Chestertown Holidays

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Chestertown Holiday

Our pick of the best Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
The price is NZ$209 per night from 30 July to 31 July
NZ$209
30 July - 31 July
includes taxes & fees
8.6/10 Excellent! (930 reviews)
"Very clean, convenient, comfortable room. Bed was a bit too firm and breakfast was meh, but otherwise happy. Very friendly staff, will stay again."

Reviewed on 5 July 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 NZ$265 per night from 13 July to 14 July
NZ$265
13 July - 14 July
includes taxes & fees
7.8/10 Good! (89 reviews)
"Is a beautiful and quiet place to relax"

Reviewed on 29 June 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 NZ$140 per night from 20 July to 21 July
NZ$140
20 July - 21 July
includes taxes & fees
7.2/10 Good! (459 reviews)
"BED BUGS!!! For real woke up 2 am, saw one crawling on the sheets near my face, thank goodness it wasnt actually crawling on me! Packed up and left. Front desk said there had been one other recent report."

Reviewed on 6 July 2026

Red Roof Inn & Suites Chestertown
See all 1,090 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.
See properties

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.

Explore a world of travel with Expedia

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