Great Oak Landing Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Great Oak Landing Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sahara Motel
Downtown Ocean City
Price was CA $2,098, price is now CA $1,570 per person
CA $1,570
per person
Jul 19 - Jul 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
7.6/10 Good! (550 reviews)
The only upside of this motel was the location. The motel was pretty outdated, not clean as I expected, and there is no discount on breakfast especially due to staying at the motel and there being a breakfast spot apart of the motel with the same name. If you are looking for a one night stay close to the beach, with free parking for just one night than fine. But I definitely would not been able to stay any longer. The motel needs some updating, the walls did to be wiped down, and they need new carpet. When entering the room there was a smoke/ old weird smell I can’t even explain.
Reviewed on Jun 1, 2026
Fenwick Shores, Tapestry Collection by Hilton
Price was CA $4,198, price is now CA $3,074 per person
CA $3,074
per person
Jul 19 - Jul 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
9.6/10 Exceptional! (764 reviews)
Love this hotel! Has everything I need, great location and love the space!
Reviewed on May 27, 2026
Ocean Terrace Family Apartments
Downtown Ocean City
Price was CA $2,852, price is now CA $2,140 per person
CA $2,140
per person
Jul 19 - Jul 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
8/10 Very Good! (31 reviews)
The unit was outdated, small, and had mismatched and old furniture. The shower in one of our bathrooms wouldn’t drain. The oven did not work. There was only one television. Concerns couldn’t be communicated because the staff hardly spoke English (although they were very nice).
The unit was in a really nice location - 1.5 blocks from the boardwalk and beach. We liked the outside showers.
Reviewed on Aug 9, 2025
Lankford Hotel and Lodge
Downtown Ocean City
Price was CA $2,225, price is now CA $1,712 per person
CA $1,712
per person
Jul 19 - Jul 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
8.6/10 Excellent! (642 reviews)
This was an amazingly quirky place that would be so awesome for a couple days. We had 2 bedrooms, kitchenette/dining room and bath. I loved the artwork, the little porch and how close we were to the boardwalk. The bathroom was tiny and the shower didn't work, but we were the first guest for the season in that unit, so they didn't know it wasn't working. They were very responsive and everything was clean. If I was planning to spend 3 or more days in town, this would be a good choice.
Reviewed on May 5, 2026
Bay Club Resort by Coolvacay
Midtown Ocean City
Price was CA $4,000, price is now CA $3,083 per person
CA $3,083
per person
Jul 19 - Jul 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
8.4/10 Very Good! (39 reviews)
Beautiful place that aided to my family having a great vacation! 10/10 and I’d definitely stay there again!
Reviewed on May 31, 2026
Great Oak Landing Hotel Deals
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
The price is CA $182 per night from Jun 9 to Jun 10
CA $182
CA $209 total
Jun 9 - Jun 10
includes taxes & fees
7.8/10 Good! (83 reviews)
"There is a pool but no life guard. The restaurant is closed. No breakfast. You have to make your own coffee. The room was clean but a little damp. Nobody in the office after 5. The beds were comfortable, the view of the sunset over the bay was fabulous. We got carry-out and ate at the outdoor seating. ..."
Reviewed on May 28, 2026
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Jun 7 to Jun 8
CA $166
CA $195 total
Jun 7 - Jun 8
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Excellent place to stay. Great complimentary breakfast, nice large parking lots for vehicles with trailers. Clean rooms, fast check in. Could not be happier. Excellent rates as well"
Reviewed on Jun 1, 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 Jul 2 to Jul 3
CA $138
CA $160 total
Jul 2 - Jul 3
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Checked into room only to find out the plumbing at the hotel was being worked on and there was no water until later in our rooms. Once the water came on, it was brown until the next morning. Out relatives had to change rooms because their toilet was not working and the room smelled like sewage. I ..."
Reviewed on May 31, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
