Great Oak Landing Vacations from $696
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The Latest Great Oak Landing vacation packages
Price found within the past 48 hours. Click for updated prices.
Fenwick Shores, Tapestry Collection by Hilton
Save 100% on your flight
Price was $1,410, price is now $1,059 per person
$1,059
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
9.6/10 Exceptional! (757 reviews)
Beautiful property near the beach. Quiet neighborhood. Smaller hotel which is what we like!! Front desk was great to help us with an earlier check out! Only disappointment was room service never came into our room on a Tues-Fri stay. (Of course we never said anything and we could have.) Also, would’ve been nice if ACTUAL or UPDATED hours were posted on the restaurant and bars. You never knew if/when they’d be open. Again, great hotel but definitely had slipped since we were there 2 years ago.
Reviewed on May 25, 2026
The Americana Hotel
Downtown Ocean City
Price was $1,297, price is now $988 per person
$988
per person
Aug 19 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Salisbury (SBY)
8.6/10 Excellent! (1,196 reviews)
EVERYONE OF STAFF WAS ON POINT AND TOOK CARE OF NEEDS AND THEY WERE THERE FOR ME. I WILL BE BACK AGAIN IN JULY FOR INDEPENDENCE DAY THIS SUMMER THANK YOU.
Reviewed on May 25, 2026
Ocean 1 Hotel and Suites
Downtown Ocean City
Price was $1,375, price is now $1,071 per person
$1,071
per person
Aug 19 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Salisbury (SBY)
8.2/10 Very Good! (720 reviews)
Clean room. Nice staff, great location on the boardwalk.
Reviewed on May 13, 2026
Bethany Beach Ocean Suites Residence Inn by Marriott
Downtown Bethany Beach
Price was $3,382, price is now $2,675 per person
$2,675
per person
Jul 10 - Jul 17
found 20 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Salisbury (SBY)
9/10 Wonderful! (822 reviews)
A beautiful place to stay with an amazing beach view. Rooms are spacious and clean but it would be nice to have a broom in each room to sweep up sand. The breakfast buffet was amazing! The only downside was having to pay $40 a day to park in the parking garage or pay by meter if you didn’t want to park in the garage.
Reviewed on May 23, 2026
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See all available trips from Columbus to Great Oak Landing
View all tripsDiscover 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.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
River Arts Chestertown
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
Great Oak Landing Hotel Deals
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
$142 nightly
The price is $158 total per night from May 27 to May 28
$158 total
May 27 - May 28
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
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from May 31 to Jun 1
$85 total
May 31 - Jun 1
Total with taxes and fees
7/10 Good! (1,206 reviews)
"The elevator wasn’t working. I’m disabled and my room was on the 3rd floor. The lobby smells terrible. Idk if it was the staffs body odor or what. Terrible. Smell. Rest of the hotel and room smelled fresh but heavily masked by spray and product but ok. Breakfast area smelled like mold and waffles. ..."
Reviewed on May 24, 2026
Best Western Plus Hotel & Conference Center
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! (1,005 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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.