Chestertown Vacation Packages 2025 from $811

Chestertown flight + hotel vacation packages

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

Beach Walk

Downtown Ocean City

per person

Jul 26 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Salisbury (SBY)

This hotel features free self parking and express check-in. Express check-out is also provided.

Monte Carlo Boardwalk Oceanfront Ocean City

Downtown Ocean City

per person

Jul 26 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Salisbury (SBY)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

per person

Jul 26 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) 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 self parking and free WiFi.

The Americana Hotel

Downtown Ocean City

per person

Jul 26 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Salisbury (SBY)

This hotel features a restaurant and 2 bars/lounges. Enjoy the indoor pool and perks like free WiFi. Self parking and a safe deposit box are also offered on site.

Americana Motor Inn

Downtown Ocean City

per person

Jul 26 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) 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.

Top Chestertown hotels deals

Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD

Free Cancellation

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This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Breakfast included

Pet friendly

Red Roof Inn & Suites Chestertown

160 Scheeler Rd, Chestertown, MD

Free Cancellation

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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.

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd, Chestertown, MD

Free Cancellation

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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

Historic Inns of Annapolis

58 State Circle, Annapolis, MD

Free Cancellation

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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

Sagamore Pendry Baltimore

1715 Thames St., Baltimore, MD

Free Cancellation

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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.

Pool

Spa

Hilton Garden Inn Baltimore/White Marsh

5015 Campbell Boulevard, Baltimore, MD

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the mini golf and barbecue grills. Enjoy the 24-hour gym and perks like free self parking and free WiFi.

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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.

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 $811. 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.