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Chestertown Vacation Packages

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Chestertown Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD

2 out of 5
Price was $620, price is now $582 per person
$582
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds are located nearby.
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3 out of 5
Price was $762, price is now $702 per person
$702
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Best Western Salisbury Plaza

Best Western Salisbury Plaza

2.5 out of 5
Price was $710, price is now $659 per person
$659
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Poplar Hill Mansion and Coco's Funhouse are located nearby.
Baymont By Wyndham Salisbury Md

Baymont By Wyndham Salisbury Md

2.5 out of 5
Price was $1,071, price is now $995 per person
$995
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this hotel in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Regal Salisbury and Centre at Salisbury are located nearby.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Price was $746, price is now $694 per person
$694
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the pool and the restaurant in our reviews. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $631, price is now $591 per person
$591
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this motel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds are located nearby.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,029, price is now $966 per person
$966
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 4-star 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.
Residence Inn by Marriott Salisbury

Residence Inn by Marriott Salisbury

3 out of 5
Price was $1,202, price is now $1,130 per person
$1,130
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star business-friendly hotel in Salisbury. Enjoy free breakfast, free parking, and an outdoor pool. Popular attractions Regal Salisbury and Centre at Salisbury are located nearby.

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $631, price is now $591 per person
$591
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3 out of 5
Midtown Ocean City
Price was $762, price is now $702 per person
$702
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Best Western Salisbury Plaza

Best Western Salisbury Plaza

2.5 out of 5
Price was $710, price is now $659 per person
$659
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $746, price is now $694 per person
$694
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $934, price is now $869 per person
$869
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,382, price is now $1,192 per person
$1,192
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Baymont By Wyndham Salisbury Md

Baymont By Wyndham Salisbury Md

2.5 out of 5
Price was $1,071, price is now $995 per person
$995
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3 out of 5
Midtown Ocean City
Price was $1,008, price is now $939 per person
$939
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Wed, Dec 17 - Thu, Dec 18
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$48 Roundtrip, found 14 hours ago
$48
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Wed, Dec 17 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Dec 18, priced at $48 found 14 hours ago
Frontier Airlines
Sat, Nov 22 - Mon, Dec 1
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$59 Roundtrip, found 2 days ago
$59
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Nov 22 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Dec 1, priced at $59 found 2 days ago
Frontier Airlines
Thu, Dec 11 - Tue, Dec 16
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$62 Roundtrip, found 2 days ago
$62
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Dec 11 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 16, priced at $62 found 2 days ago
Frontier Airlines
Fri, Jan 16 - Fri, Jan 23
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Jan 23, priced at $68 found 1 day ago