
Deals on vacations and trips to Chestertown
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Chestertown flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Princess Bayside Beach Hotel
Midtown Ocean City
per person
Aug 16 - Aug 20
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
A private beach and an outdoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Enjoy the indoor pool and perks like free self parking.

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
per person
Aug 16 - Aug 20
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.


Ashore Resort & Beach Club
North Ocean City
per person
Aug 16 - Aug 20
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.

Americana Motor Inn
Downtown Ocean City
per person
Aug 16 - Aug 20
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
A restaurant, free self parking, and a 24-hour front desk are among this hotel's amenities. WiFi in public areas is free. Free newspapers are provided for your convenience.
Top Chestertown hotels deals

Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $124 total per night
$124 total
Aug 3 - Aug 4
Total includes 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
$68 nightly
The price is $76 total per night
$76 total
Jul 14 - Jul 15
Total includes 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
$147 nightly
The price is $163 total per night
$163 total
Jul 8 - Jul 9
Total includes 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
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $163 total per night
$163 total
Jul 13 - Jul 14
Total includes 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
Free Cancellation
Reserve now, pay when you stay
$385 nightly
The price is $452 total per night
$452 total
Aug 5 - Aug 6
Total includes 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

Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy, Glen Burnie, MD
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $138 total per night
$138 total
Jul 13 - Jul 14
Total includes 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. Dry cleaning, luggage storage, and laundry facilities are also on offer.
Breakfast included
Pet friendly
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.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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.
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