Chestertown Holidays

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Your Chestertown Holiday

There's no better way to escape than with one of our holiday packages to Chestertown. The colonial history and cultural experiences are just a couple of the convincing reasons to visit this awesome city. If your trip to Chestertown includes some sightseeing, visit renowned attractions like Washington College, Rolphs Wharf Marina and River Arts Chestertown. Whoever you're heading away with and whatever your bank balance, your ultimate Chestertown holiday is just clicks away with 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

Our pick of the best Chestertown Hotel Deals

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking and a 24-hour front desk. Discover genuine guest reviews for Red Roof Inn & Suites Chestertown ...
7.4/10 Good! (251 reviews)
"Need to pick up the grounds but overall satisfied"

Reviewed on 29 Feb 2024

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (658 reviews)
"Great"

Reviewed on 25 Mar 2024

Comfort Inn & Suites Chestertown
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Stay at this historic hotel in Annapolis. Enjoy free WiFi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,610 reviews)
A wonderful stay in every way
"Easy quick check in. The Inn is very unique and makes for a lovely stay. Very close to restaurants, shops and water attractions. The room was very clean and comfortable with everything necessary for a night away. We’ll definitely be back."

Reviewed on 25 Mar 2024

Historic Inns of Annapolis
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 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.

Discover the most popular places to visit in Chestertown

* 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.