Deals on vacations and trips to Chestertown

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Dunes Suites Oceanfront

Dunes Suites Oceanfront

2.5 out of 5
Midtown Ocean City
Price was $545, price is now $479 per person
$479
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) to Salisbury (SBY)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Price was $755, price is now $639 per person
$639
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) to Salisbury (SBY)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $617, price is now $552 per person
$552
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) 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.
Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

3 out of 5
North Ocean City
Price was $606, price is now $552 per person
$552
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) 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.
Hotel Bethany Beach

Hotel Bethany Beach

2.5 out of 5
Price was $572, price is now $521 per person
$521
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) to Salisbury (SBY)
This hotel features an outdoor pool and a gym. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Self parking, a business center, and a snack bar/deli are also offered.

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
$100 nightly
The price is $111 total per night
$111 total
Feb 24 - Feb 25
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
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown MD
Get rates
This cabin features a garden, laundry facilities, and barbecue grills.
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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

3 out of 5
4 Philadelphia Ct Rosedale MD
Free Cancellation
Reserve now, pay when you stay
$64 nightly
The price is $74 total per night
$74 total
Feb 17 - Feb 18
Total with taxes and fees
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.
Breakfast included
Pet friendly
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
$419 nightly
The price is $492 total per night
$492 total
Mar 12 - Mar 13
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

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
$92 nightly
The price is $108 total per night
$108 total
Feb 22 - Feb 23
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
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $106 total per night
$106 total
Feb 23 - Feb 24
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
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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

Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.

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.

Washington College

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.

Historical Society of Kent County Maryland

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

Frequently asked questions

How much are vacation packages to Chestertown?
Travelocity provides package deals to Chestertown, including hotels and flights, starting from an impressive $479. 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.

Photos of local treasures

Browse Chestertown vacation photos for more inspiration

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA
Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.
Eastern Shore small towns in Maryland, USA. Traveling the Eastern Shore points o f Maryland this weekend, we came across this local church with gravestones. We found several of these local churches along with the many farms and inlets leading to the Chesapeake bay.

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