Chestertown Vacation Packages 2026 from $972

Chestertown flight + hotel vacation packages

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

Sahara Motel

Downtown Ocean City

$972

per person

Sep 1 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Fayetteville (XNA) to Salisbury (SBY)

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Fenwick Shores, Tapestry Collection by Hilton

$1,616

per person

Sep 1 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Fayetteville (XNA) 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.

Lankford Hotel and Lodge

Downtown Ocean City

$1,043

per person

Sep 1 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Fayetteville (XNA) to Salisbury (SBY)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A restaurant and a communal living room are also provided.

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$1,150

per person

Jul 13 - Jul 16

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) 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.

Inn at Perry Cabin

Downtown St. Michaels

Save 100% on your flight

$1,685

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip flight included

Columbus (CMH) to Salisbury (SBY)

This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room childcare. Enjoy the 3 outdoor tennis courts and perks like free valet parking and free WiFi.

Top Chestertown hotels deals

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Free Cancellation

$106 nightly

$118 total

Jul 5 - Jul 6

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

Jun 18 - Jun 19

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

$151 nightly

$168 total

Jun 15 - Jun 16

Total with taxes and fees

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.

Pool

Parking included

Historic Inns of Annapolis

58 State Circle Annapolis MD

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$166 total

Jul 1 - Jul 2

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

Jun 21 - Jun 22

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

Pendry Baltimore

1715 Thames St. Baltimore MD

Free Cancellation

Reserve now, pay when you stay

$391 nightly

$459 total

Jun 29 - Jun 30

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.

Pool

Spa

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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.

Chestertown Historic District

Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene.

Rolphs Wharf Marina

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

Frequently asked questions

How much are vacation packages to Chestertown?

Travelocity provides package deals to Chestertown, including hotels and flights, starting from an impressive $972. 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.