Chestertown Vacation Packages 2026 from $820

Chestertown flight + hotel vacation packages

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

Courtyard by Marriott Salisbury

$820

per person

Jul 17 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$1,429

per person

Jul 27 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Syracuse (SYR) to Salisbury (SBY)

This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.

Cypress River Inn & Spa

$945

per person

Jul 17 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

A restaurant, free self parking, and a garden are among this bed & breakfast's amenities. WiFi in public areas is free. A snack bar/deli, a communal living room, and a picnic area are also on offer.

Ocean 1 Hotel and Suites

Downtown Ocean City

$1,259

per person

Jul 27 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Syracuse (SYR) 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.

Ocean Terrace Family Apartments

Downtown Ocean City

$1,295

per person

Jul 27 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Syracuse (SYR) 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

$108 nightly

$120 total

Jun 14 - Jun 15

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

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$80 total

May 20 - May 21

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.

Pet friendly

Parking included

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd Chestertown MD

Free Cancellation

$136 nightly

$151 total

May 17 - May 18

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

$159 nightly

$182 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 31 - Jun 1

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

Don't see what you're looking for?

See all available properties in Chestertown

View all properties

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.

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.

Frequently asked questions

How much are vacation packages to Chestertown?

Travelocity provides package deals to Chestertown, including hotels and flights, starting from an impressive $820. 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.