Chestertown Vacations from $663

A Chestertown vacation package lets you combine round-trip flights, hotel stays, and a rental car. Many hotels available in packages offer ocean views, with about half of package hotels featuring this amenity, enhancing your coastal experience. Flights typically arrive at Philadelphia International Airport (PHL).


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

When you bundle, you can save up to 30%*. To save money on a Chestertown package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

For families, a Chestertown vacation package with a stay at The Lodge at Great Oak Landing is a strong choice. This 3.5-star property, located about 8 miles from central Chestertown, offers family rooms, an outdoor pool, and a playground, making it ideal for younger guests. Travelers frequently praise the helpful staff and excellent food, noting the overall absolutely beautiful setting and excellent location.


Travelers seeking the best vacation packages in Chestertown for value might consider a package including Comfort Inn & Suites Chestertown. Rated 8.2 out of 10, this hotel is about a 15-minute walk from central Chestertown and provides newly renovated rooms, free breakfast, and an outdoor pool. Guests often highlight the good value and nice staff.

Chestertown is primarily a beach destination, offering a relaxed coastal experience for your Chestertown vacation. About half of package hotels offer ocean views, and you can enjoy the sand and water at Betterton Beach, located about 4 miles from central Chestertown.


However, Chestertown also has a rich cultural and historical side. The town was founded in 1706 and served as one of Maryland's Royal Ports of Entry, leading to many historic homes. You can explore the Chestertown Historic District, about a 10-minute walk from the center, and learn about its past, including the legendary Chestertown Tea Party Festival.

A Chestertown vacation offers a blend of outdoor activities and historical exploration:


Browse and book things to do in Chestertown on Expedia.

For a Chestertown vacation package, a rental car offers the most flexibility, especially if you plan to explore beyond the immediate downtown area. Maryland Route 213 is a significant highway for navigating the region. While downtown Chestertown is very walkable, with shops and historic houses easily accessible on foot, many attractions and beaches are spread out.


If your Chestertown beach vacation packages focus on a specific resort, you might not need a car for daily activities, but for wider exploration or reaching airports like Philadelphia International Airport (PHL), Ronald Reagan Washington National Airport (DCA), Washington Dulles International Airport (IAD), Baltimore Washington International Thurgood Marshall Airport (BWI), or Harrisburg International Airport (MDT), a car is highly recommended.

Chestertown vacation package hotels offer a range of locations, from the heart of town to more secluded spots. For instance, Comfort Inn & Suites Chestertown, rated 8.2 out of 10, is conveniently located about a 15-minute walk from central Chestertown, and travelers often note its good value and easy overall experience.


If you prefer a stay further out, the 3.5-star The Lodge at Great Oak Landing is about 8 miles from central Chestertown, with guests praising its excellent location and comfortable rooms. Hotels closer to the center provide easy access to downtown attractions, while those further out offer a more tranquil setting, often closer to natural areas.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chestertown vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Chestertown, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Chestertown vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chestertown getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.