Chestertown Vacation Packages 2026 from $296

Chestertown flight + hotel vacation packages

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

The Lodge at Great Oak Landing

$296

per person

Sep 24 - Sep 27

found 23 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Salisbury (SBY)

A golf course and a 24-hour gym are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A picnic area, laundry facilities, and barbecue grills are also on offer.

Boardwalk One

Downtown Ocean City

$984

per person

Sep 22 - Sep 25

found 12 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) 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.

Fenwick Shores, Tapestry Collection by Hilton

$1,195

per person

Oct 1 - Oct 8

found 1 day 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.

Americana Princess Suites and Condos

Downtown Ocean City

$1,157

per person

Sep 22 - Sep 25

found 12 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.

Ocean 1 Hotel and Suites

Downtown Ocean City

$821

per person

Sep 16 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Salisbury (SBY)

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.

Top Chestertown hotels deals

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Free Cancellation

$104 nightly

$115 total

Sep 13 - Sep 14

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.

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd Chestertown MD

Free Cancellation

$124 nightly

$137 total

Aug 16 - Aug 17

Total with taxes and fees

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

Free Cancellation

Reserve now, pay when you stay

$63 nightly

$70 total

Aug 19 - Aug 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, laundry facilities, and free newspapers are also on offer.

Historic Inns of Annapolis

58 State Circle Annapolis MD

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$143 total

Aug 27 - Aug 28

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.

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

Free Cancellation

Reserve now, pay when you stay

$207 nightly

$236 total

Aug 23 - Aug 24

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.

Pendry Baltimore

1715 Thames St. Baltimore MD

Free Cancellation

Reserve now, pay when you stay

$387 nightly

$455 total

Aug 31 - Sep 1

Total with taxes and fees

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

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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.

Stay near popular Chestertown attractions

Washington College

8.6/10 (87 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.

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Frequently asked questions

How much are vacation packages to Chestertown?

Travelocity provides package deals to Chestertown, including hotels and flights, starting from an impressive $296. 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.