Search Deals onChestertown Vacation Packages
Chestertown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Red Roof Inn & Suites Chestertown
Price was $367, price is now $334 per person
$334
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.

Hyatt Regency Chesapeake Bay
Price was $1,305, price is now $1,067 per person
$1,067
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dorchester County Historical Society and Bay Country Shop are located nearby.

Strawberry Crossroads
Price was $1,050, price is now $897 per person
$897
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this cabin in Pittsville. Enjoy free parking, laundry facilities, and a picnic area.
Low expectations were not met. This property is a mess. Our 6 bunk room had 1 VERY small table and 1 indoor chair. The outdoor chairs at were dirty and falling apart. The parking area and outdoor section of our "camp site" needed mowing. Goats and chickens roam the camp sites leaving animal crap everywhere that not only gets tracked into the cabins but also attracts flies that are relentless. The cabin (#2) has a loud rattle trap of a window AC unit that is also falling apart and comes complete with a thilthy filter that looks like it has never been cleaned. Windows in the cabin had no curtains or blinds. Bathrooms are gross and the garage was overflowing. Can't say there is any indication that this property is managed by anyone who has ever stayed at a campground. The attitude of those I interacted with was indifferent to the state of the place but they were walking around barefoot (true fact). The goats are a menace and aggressive and should not be permitted to roam free. Liabilities everywhere.
Reviewed on Sep 7, 2026

Beach Walk
Price was $2,709, price is now $2,392 per person
$2,392
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Louisville (SDF) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.
Reviewed on Oct 13, 2026

Grand Hotel Ocean City Oceanfront
Price was $739, price is now $666 per person
$666
per person
Jan 15 - Jan 19
found 6 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, 4 restaurants, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Comfort Inn & Suites Chestertown
Price was $429, price is now $390 per person
$390
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.
Convenient location, friendly staff, clean
Reviewed on Nov 8, 2026

Oceanic Motel
Price was $2,765, price is now $2,513 per person
$2,513
per person
Jan 15 - Jan 19
found 6 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Salisbury (SBY)
Book a stay at this beach motel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ocean City Beach and Ocean City Boardwalk are located nearby.

Bethany Beach Ocean Suites Residence Inn by Marriott
Price was $1,014, price is now $924 per person
$924
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Bethany Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bethany Beach Bandstand and Bethany Beach Boardwalk are located nearby.
The staff was great. The breakfast is much better than other hotels with buffets. The ocean view was awesome! The room however had so little insulation at the adjoining door that conversations next door could be heard until late in the night. And voices from the next door balconies came through a vent to the outside. It would be nice if the porch lights could be turned off at some point so the dark sky could be seen. Also, it was good we could set the fan to low. We found it on high and it drowned out the ocean. The staff was very very good.
Reviewed on Nov 12, 2026
Chestertown Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Chestertown Vacation Packages 5-7 Night Stays
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Jan 12 - Wed, Jan 20
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$46 Roundtrip, found 7 hours ago
$46
Roundtrip
found 7 hours ago

Fri, Dec 4 - Wed, Dec 16
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$67 Roundtrip, found 5 hours ago
$67
Roundtrip
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Sat, Dec 5 - Mon, Dec 14
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$82 Roundtrip, found 3 hours ago
$82
Roundtrip
found 3 hours ago

Sat, Dec 12 - Sat, Dec 19
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$117 Roundtrip, found 3 hours ago
$117
Roundtrip
found 3 hours ago
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