Chestertown Vacations

Book a Hotel + Flight together to unlock savings

Photo by Patricia Knorr
  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

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 AED 448 per night from Jun 5 to Jun 6
AED 448
AED 497 total
includes taxes & fees
5 Jun - 6 Jun
8.4/10 Very Good! (766 reviews)
"Better than I expected"

Reviewed on 26 May 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 AED 251 per night from Jun 10 to Jun 11
AED 251
AED 279 total
includes taxes & fees
10 Jun - 11 Jun
7.2/10 Good! (360 reviews)
"Was a decent place to stay for the price."

Reviewed on 29 May 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 refundable
The price is AED 486 per night from Jun 15 to Jun 16
AED 486
AED 539 total
includes taxes & fees
15 Jun - 16 Jun
7.6/10 Good! (48 reviews)
"Wonderful quiet place. Enjoyed our night."

Reviewed on 27 April 2025

The Lodge at Great Oak Landing
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 vacation package cost?
Offering excellent value package deals on Expedia, you’ll be thrilled with how little a vacation to Chestertown costs! Expedia’s packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chestertown?
December, January and February are great times to search for cheap Chestertown vacation packages. Opting to travel in quieter periods means you can usually find better prices on flights and hotels.
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,” “Traveler 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chestertown vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can personalize 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 vacation 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 favorite 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 accommodations, 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 customized Chestertown vacation package.

Discover the most popular places to visit in Chestertown