Book Exclusive Chestertown Vacation Packages
Chestertown flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG
per person
Aug. 15 - Aug. 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Harrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Delaware State Fairgrounds and Harrington Raceway and Casino are located nearby.
The Surf Shanty Motel
per person
Aug. 15 - Aug. 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Salisbury (SBY)
Stay at this motel in Dewey Beach. Enjoy free WiFi, free parking, and 20 beach bars. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach are located nearby.
Gold Leaf Hotel of Dewey - Rehoboth Beach
per person
Aug. 15 - Aug. 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Salisbury (SBY)
Book a stay at this beach hotel in Dewey Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach are located nearby.
Atlantic Oceanside Dewey
per person
Aug. 15 - Aug. 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Salisbury (SBY)
Book a stay at this beach hotel in Dewey Beach. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach are located nearby.
Home2 Suites by Hilton Lewes Rehoboth Beach
per person
Aug. 15 - Aug. 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Salisbury (SBY)
Stay at this 3-star business-friendly hotel in Lewes. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lewes Beach and Cape May - Lewes Ferry are located nearby.
Top Chestertown hotels deals
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $94 per night
CA $94
CA $104 total
includes taxes & fees
Jun 1 - Jun 2
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Pet-friendly
Parking included
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $158 per night
CA $158
CA $176 total
includes taxes & fees
Jun 15 - Jun 16
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Breakfast included
Pet-friendly
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Free cancellation
The price is CA $182 per night
CA $182
CA $202 total
includes taxes & fees
Jun 8 - Jun 9
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive are located nearby.
Pool
Parking included
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $198 per night
CA $198
CA $273 total
includes taxes & fees
Jun 1 - Jun 2
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Colonial Players and 97, 99 and 101 East Street are located nearby.
Pet-friendly
Free WiFi
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street, Baltimore, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $153 per night
CA $153
CA $179 total
includes taxes & fees
Jun 1 - Jun 2
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Baltimore Cruise Terminal and Baltimore Inner Harbor Marina are located nearby.
Pool
Hot tub
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct, Rosedale, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $109 per night
CA $109
CA $126 total
includes taxes & fees
May 27 - May 28
Book a stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions White Marsh Mall and Essex Marina are located nearby.
Breakfast included
Pet-friendly
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.
Popular places to visit
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.
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.
Chestertown Vacations
You don't need to know everything about the place to have an awesome time in Chestertown, but you will need to know a few basic things before you set off.
To help get you oriented, Chestertown sits 30 miles (48 kilometers) east of the well-known city of Baltimore.
This is an area of Eastern Shore that around 5,000 people call home.
Places to visit in Chestertown
Abandon your history books! Let the past jump off the page at Historical Society of Kent County Maryland. Seeking some more options? Great theater can challenge our expectations and asks us to aspire to bigger and better things. Catch a play at Garfield Center for the Arts at the Prince Theater and open your mind to some new ideas. And there's more. You don't need to be a prodigy to admire the vast halls and intriguing past of Washington College.Where do you fly into for Chestertown?
Slip on your headphones and watch one of the latest in-flight movies. Before long, you'll hit the tarmac at Baltimore Washington International Thurgood Marshall Airport (BWI). It's approximately 30 miles (48 kilometers) to the west from the middle of Chestertown.Photos of local treasures
Browse Chestertown vacation photos for more inspiration
