Chestertown Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

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

Top hotels in Chestertown

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 ฿3,689 per night from 10 Aug to 11 Aug
฿3,689
฿4,094 total
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very Good! (779 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 5 Jul 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 ฿2,228 per night from 23 Jul to 24 Jul
฿2,228
฿2,474 total
23 Jul - 24 Jul
includes taxes & fees
7.2/10 Good! (373 reviews)
"Pretty decent room size. AC didn't work very well, but we survived. Good experience overall."

Reviewed on 9 Jul 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 ฿4,296 per night from 17 Jul to 18 Jul
฿4,296
฿4,768 total
17 Jul - 18 Jul
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 22 Jun 2025

The Lodge at Great Oak Landing
See all 1,079 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.

Frequently asked questions

How much does a Chestertown holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Chestertown costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Chestertown?
December, January and February are great times to search for cheap Chestertown holiday 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 holiday. 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 holiday 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 holiday.
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," "Traveller 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Chestertown holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and accommodation individually. Better still, you can personalise 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 holiday 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 favourite 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 accommodation, 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 customised Chestertown holiday package.

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