Chestertown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Chestertown Vacation

There's no better way to embark on an adventure than with one of our vacation 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 Center for the Arts at the Prince Theater, 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 vacation on Expedia.

Ready to book your vacation to Chestertown?

 

Choose your dates

Chestertown Hotel Deals

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 refundable
The price is CA $151 per night from Nov 10 to Nov 11
CA $151
CA $173 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very good! (127 reviews)
"This is a marina, not really a hotel!"

Reviewed on Nov 3, 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 CA $101 per night from Nov 16 to Nov 17
CA $101
CA $112 total
Nov 16 - Nov 17
includes taxes & fees
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
The price is CA $138 per night from Dec 6 to Dec 7
CA $138
CA $153 total
Dec 6 - Dec 7
includes taxes & fees
8.6/10 Excellent! (998 reviews)
"It had a very pleasant sent in the hotel rooms and hallways"

Reviewed on Nov 4, 2026

Comfort Inn & Suites Chestertown
See all 1,102 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Chestertown attractions

Washington College

8.6/10 (87 reviews)
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
See properties

Frequently asked questions

How much does a Chestertown vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Chestertown costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chestertown?
If you're hoping to snag a cheap Chestertown vacation package, consider travelling in December, January and February. You'll typically find lower rates on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Chestertown?
You can explore all the main sights in Chestertown within a few days, including the must-see Historical Society of Kent County Maryland. If you're after a longer Chestertown vacation, look at what kind of activities and day trips are available in the area.
Is it worth booking a vacation package to Chestertown?
Well known for its festivals, history and culture, a Chestertown vacation is a hit with all kinds of travellers. Be sure to visit leading sights like River Arts Chestertown and Historical Society of Kent County Maryland, and consider renting some wheels for day trips to discover even more.
How to find the best Chestertown package deals?
Begin your search for a Chestertown package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Chestertown package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chestertown getaway off to a flying start.
Is it cheaper to book a Chestertown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights separately. Better still, you can tailor your Chestertown escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chestertown?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Chestertown getaway.
How to plan a trip to Chestertown?

  1. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the activities on offer will also help you decide when to vacation in Chestertown.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Chestertown.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Chestertown. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the perfect Chestertown vacation package for you.

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