Great Oak Landing Vacations from $1,536

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The Latest Great Oak Landing vacation packages

Price found within the past 48 hours. Click for updated prices.
Americana Condos 10th street

Americana Condos 10th street

3.5 out of 5
Downtown Ocean City
Price was $1,971, price is now $1,536 per person
$1,536
per person
Jun 26 - Jun 30
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
8.4/10 Very Good! (19 reviews)
straight fire, definitely going back

Reviewed on Jun 21, 2025

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $2,064, price is now $1,562 per person
$1,562
per person
Aug 13 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.6/10 Excellent! (1,196 reviews)
We stayed in a beach front room. Excellent views. Room was comfortable. A/C was only a fan one night but was fixed in the morning. Fortunately, it wasn't hot outside. When we arrived, there was a used towel on the back of the bathroom door. You can tell housekeeping cut corners and wasn't thorough and we never got wash clothes unless we went to the front desk and asked. Weird. All in all, we enjoyed our stay and we're comfortable. Parking is tight and they have an overflow lot a block away. Convenient to eateries, bars, and shopping. Tiny indoor pool (we didn't use). Less than 10 miles to Assateague Island. You can go up the coast and see Fenwick Island, Bethany Beach, Dewey Beach and Rehoboth Beach easily. Awesome sunrises!!

Reviewed on May 22, 2026

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $2,026, price is now $1,562 per person
$1,562
per person
Aug 13 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.2/10 Very Good! (720 reviews)
Clean room. Nice staff, great location on the boardwalk.

Reviewed on May 13, 2026

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $2,851, price is now $2,213 per person
$2,213
per person
Aug 13 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.4/10 Very Good! (39 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $2,420, price is now $1,912 per person
$1,912
per person
Aug 13 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
9/10 Wonderful! (3,574 reviews)
The Ocean front view was great. The size of the room and terrace was big.

Reviewed on May 23, 2026

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Discover the most popular places to visit in Great Oak Landing

Washington College

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

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

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

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
$141 nightly
The price is $157 total per night from Jun 9 to Jun 10
$157 total
Jun 9 - Jun 10
Total with taxes and fees
8/10 Very Good! (82 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again"

Reviewed on May 18, 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
$75 nightly
The price is $87 total per night from May 31 to Jun 1
$87 total
May 31 - Jun 1
Total with taxes and fees
7/10 Good! (1,204 reviews)
"Saturday night very disruptive."

Reviewed on May 23, 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
$107 nightly
The price is $125 total per night from May 31 to Jun 1
$125 total
May 31 - Jun 1
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"I couldn't connect to the Internet. I stayed 2 prior stays and couldn't connect as well. It isn't my computer either. Had to use hotspot from my phone to do business."

Reviewed on May 22, 2026

Best Western Plus Hotel & Conference Center
See all 349 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.

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 $1,536 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.