Chestertown Vacations

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

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    Plan, book, and manage your trip all in one place

Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ₩154,480 per night from Aug 3 to Aug 4
₩154,480
₩171,473 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (778 reviews)
"We have stayed with this Comfort Inn, Chestertown, MD location in the past. Breakfast is handy, nearby grocery store and eateries are convenient. Farmers Market on Saturday and trendy Mom & Pop shops are close by. The staff are efficient and ice machines are abundant along with a washer/dryer (coins ..."

Reviewed on Jul 5, 2025

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ₩94,065 per night from Jul 17 to Jul 18
₩94,065
₩104,412 total
Jul 17 - Jul 18
includes taxes & fees
7.2/10 Good! (370 reviews)
"Had a good time and enjoyed the quietness at the hotel."

Reviewed on Jul 3, 2025

Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
The price is ₩181,943 per night from Jul 13 to Jul 14
₩181,943
₩201,957 total
Jul 13 - Jul 14
includes taxes & fees
7.8/10 Good! (53 reviews)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"

Reviewed on Jun 22, 2025

The Lodge at Great Oak Landing
See all 1,073 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

Crumpton Auction

4.5/5(3 reviews)

Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.

Crumpton Auction

Frequently asked questions

How much does a Chestertown vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Chestertown costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chestertown?
December, January and February are great times to search for cheap Chestertown vacation packages. Opting to travel in quieter periods means you can usually find better prices on flights and hotels.
How many days is enough for Chestertown?
Generally, a handful of days is great for a Chestertown vacation. With a well-planned itinerary, you can see all the popular attractions including Rolphs Wharf Marina, as well as discover some hidden gems along the way.
Is it worth booking a vacation package to Chestertown?
Chestertown has everything you need for an awesome getaway --- festivals, history and culture are just the start. Whether you want to visit sights like River Arts Chestertown and Historical Society of Kent County Maryland, or venture off the beaten track, you'll find plenty to see and do on your Chestertown vacation.
How to find the best Chestertown package deals?
Finding a cheap Chestertown package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Chestertown package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chestertown vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can personalize your Chestertown escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chestertown?
Score incredible bargains by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Chestertown break.
How to plan a trip to Chestertown?

  1. Choose when to travel: Check your diary and pack your bags. Your favorite time of year and the available activities will also help you decide when to visit Chestertown.
  2. Plan your budget wisely: On top of the price of your accommodations, you'll need to factor in other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Chestertown.
  3. Work out your trip length: Consider how long you'd like to spend exploring Chestertown. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Chestertown vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.