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
3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is AED 441 per night from Apr 21 to Apr 22
AED 441
AED 489 total
includes taxes & fees
21 Apr - 22 Apr
7.6/10 Good! (47 reviews)
Respite
"Generally okay, Clean but property could use some upgrade"

Reviewed on 27 October 2024

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 AED 386 per night from Apr 27 to Apr 28
AED 386
AED 453 total
includes taxes & fees
27 Apr - 28 Apr
7.6/10 Good! (1,004 reviews)
"Great staff, onsite free parking and close to downtown area."

Reviewed on 19 April 2025

Best Western Plus Hotel & Conference Center
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
2.5 out of 5
4 Philadelphia Ct, Rosedale, MD
Fully refundableReserve now, pay when you stay
The price is AED 297 per night from Apr 21 to Apr 22
AED 297
AED 343 total
includes taxes & fees
21 Apr - 22 Apr
6.8/10 (1,005 reviews)
"I like the nice employees how they made everything easy to check in"

Reviewed on 15 April 2025

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
See all 341 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 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.

Discover the most popular places to visit in Great Oak Landing

Washington College

4/5(13 reviews)

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.

Washington College

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.

Historical Society of Kent County Maryland

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