Chestertown Holidays

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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 refundable
The price is 2.919.334 ₫ per night from 16 Aug to 17 Aug
2.919.334 ₫
3.240.461 ₫ total
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (935 reviews)
"We stayed there two nights for my daughter’s tournament. The room is clean and quiet, the breakfast is good. Highly recommended!"

Reviewed on 16 Jul 2026

Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is 3.473.272 ₫ per night from 21 Jul to 22 Jul
3.473.272 ₫
3.970.991 ₫ total
21 Jul - 22 Jul
includes taxes & fees
8/10 Very good! (91 reviews)
"We love this place 😀….great pool nice room,free golf!!!!….in the middle of nowhere,but that’s nice…15 minutes to Chestertown…we come every year 👍"

Reviewed on 7 Jul 2026

The Lodge at Great Oak Landing
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 1.771.841 ₫ per night from 29 Jul to 30 Jul
1.771.841 ₫
1.966.743 ₫ total
29 Jul - 30 Jul
includes taxes & fees
7.2/10 Good! (462 reviews)
"Big room,very comfortable bed,direct tv….pool was out of order,apparently has been for quite a while…..enjoyed our stay😀"

Reviewed on 11 Jul 2026

Red Roof Inn & Suites Chestertown
See all 1,092 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.

Stay near popular Chestertown attractions

Washington College

8.6/10 (87 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
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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.

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