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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
Price was $270, price is now $235 per person
$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
Price was $428, price is now $335 per person
$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
Price was $416, price is now $339 per person
$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
Price was $335, price is now $276 per person
$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
Price was $384, price is now $319 per person
$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
The price is $85 total per night
$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
The price is $122 total per night
$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
The price is $163 total per night
$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
The price is $181 total per night
$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
The price is $461 total per night
$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
The price is $125 total per night
$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
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.
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