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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    Save up to £335 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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    Rest easy

    Packages with flights are ATOL protected

Your Chestertown Holiday

There's no better way to embark on an adventure than with one of our holiday packages to Chestertown. The colonial history and cultural experiences are just two of the countless reasons to spend some time in this captivating city. Fill your free time with visits to Washington College, Rolphs Wharf Marina and Garfield Centre for the Arts at the Prince Theatre, some of the things you simply have to see during a trip to Chestertown. A couple of quick clicks is all it takes to put together a tailor-made Chestertown holiday on Expedia.

Chestertown Essential Information

Language
English
Currency
U.S dollars
Population
5,100
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Historical Society of Kent County Maryland, Garfield Centre for the Arts at the Prince Theatre and Crow Farm and Vineyard

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 £91 per night from 7 Sept to 8 Sept
£91
7 Sept - 8 Sept
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 £59 per night from 17 Aug to 18 Aug
£59
17 Aug - 18 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 £109 per night from 12 Aug to 13 Aug
£109
12 Aug - 13 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chestertown travel package cost?
From as low as . Yes, you read that right. Our Chestertown travel packages are the quickest way to make your dollars go much further. Bundle your hotels, flights and rental car and get out and explore this fabulous destination.
If I'm not able to travel, can I cancel my Chestertown travel package?
You sure can, and we're here to help. You may be able to cancel or change your Chestertown travel package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, take a look at our Customer Service Portal for more information.
How do I get a cheap travel package to Chestertown?
Simply by bundling. Flights, rental cars and hotels — combine whatever you need into a Chestertown travel package to save a pile of cash. Score even more deals when you add extras such as day tours to your booking. But that's not the only impressive part. You have the flexibility to customize your holiday your way. We offer over 550 partner airlines and 1,000,000 hotels throughout the world, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Chestertown holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply pick the payment plan that works for you during the checkout process and take away the stress of budgeting for your next trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your holiday buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all budgets, so you can have that well-deserved holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan from Klarna.

Where should I stay in Chestertown?
With loads to explore in Chestertown, it's a good idea to lock in a hotel near its attractions. Washington College, Historical Society of Kent County Maryland and Rolphs Wharf Marina are some good ones to add to your to-do list.
What are the top hotels in Chestertown?
If it's your first time in Chestertown, lock in a room at Comfort Inn & Suites Chestertown or Red Roof Inn & Suites Chestertown. Both hotels offer comfortable beds and are popular options with many travellers.
How far in advance should I book my Chestertown holiday?
Reserving your seat early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, last-minute deals to Chestertown are still known to appear just a few weeks before departure.
What does an Expedia Chestertown travel package include?
Select from any combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your airfare class? That's also easy to do. The choice is all yours when it comes to crafting your perfect Chestertown escape.
What should I know before booking a Chestertown travel package?
You'll pick up amazing savings when you combine your hotels, flights and rental cars into a travel package. Not just that, booking everything in one place simply makes planning easier. So why waste your time or money? Whether you're putting together a luxury romantic escape or a low-cost family break, have a look at our travel packages today.
Can I choose my airline with a Chestertown Expedia travel package?
Expedia has access to more than 550 partner airlines globally, so you sure can! Just select the airline you want and put together your ideal Chestertown getaway.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.