Chestertown Vacation Packages 2025/2026 from $235

Chestertown flight + hotel vacation packages

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

Holiday Inn Ocean City by IHG

North Ocean City

$235

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

New York (LGA) to Salisbury (SBY)

This smoke-free hotel features 2 restaurants, 2 hot tubs, and an indoor pool. Families will appreciate the arcade/game room, kid-friendly dining, and free supervised childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Ashore Resort & Beach Club

North Ocean City

$335

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

New York (LGA) to Salisbury (SBY)

This traditional hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at the beach bar and enjoy perks like free self parking and free WiFi.

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$339

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

New York (LGA) 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.

Princess Royale Oceanfront Resort

North Ocean City

$276

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

New York (LGA) to Salisbury (SBY)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Dine at the beachfront restaurant and relax with beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with volleyball.

Holiday Inn & Suites Ocean City by IHG

Downtown Ocean City

$319

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

New York (LGA) to Salisbury (SBY)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the hot tub, poolside bar, and laundry facilities.

Top Chestertown hotels deals

Red Roof Inn & Suites Chestertown

160 Scheeler Rd, Chestertown, MD

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$85 total

Sep 14 - Sep 15

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

Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$122 total

Sep 14 - Sep 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

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd, Chestertown, MD

Free Cancellation

$147 nightly

$163 total

Sep 9 - Sep 10

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

Historic Inns of Annapolis

58 State Circle, Annapolis, MD

$158 nightly

$181 total

Sep 14 - Sep 15

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

Sagamore Pendry Baltimore

1715 Thames St., Baltimore, MD

$392 nightly

$461 total

Sep 28 - Sep 29

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

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street, Baltimore, MD

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$125 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel features a restaurant, an indoor 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 free perks like buffet breakfast and free self parking.

Pool

Hot Tub

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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

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.

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. 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 $235. 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.