Chestertown Vacations from $397

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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.
St Michaels Inn

St Michaels Inn

2.5 out of 5
Price was $487, price is now $397 per person
$397
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8.2/10 Very Good! (1,003 reviews)
Room was fine. Breakfast was poor with two empty hot breakfast servers. Rest of food substandard. Staff was nice

Reviewed on Jan 18, 2026

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
Downtown St. Michaels
Save 100% on your flight
Price was $1,710, price is now $1,156 per person
$1,156
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.6/10 Exceptional! (369 reviews)
Friendly and attentive staff, good cleaning services

Reviewed on Oct 26, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,694, price is now $2,161 per person
$2,161
per person
Apr 1 - Apr 5
just found
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
7.6/10 Good! (95 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing

Reviewed on Oct 17, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,318, price is now $1,076 per person
$1,076
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was $822, price is now $683 per person
$683
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
6/10 (681 reviews)
Very helpful staff and clean property

Reviewed on Dec 2, 2025

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Discover the most popular places to visit in Chestertown

Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.

Washington College

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.

Washington College

Historical Society of Kent County Maryland

You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Historical Society of Kent County Maryland

Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

Wilmer Park

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
$101 nightly
The price is $112 total per night from Mar 8 to Mar 9
$112 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (879 reviews)
I reserved a suite for two nights on 12/26/25. Almost 2 months in advance. When I arrived the check-in girl said that she downgraded my room to a double because they were overbooked and since I only two people in my group she gave my suite to a party with 4 people because they needed more room than ...

Reviewed on Feb 17, 2026

Comfort Inn & Suites Chestertown
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $82 total per night from Mar 1 to Mar 2
$82 total
Mar 1 - Mar 2
Total with taxes and fees
7/10 Good! (1,171 reviews)
This was a run down, smelly property with questionable people staying at the same time. The main issues: - The room, which was supposed to be nonsmoking, reeked of cigarettes and was almost impossible to sleep in - The bathroom door was dirty, covered with red stains - The sink was cracked - The ...

Reviewed on Feb 25, 2026

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $237 total per night from Mar 6 to Mar 7
$237 total
Mar 6 - Mar 7
Total with taxes and fees
9/10 Wonderful! (1,890 reviews)
The room really showed its age. The entire room was tilted.... so much so that a bottle rolled on the floor from the left to the right without any push. The bed was likewise tilted and really difficult to sleep comfortably. The elevator was out of order, and there were older guests on the 3rd floor ...

Reviewed on Feb 23, 2026

Historic Inns of Annapolis
See all 1,080 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

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Frequently asked questions

How much does a Chestertown vacation package cost?
Offering excellent value package deals from $397 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.

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