Great Oak Landing Vacations from $671

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The Latest Great Oak Landing Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern outdoor seating area with striped sofas and a central fire pit.
    Jan 15 - Jan 19

    Fenwick Shores, Tapestry Collection by Hilton + Flight

    Fenwick Island
    4 nights
    3.5 star property
    9.4/10 - Exceptional (883 reviews)
    Roundtrip • Los Angeles (LAX) - Salisbury (SBY)
    LAX - SBY • 1 stop SBY - LAX • 2 stops
    $772
    $671
    per traveler
    found 1 day ago
    Fenwick Shores, Tapestry Collection by Hilton
  • A balcony with a view of the sea, palm trees, and a wooden railing.
    Jan 15 - Jan 19

    Oceanic Motel + Flight

    Downtown Ocean City
    4 nights
    2.0 star property
    7.0/10 - Good (851 reviews)
    Roundtrip • Los Angeles (LAX) - Salisbury (SBY)
    LAX - SBY • 1 stop SBY - LAX • 1 stop
    $2,744
    $2,103
    per traveler
    found 3 hours ago
    Oceanic Motel
  • A reception desk with a wooden sign reading "WELCOME TO THE BEACH," a red telephone, a lamp, and a clock on the wall.
    Dec 24 - Dec 27

    Beach Walk + Flight

    Downtown Ocean City
    3 nights
    2.0 star property
    7.6/10 - Good (128 reviews)
    "We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel."
    Reviewed October 13, 2026
    Roundtrip • New York (NYC) - Salisbury (SBY)
    JFK - SBY • 1 stop SBY - EWR • 1 stop
    $2,567
    $1,974
    per traveler
    found 1 day ago
    Beach Walk
  • A reception desk with a logo and name "The Shore House" on the wall.
    Jan 15 - Jan 19

    The Shore House + Flight

    West Ocean City
    4 nights
    2.0 star property
    6.6/10 - (843 reviews)
    Roundtrip • Los Angeles (LAX) - Salisbury (SBY)
    LAX - SBY • 1 stop SBY - LAX • 1 stop
    $2,459
    $2,126
    per traveler
    found 3 hours ago
    The Shore House
  • A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
    Jan 15 - Jan 19

    Hyatt Place Ocean City / Oceanfront + Flight

    Downtown Ocean City
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,872 reviews)
    Roundtrip • Los Angeles (LAX) - Salisbury (SBY)
    LAX - SBY • 1 stop SBY - LAX • 2 stops
    $819
    $718
    per traveler
    found 1 day ago
    Hyatt Place Ocean City / Oceanfront

Great Oak Landing Hotel Deals

A campfire in a stone fire pit by a lakeside at sunset.

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
0.2 mi from Great Oak Landing
8.0 out of 10, Very good, (127 reviews)
"Unique place to stay while visiting in Chestertown. 2nd floor only stair accessible. But, nice stay. Beautiful view of the marina when we awoke."
$124 nightly
The price is $137
Nov 8 - Nov 9
Total with taxes and fees
The Lodge at 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.
See all properties in Great Oak Landing

Frequently Asked Questions

How much does a Great Oak Landing vacation package cost?

You'll find cheap prices from $671 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.

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