Chestertown Vacation Packages

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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.
Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was CA $1,157, price is now CA $936 per person
CA $936
per person
May 24 - May 30
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
7.8/10 Good! (520 reviews)
I was very happy with our room - loved being on the first floor. I plan to return next time I come to the beach.

Reviewed on Oct 31, 2025

Harrison Hall Hotel

Harrison Hall Hotel

2 out of 5
Downtown Ocean City
Price was CA $1,132, price is now CA $1,008 per person
CA $1,008
per person
May 24 - May 30
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
7.4/10 Good! (1,000 reviews)
Staff was very nice and accommodating.

Reviewed on Jan 29, 2026

Bonita Beach Hotel

Bonita Beach Hotel

2 out of 5
North Ocean City
Price was CA $1,190, price is now CA $1,062 per person
CA $1,062
per person
May 24 - May 30
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
7.8/10 Good! (1,210 reviews)
Fairly clean In October fairly quiet Only issue was door to get in till we talked to the front desk. But they will be renovating & fixing door handles

Reviewed on Oct 19, 2025

Crystal Beach Hotel

Crystal Beach Hotel

2.5 out of 5
Downtown Ocean City
Price was CA $1,247, price is now CA $1,121 per person
CA $1,121
per person
May 24 - May 30
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
8.2/10 Very Good! (1,342 reviews)
Very clean, great location and great staff

Reviewed on Mar 22, 2026

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
Price was CA $1,118, price is now CA $1,015 per person
CA $1,015
per person
May 24 - May 30
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
7.2/10 Good! (429 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

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Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
The price is CA $151 per night from Apr 12 to Apr 13
CA $151
CA $168 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (890 reviews)
N/A

Reviewed on Mar 20, 2026

Comfort Inn & Suites Chestertown
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown MD
10/10 Exceptional! (16 reviews)
We brought our Lab with us. She loved looking out all the windows. She was afraid to walk up the open stairs but was content to sleep on the first floor. We enjoyed our stay at Outrange. Very quiet and secluded. Short walk to River.

Reviewed on Mar 22, 2026

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Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,873 reviews)
Clean room, friendly staff, and the PERFECT location for walking downtown Annapolis.

Reviewed on Mar 24, 2026

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Historic Inns of Annapolis
See all 1,089 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.
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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.

Historical Society of Kent County Maryland

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.

Wilmer Park

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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.