Great Oak Landing Trips (flight + hotel)

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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
Fully refundableReserve now, pay when you stay
The price is P7,627 per night from Aug 7 to Aug 8
P7,627
P8,466 total
Aug 7 - Aug 8
includes taxes & fees
8/10 Very Good! (57 reviews)
Great staff
"Staff was very helpful in dealing with some confusion at check in. Every on went above and beyond to deal with the situation and was very welcoming during the process."

Reviewed on Jul 28, 2025

The Lodge at Great Oak Landing
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 P3,416 per night from Aug 17 to Aug 18
P3,416
P3,826 total
Aug 17 - Aug 18
includes taxes & fees
7.2/10 Good! (1,007 reviews)
"It was fine. Quiet cable went out during storm WiFi goes in and out and all the facilities are down no pool laundry or gum"

Reviewed on Jul 31, 2025

Quality Inn & Suites Bel Air I-95 Exit 77A
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 P4,474 per night from Aug 10 to Aug 11
P4,474
P5,167 total
Aug 10 - Aug 11
includes taxes & fees
7/10 Good! (1,004 reviews)
"I loved my stay"

Reviewed on Aug 1, 2025

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
See all 353 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

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.

Washington College

Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

Wilmer Park

Crumpton Auction

Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.

Crumpton Auction

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.

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