Deals on vacations and trips to Chestertown

Save when you book Chestertown package deals

Choose two or more items and save on your trip:

Chestertown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $795, price is now $754 per person
$754
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 Shore House

The Shore House

2 out of 5
West Ocean City
Price was $2,307, price is now $1,982 per person
$1,982
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A seasonal outdoor pool and laundry facilities are also provided.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,293, price is now $2,134 per person
$2,134
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This hotel features free self parking and express check-in. Express check-out is also provided.
Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
Price was $900, price is now $852 per person
$852
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and express check-out are also offered.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,138, price is now $1,084 per person
$1,084
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

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
$103 nightly
The price is $114 total per night
$114 total
Jan 11 - Jan 12, 2026
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

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $80 total per night
$80 total
Dec 18 - Dec 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

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
$113 nightly
The price is $126 total per night
$126 total
Dec 15 - Dec 16
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

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $187 total per night
$187 total
Dec 17 - Dec 18
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.
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
$92 nightly
The price is $105 total per night
$105 total
Dec 18 - Dec 19
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

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
$375 nightly
The price is $441 total per night
$441 total
Jan 4 - Jan 5, 2026
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
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.

Washington College

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

Crumpton Auction

4.5/5(3 reviews)

Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.

Crumpton Auction

Frequently asked questions

How much are vacation packages to Chestertown?
Travelocity provides package deals to Chestertown, including hotels and flights, starting from an impressive $754. 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

Photo by Assya A
Photo by Assya A
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr

Explore More Ways to Travel with Travelocity