Chestertown Vacation Packages 2026 from $756

Chestertown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Surf Shanty Motel

Save 100% on your flight

$756

per person

Jul 4 - Jul 8

found 15 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

This motel features 20 beach bars and express check-out. Take advantage of the free self parking.

Fenwick Shores, Tapestry Collection by Hilton

Save 100% on your flight

$1,226

per person

Jul 4 - Jul 8

found 15 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Boardwalk One

Downtown Ocean City

$1,251

per person

Jul 19 - Jul 23

found 5 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.

Americana Motor Inn

Downtown Ocean City

$1,125

per person

Jul 19 - Jul 23

found 5 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

A restaurant, free self parking, and a 24-hour front desk are among this hotel's amenities. WiFi in public areas is free. Free newspapers are provided for your convenience.

Ocean Terrace Family Apartments

Downtown Ocean City

$1,179

per person

Jul 19 - Jul 23

found 5 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.

Top Chestertown hotels deals

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Free Cancellation

$111 nightly

$123 total

May 3 - May 4

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd Chestertown MD

Free Cancellation

$110 nightly

$122 total

Apr 30 - May 1

Total with taxes and fees

A golf course, a 24-hour gym, and a restaurant are all featured at this smoke-free lodge. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a picnic area and laundry facilities.

Pool

Parking included

Blue Heron Farm Waterfront Chalet

Chestertown MD

Get rates

This farm stay features a garden, laundry facilities, and barbecue grills.

Air conditioning

Parking available

Historic Inns of Annapolis

58 State Circle Annapolis MD

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$215 total

May 25 - May 26

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.

Pet friendly

Free WiFi

Hampton Inn Baltimore/Glen Burnie

6617 Ritchie Hwy Glen Burnie MD

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$107 total

May 3 - May 4

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's dry cleaning and multilingual staff can provide around-the-clock assistance.

Breakfast included

Pet friendly

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

4 Philadelphia Ct Rosedale MD

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$85 total

May 4 - May 5

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

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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.

Popular places to visit

Washington College

4/5(13 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.

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

Garfield Center for the Arts at the Prince Theater

You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Frequently asked questions

How much are vacation packages to Chestertown?

Travelocity provides package deals to Chestertown, including hotels and flights, starting from an impressive $756. With the cash you save, you could purchase some cool tours or perhaps even add on a few extra nights to your exciting getaway.

How long should my Chestertown vacation be?

Your Chestertown trip can be as short or as long as you want, but most people stay around 2 nights. Like to hop off the beaten path and discover some less touristy sights? Book a few extra nights and experience another side of this place.

Where can I get the best vacation package deals for Chestertown?

There are incredible Chestertown package deals to be scored with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties all over the world? Remember this when you're ready to tick another destination off your must-visit list.

Why should I book my Chestertown vacation bundle via Travelocity?

Whether you're in search of the ultimate unplugged getaway or after the fun and excitement of the big smoke, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of different websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available for you round-the-clock.

Will I save money on my Chestertown car rental if I combine it with my hotel or flight?

With a Chestertown vacation package, you can bundle your hotel, car and flight bookings and save loads. When you're ready to discover the best of this exciting location, why not check out White House? This famous attraction is 55 mi from Chestertown. With your own rental car, you'll be there in a jiffy.

What is the best time of year to go to Chestertown?

You'll pick up the cheapest hotel prices in and pay the highest prices during . You can usually expect it to be less busy in May, November and December, while you'll find more fellow travelers to meet during the months of February, March and October. It all comes down to what prices you're willing to pay, the weather and how well you handle crowds.

Which airport is best for Chestertown?

Ronald Reagan Washington National Airport (DCA), 60 mi southwest of the city center, is where many visitors start their adventures in Chestertown. That said, Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (30 mi away from central Chestertown) could be more convenient for you.

What is there to do in Chestertown?

While venturing off the beaten track can be rewarding, you shouldn't ignore the popular attractions that make a place famous. Washington College and River Arts Chestertown are a couple of them in Chestertown.

Where should I stay when visiting Chestertown?

If you're after somewhere to lay your head, take a look at the Comfort Inn & Suites Chestertown. It's the top choice for many travelers.