Great Oak Landing Vacation Packages
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Top Great Oak Landing Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Chestertown
Price was CA $761, price is now CA $730 per person
CA $730
per person
Apr 10 - Apr 14
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
7.2/10 Good! (415 reviews)
Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish.
Reviewed on Jan 16, 2026
Hyatt Regency Chesapeake Bay
Price was CA $1,283, price is now CA $1,259 per person
CA $1,259
per person
Apr 10 - Apr 14
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
Just as one would expect with Hyatt hotel
Great food, pool was really nice
Reviewed on Feb 16, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Price was CA $1,063, price is now CA $1,044 per person
CA $1,044
per person
Apr 10 - Apr 14
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9.2/10 Wonderful! (921 reviews)
Clean room, I enjoy staying here every time I'm in the area
Reviewed on Feb 4, 2026
Great Oak Landing Hotel Deals
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Feb 22 to Feb 23
CA $88
CA $102 total
Feb 22 - Feb 23
includes taxes & fees
7/10 Good! (1,158 reviews)
It was quiet and very clean‼️
Reviewed on Feb 10, 2026
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Feb 22 to Feb 23
CA $125
CA $147 total
Feb 22 - Feb 23
includes taxes & fees
7.8/10 Good! (1,003 reviews)
Amazing stay. 5 stars!
Reviewed on Jan 27, 2026
Hilton Garden Inn Baltimore/White Marsh
5015 Campbell Boulevard Baltimore MD
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Feb 22 to Feb 23
CA $138
CA $160 total
Feb 22 - Feb 23
includes taxes & fees
7.8/10 Good! (1,000 reviews)
The staffs were welcoming, the rooms were clean and there was enough towels. I have nothing to complain about.
Reviewed on Feb 7, 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.
Discover the most popular places to visit in Great Oak Landing
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.
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
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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.
