Name: The Lodge at Great Oak Landing
Price range: CA $187
Rating: 7.8

Your Chestertown Vacation

There's no better way to embark on an adventure than with one of our vacation packages to Chestertown. The colonial history and cultural experiences are just two of the countless reasons to spend some time in this captivating city. Fill your free time with visits to Washington College, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater, some of the things you simply have to see during a trip to Chestertown. A couple of quick clicks is all it takes to put together a tailor-made Chestertown vacation on Expedia.

Top Chestertown Vacation Deals

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

Eden Roc Motel

Downtown Ocean City

CA $760

per person

Sep 3 - Sep 7

found 18 hours ago

Roundtrip flight included

Montreal (YMQ) to Salisbury (SBY)

7.6/10 Good! (17 reviews)

The room I reserved was over booked, so they upgraded me to one of their 2 bed room apartments for no extra charge, and they allowed me to check in the following day, because I was arriving after check in time. Just leaving my apartment unlocked with a key and note on the kitchen counter. Very nice, only complaint I really had was that the floor was wooden and could of been cleaned better. After my friend got out of the shower, she walked around bare foot and the bottoms of her feet ended up being black with in 5 minutes. Thankfully for me I wear slides all the time so I didn't have that issue.

Reviewed on Jun 22, 2026

Harrison Hall Hotel

Downtown Ocean City

CA $868

per person

Sep 3 - Sep 7

found 18 hours ago

Roundtrip flight included

Montreal (YMQ) to Salisbury (SBY)

7.4/10 Good! (1,010 reviews)

Enjoyed our stay clean rooms,friendly staff and great location

Reviewed on Jun 22, 2026

Dunes Court

Midtown Ocean City

CA $815

per person

Sep 3 - Sep 7

found 18 hours ago

Roundtrip flight included

Montreal (YMQ) to Salisbury (SBY)

8.4/10 Very good! (1,008 reviews)

The location is absolutely perfect! The hotel is a bit older but very well-maintained and in good condition. We spent three nights here and have zero complaints. Thanks for a wonderful stay!

Reviewed on Jun 21, 2026

St Michaels Inn

CA $927

per person

Aug 13 - Aug 17

found 15 hours ago

Roundtrip flight included

Toronto (YYZ) to Salisbury (SBY)

8.2/10 Very good! (1,002 reviews)

Did like convenience to Easter Shore shops and events and other islands. However, there was no view whatsoever but a dark outdoor hall, the toilet was built for a child, and the shower was tepid at best.

Reviewed on Jun 21, 2026

Commander Beach House Hotel

Downtown Ocean City

CA $807

per person

Sep 3 - Sep 7

found 18 hours ago

Roundtrip flight included

Montreal (YMQ) to Salisbury (SBY)

7/10 Good! (642 reviews)

We enjoyed our stay.

Reviewed on Jun 23, 2026

Ready to book your vacation to Chestertown?

Choose your dates

Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Fully refundable

CA $146

CA $162 total

Jul 19 - Jul 20

includes taxes & fees

8.6/10 Excellent! (926 reviews)

"Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room."

Reviewed on Jun 14, 2026

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

Fully refundableReserve now, pay when you stay

CA $102

CA $113 total

Jun 30 - Jul 1

includes taxes & fees

7.2/10 Good! (458 reviews)

"The property is a little older and could benefit from a good deep cleaning of carpets and upholstery, but the bed and bathroom were clean and the staff were great. Considering the price of other accomodations in the area it's an excellent value for the money if you're just looking for a clean place ..."

Reviewed on Jun 22, 2026

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd Chestertown MD

CA $187

CA $214 total

Jun 29 - Jun 30

includes taxes & fees

7.8/10 Good! (88 reviews)

"Old facility but everywhere clean. There have a private beach. It was so nice. So cute place but restaurants are closed weekday. Microwave and coffee are not in room.AC was noisy."

Reviewed on Jun 16, 2026

See all 1,087 properties in Chestertown

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 Chestertown

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.

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Your Chestertown Vacation

Top Chestertown Vacation Deals

Eden Roc Motel

Harrison Hall Hotel

Dunes Court

St Michaels Inn

Commander Beach House Hotel

Ready to book your vacation to Chestertown?

Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

Discover the most popular places to visit in Chestertown

Historical Society of Kent County Maryland

Wilmer Park

Explore a world of travel with Expedia

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