Great Oak Landing Vacations from $794

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The Latest Great Oak Landing Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Shore Point Cottages

Shore Point Cottages

3 out of 5
per person
Aug 5 - Aug 8
found 14 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9.2/10 Wonderful! (59 reviews)
This was a really nice place to stay. I loved the keyless entry. I loved the way the little cottage was laid out. It had a modern and cozy flow. It was so nice being able to sit out on the front porch and not worry about bugs coming in because of the whole thing being screened in. The pool area was fantastic as well with a large pool, lounge chairs, tables with umbrellas and a restroom. The only thing that was odd to me was the fact that there was no host on site. But other then that it was wonderful and I would totally come back. My husband wanted to move there lol.

Reviewed on Jun 7, 2024

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Aug 5 - Aug 8
found 14 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.8/10 Excellent! (2,022 reviews)
I loved the fact they were dog friendly,the balcony view of the beach was beautiful.Our room was everything I expected it to be.The hotel had so many different options to offer it was excellent!!!The breakfast restaurant on the 6th floor was everything!!! I will be coming back!!! Thank You for everything💐👏

Reviewed on Jun 7, 2024

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

2.5 out of 5
Downtown Ocean City
per person
Aug 5 - Aug 8
found 14 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.4/10 Very Good! (7 reviews)
The receptionist was excellent, she was very helpful and understanding.

Reviewed on Jun 2, 2024

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
per person
Aug 5 - Aug 8
found 14 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.6/10 Excellent! (1,007 reviews)
My room smelled musty. Stains on carpet. Great location near boardwalk. Wouldn’t stay again. The elevator kept jerking the entire time there, it was concerning! Spend the extra money and go somewhere else better.

Reviewed on Jun 6, 2024

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
per person
Aug 5 - Aug 8
found 14 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
7.8/10 Good! (1,809 reviews)
Pool and being close to ocean.

Reviewed on Jun 5, 2024

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

Great Oak Landing Hotel Deals

The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is $132 per night from Jun 10 to Jun 11
$132
$151 total
includes taxes & fees
Jun 10 - Jun 11
7.6/10 Good! (4 reviews)
Middle of nowhere
"The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time."

Reviewed on Oct 6, 2023

The Lodge at Great Oak Landing
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
The price is $98 per night from Jul 7 to Jul 8
$98
$115 total
includes taxes & fees
Jul 7 - Jul 8
7.6/10 Good! (1,009 reviews)
"The staff was very helpful and friendly"

Reviewed on Jun 6, 2024

Best Western Plus Hotel & Conference Center
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
2.5 out of 5
4 Philadelphia Ct, Rosedale, MD
Fully refundableReserve now, pay when you stay
The price is $84 per night from Jul 4 to Jul 5
$84
$97 total
includes taxes & fees
Jul 4 - Jul 5
7.2/10 Good! (1,013 reviews)
"Breakfast could be better. Other than that, my stay was great. This is a very dog friendly hotel. Cool!!"

Reviewed on Jun 7, 2024

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
See all 310 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.

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?
Get ready to book, because a getaway to Great Oak Landing starts from an enticing $794. When you bundle your hotels, flights and car rentals into a travel package, you’ll score the lowest prices.
How do I get a cheap travel package to Great Oak Landing?
It’s as simple as bundling. Flights, rental cars and hotels — combine whatever you need into a Great Oak Landing vacation package to save a pile of cash. Score even better deals when you include extras such as experiences or tours to your booking. But that’s not the only impressive part. You have the flexibility to put together your trip your own way. We offer more than 550 airlines and 1,000,000 hotels all over the world, so that everyone has an opportunity to travel and fulfill those vacation dreams.
What are the top hotels in Great Oak Landing?
If it’s comfort and convenience you’re searching for, you won’t beat Great Oak Manor. Spend your evenings kicking back here and your days exploring Great Oak Landing’s finest sights.
How far in advance should I book my Great Oak Landing vacation?
It depends on the airline, but it’s usually possible to browse through international airfares on Expedia nearly a year in advance. While it’s a good idea to book ahead of time, lucky customers will occasionally score a cheaper ticket just weeks before departure dates.
What does an Expedia Great Oak Landing travel package include?
Select from any combination of flights, hotels and rental cars. Once you’ve made your booking, you can add the fun stuff like activities and tours. Want to pick your fare class? That’s easy to do too. The choice is yours when it comes to creating your perfect Great Oak Landing escape.
What should I know before booking a Great Oak Landing travel package?
You can save a tidy sum by combining your hotels, flights and rental cars. Once you’ve made your booking, you can add on things like sightseeing tours or experiences. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a Great Oak Landing Expedia vacation package?
Yes, definitely. Expedia has over 550 partner airlines to choose from around the world. With so many choices, finding the ideal carrier to fly you to Great Oak Landing won’t be difficult.
If I'm not able to travel, can I cancel my Great Oak Landing vacation package?
Don’t stress if you’re rethinking your Great Oak Landing vacation package — it’s possible to cancel or amend your booking. And if you’ve booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We realize your circumstances can change suddenly, so head to our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll be here to help.

Discover the most popular places to visit in Great Oak Landing

Image for 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
Image for Rolphs Wharf Marina

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
Image for River Arts Chestertown

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

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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.