Deals on vacations and trips to Chestertown

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Chestertown flight + hotel vacation packages

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
per person
Jul 7 - Jul 11
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
This hotel features a restaurant and 2 bars/lounges. Enjoy the indoor pool and perks like free self parking and free WiFi. A safe deposit box is provided and the front desk is staffed around-the-clock.
Flamingo Motel

Flamingo Motel

2 out of 5
Midtown Ocean City
per person
Jul 7 - Jul 11
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
This motel features an outdoor pool and an indoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace is provided and the front desk is staffed around-the-clock.
Paradise Plaza Inn

Paradise Plaza Inn

3 out of 5
Downtown Ocean City
per person
Jul 7 - Jul 11
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
A seasonal outdoor pool is featured at this hotel, along with free WiFi in public areas and laundry facilities. Traveling on business? Take advantage of the business center and onsite conference space. The front desk is staffed around-the-clock and concierge services are on offer.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
per person
Jul 7 - Jul 11
Roundtrip non-stop flight included
Detroit (DTW) 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.
Majestic Hotel & Apartments

Majestic Hotel & Apartments

3 out of 5
Downtown Ocean City
per person
Jul 7 - Jul 11
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A grocery/convenience store, a picnic area, and concierge services are also on offer.
Prices and availability subject to change. Additional terms may apply.

Top Chestertown hotels deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
Free Cancellation
Reserve now, pay when you stay
The price is $110 per night
$110
per night
Apr 30 - May 1
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.
Pet friendly
Breakfast included
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Free Cancellation
Reserve now, pay when you stay
The price is $85 per night
$85
per night
Apr 21 - Apr 22
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
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street, Baltimore, MD
Free Cancellation
Reserve now, pay when you stay
The price is $107 per night
$107
per night
May 5 - May 6
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.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $145 per night
$145
per night
May 13 - May 14
This hotel features a restaurant, 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
Parking available
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

2.5 out of 5
4 Philadelphia Ct, Rosedale, MD
Free Cancellation
Reserve now, pay when you stay
The price is $80 per night
$80
per night
May 1 - May 2
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
Free Cancellation
Reserve now, pay when you stay
The price is $384 per night
$384
per night
May 9 - May 10
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and visit the 2 bars/lounges and poolside bar for drinks.
Pet friendly
Breakfast available
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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

Image for Washington College

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.

Washington College
Image for Rolphs Wharf Marina

Rolphs Wharf Marina

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

Rolphs Wharf Marina
Image for River Arts Chestertown

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

Frequently asked questions

How much are vacation packages to Chestertown?
Travelocity provides package deals to Chestertown, including hotels and flights, starting from an impressive $662. 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.