Great Oak Landing Vacations from $599

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Great Oak Landing vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

2.5 out of 5
Midtown Ocean City
Price was $643, price is now $599 per person
$599
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) to Salisbury (SBY)
8.8/10 Excellent! (1,002 reviews)
All was awesome. Staff helpful and friendly!

Reviewed on Nov 6, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,178, price is now $1,914 per person
$1,914
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) to Salisbury (SBY)
7.6/10 Good! (89 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing

Reviewed on Oct 17, 2025

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $861, price is now $795 per person
$795
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) to Salisbury (SBY)
8.8/10 Excellent! (1,008 reviews)
The room was spotless. The staff were courteous and helpful. Fantastic hotel!

Reviewed on Oct 28, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $668, price is now $622 per person
$622
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) to Salisbury (SBY)
9/10 Wonderful! (3,258 reviews)
Update rooms needed quality of food for breakfast when you ask for banana walnut pancakes and get one slice of banana on top it didn’t fit the picture shown & room smelled musty?

Reviewed on Nov 12, 2025

Motel 6 Salisbury, MD

Motel 6 Salisbury, MD

2 out of 5
Price was $711, price is now $663 per person
$663
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) to Salisbury (SBY)
7.2/10 Good! (925 reviews)
The room was clean and relaxing this has been our second time here and everything was good

Reviewed on Nov 9, 2025

Don't see what you're looking for?
See all available trips from Columbus to Great Oak Landing
View all trips

Discover the most popular places to visit in Great Oak Landing

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

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

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

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
$113 nightly
The price is $126 total per night from Nov 16 to Nov 17
$126 total
Nov 16 - Nov 17
Total with taxes and fees
7.8/10 Good! (75 reviews)
Beautiful view

Reviewed on Nov 8, 2025

The Lodge at Great Oak Landing
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard, Baltimore, MD
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $106 total per night from Nov 16 to Nov 17
$106 total
Nov 16 - Nov 17
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
Clean definitely recommend

Reviewed on Nov 9, 2025

Hilton Garden Inn Baltimore/White Marsh
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
$63 nightly
The price is $71 total per night from Nov 16 to Nov 17
$71 total
Nov 16 - Nov 17
Total with taxes and fees
7.2/10 Good! (1,011 reviews)
Nice room

Reviewed on Nov 11, 2025

Quality Inn & Suites Bel Air I-95 Exit 77A
See all 339 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Great Oak Landing vacation package cost?
You'll find cheap prices from $599 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.

Explore a world of travel with Expedia

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