Chestertown Vacations from $643

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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.

The Latest Chestertown vacation packages

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Lewes Rehoboth Beach

Home2 Suites by Hilton Lewes Rehoboth Beach

3 out of 5
Price was $766, price is now $643 per person
$643
per person
Sep 17 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
9.4/10 Exceptional! (1,007 reviews)
We had a nice clean room with great breakfasts and nice staff

Reviewed on Aug 5, 2026

White Marlin Inn

White Marlin Inn

2.5 out of 5
Downtown Ocean City
Price was $1,539, price is now $1,014 per person
$1,014
per person
Sep 8 - Sep 11
found 10 hours ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
5.4/10 (45 reviews)
This was the most disgusting property I’ve ever stayed in. We were appalled and had to have our room changed . We found used femine hygiene products on the floor in the bathroom. We never received clean towels or had the garbage changed.

Reviewed on Aug 4, 2026

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was $1,702, price is now $1,232 per person
$1,232
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
6.6/10 (39 reviews)

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was $1,057, price is now $867 per person
$867
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
7.8/10 Good! (42 reviews)
Both my wife and I are in our mid seventies. Our unit was on the 3rd floor with no elevator. As soon as you enter the building you are hit with a musty smell and a damp, clammy sense. Same thing in the unit itself. One dining room chair was broken. The vent over one of the beds hung down a few inches precariously held up by tape. The door to the balcony patio had a one inch gap to the threshold. Hot water for showers was lukewarm at best. Some ants and flies.

Reviewed on Aug 5, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,024, price is now $853 per person
$853
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
9.4/10 Exceptional! (805 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Chestertown
View all trips

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

Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
$107 nightly
The price is $119 total per night from Aug 26 to Aug 27
$119 total
Aug 26 - Aug 27
Total with taxes and fees
8.6/10 Excellent! (943 reviews)
"We got a free upgrade just by asking!"

Reviewed on Jul 31, 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
$124 nightly
The price is $137 total per night from Aug 6 to Aug 7
$137 total
Aug 6 - Aug 7
Total with taxes and fees
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
$63 nightly
The price is $70 total per night from Aug 12 to Aug 13
$70 total
Aug 12 - Aug 13
Total with taxes and fees
7.2/10 Good! (474 reviews)
"Nice clean friendly staff"

Reviewed on Aug 5, 2026

Red Roof Inn & Suites Chestertown
See all 1,091 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.

Find the Best Chestertown Vacation Packages

Chestertown Essential Information

Language
English
Currency
U.S dollars
Population
5,100
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Waterman’s Museum, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chestertown vacation package cost?
Offering excellent value package deals from $643 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?
May, November and December are great times to search for cheap Chestertown vacation packages. Choosing to travel in less busy months means you can generally find better prices on flights and hotels.
How many days is enough for Chestertown?
Generally, a few days is ideal for a Chestertown vacation. With a well-organized schedule, you can check out all the main attractions like Washington College, as well as discover some hidden gems along the way.
Is it worth booking a vacation package to Chestertown?
Chestertown has everything you need for a memorable trip — festivals, history and culture are just the start. Whether you'd like to visit sights such as River Arts Chestertown and Historical Society of Kent County Maryland, or take the path less traveled, you'll have plenty to explore on your Chestertown vacation.
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.
Does Expedia offer Book Now, Pay Later Chestertown vacation packages?
Jet off on your dream escape to Chestertown with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up bargains before they disappear.

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.