taxes & fees
7.8/10 Good! (90 reviews)
"We love this place 😀….great pool nice room,free golf!!!!….in the middle of nowhere,but that’s nice…15 minutes to Chestertown…we come every year 👍"

Reviewed on Jul 7, 2026

The Lodge at Great Oak Landing
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
Fully refundableReserve now, pay when you stay
The price is ￥12,805 per night from Jul 19 to Jul 20
￥12,805
￥14,789 total
Jul 19 - Jul 20
includes taxes & fees
7/10 Good! (1,222 reviews)
"Mo elevators were working"

Reviewed on Jul 10, 2026

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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 ￥16,813 per night from Jul 20 to Jul 21
￥16,813
￥19,756 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very Good! (1,005 reviews)
"Only thing was would not let delivery come to room when was ready for bed-- I don't understand why. Convenient for customers when relaxing in room"

Reviewed on Jul 10, 2026

Best Western Plus Hotel & Conference Center
See all 346 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.

Frequently asked questions

How much does a Great Oak Landing vacation 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 vacation 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 vacation 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 vacation 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 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.
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 personalized Great Oak Landing vacation package.

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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.