Great Oak Landing Vacations from $874

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The Latest Great Oak Landing vacation packages

Price found within the past 48 hours. Click for updated prices.
Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.8/10 Good! (349 reviews)
Handicap parking was one space only-for several buildings, if you stay, keep valuables off property, no security or safes are available.Staff will enter rooms without your consent or knowledge. Many of cleaning staff couldn't speak or understand english. Overall, front desk attendants are honest, professional, and well informed about area attractions and best places to visit. Beachfront rooms are nice location at boardwalk.

Reviewed on Aug 9, 2025

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
just found
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
6/10 (635 reviews)
2 minutes easy walk to the Boardwalk at the Gorgeous Beach

Reviewed on Jun 26, 2025

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (747 reviews)
Great location for activities on the beach

Reviewed on Jul 31, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.8/10 Good! (77 reviews)
Shower was very tiny. No place to sit in room other than bed.

Reviewed on Aug 3, 2025

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.4/10 Very Good! (25 reviews)
The only thing we didnt like was the living room furniture was uncomfortable

Reviewed on Aug 21, 2024

Don't see what you're looking for?
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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

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
$147 nightly
The price is $163 total per night from Aug 10 to Aug 11
$163 total
Aug 10 - Aug 11
Total includes taxes and fees
8/10 Very Good! (59 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
$56 nightly
The price is $62 total per night from Aug 17 to Aug 18
$62 total
Aug 17 - Aug 18
Total includes taxes and fees
7.2/10 Good! (1,002 reviews)
"Room was spacious and clean. Front Desk staff both checking in and checking out was unfriendly. Hotel was quiet."

Reviewed on Aug 6, 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
$79 nightly
The price is $91 total per night from Sep 1 to Sep 2
$91 total
Sep 1 - Sep 2
Total includes taxes and fees
7/10 Good! (1,004 reviews)
"Stay often due to the cost and location but the staff is unprofessional"

Reviewed on Aug 7, 2025

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
See all 354 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.

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Frequently asked questions

How much does a Great Oak Landing vacation package cost?
You'll find cheap prices from $874 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.