Chestertown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Patricia Knorr

  • Plan, book, travel with confidence

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    Better together

    Save up to Rp173.195 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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 Rp1.848.106 per night from 17 Aug to 18 Aug
Rp1.848.106
Rp2.051.398 total
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very Good! (791 reviews)
"Please move waffle station….it needs its own space! Could hardly get a plate and utensils with people trying to and waiting for their turn to make waffles. Breakfast choices just okay."

Reviewed on 4 Aug 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 Rp1.172.160 per night from 18 Aug to 19 Aug
Rp1.172.160
Rp1.301.097 total
18 Aug - 19 Aug
includes taxes & fees
7.2/10 Good! (384 reviews)
"Great service"

Reviewed on 1 Aug 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
Fully refundableReserve now, pay when you stay
The price is Rp2.153.844 per night from 19 Aug to 20 Aug
Rp2.153.844
Rp2.390.768 total
19 Aug - 20 Aug
includes taxes & fees
8/10 Very Good! (59 reviews)
Great staff
"Staff was very helpful in dealing with some confusion at check in. Every on went above and beyond to deal with the situation and was very welcoming during the process."

Reviewed on 28 Jul 2025

The Lodge at Great Oak Landing
See all 1,074 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.

Popular places to visit

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

Crumpton Auction

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 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.