Chestertown Vacations

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Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
NT$2,294
NT$2,546 total
Oct 11 - Oct 12
includes taxes & fees
7.2/10 Good! (506 reviews)
"Not well maintained. Not welcoming. Numerous signs everywhere about what not to do, and the penalties if you do. Ice machine and vending closed on my floor. Pool closed for maintenance. Basically run down building and rooms. At least it was not noisy at night and i was able to sleep."

Reviewed on 2026/10/4

Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd Chestertown MD
Fully refundable
NT$3,441
NT$3,934 total
Oct 7 - Oct 8
includes taxes & fees
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD
Fully refundable
NT$3,195
NT$3,546 total
Nov 1 - Nov 2
includes taxes & fees
Comfort Inn & Suites Chestertown
See all 1,099 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.

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.
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River Arts Chestertown

7.4/10 (6 reviews)
Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.
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Chestertown Historic District

This preserved colonial port town showcases America's maritime heritage through 18th-century architecture. Stroll brick sidewalks along the Chester River or visit during the annual Tea Party Festival reenactments.
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Historical Society of Kent County Maryland

7.4/10 (6 reviews)
Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
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Wilmer Park

8.2/10 (13 reviews)
Nestled along the Chester River, Wilmer Park offers serene waterfront views and a modern playground for families. Bring a picnic to enjoy in the green spaces or time your visit for one of the community concerts.
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Kings Town Park

Kings Town Park offers serene pathways winding through lush greenery in Chestertown, Maryland. Enjoy morning strolls or invigorating runs along the scenic trails away from urban bustle.
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Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)
This historic 1928 theater offers an intimate setting for plays, music, and lectures in downtown Chestertown. Catch a performance during the Jazz Festival or Short Attention Span Theatre for a memorable evening.
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Crumpton Auction

8.8/10 (3 reviews)
Dixon's Auction at Crumpton showcases thousands of antiques, collectibles, and furniture in weekly discovery auctions. Arrive early to preview treasures and secure a bidder number before the fast-paced action begins.
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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 many days is enough for Chestertown?
Generally, a handful of days is great for a Chestertown vacation. With a well-planned itinerary, you can see all the popular attractions including Rolphs Wharf Marina, 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 an awesome getaway — festivals, history and culture are just the start. Whether you want to visit sights like River Arts Chestertown and Historical Society of Kent County Maryland, or venture off the beaten track, you'll find plenty to see and do 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.
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.

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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.