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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.
Park Place Hotel

Park Place Hotel

3 out of 5
Price was $206, price is now $193 per person
$193
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star beach hotel in Ocean City. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
Price was $361, price is now $294 per person
$294
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
Price was $1,323, price is now $1,128 per person
$1,128
per person
Nov 22 - Nov 28
found 14 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3.5-star apartment in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Maryland Beach are located nearby.
Boardwalk One

Boardwalk One

3 out of 5
Price was $999, price is now $889 per person
$889
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star beach aparthotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Price was $629, price is now $573 per person
$573
per person
Nov 21 - Nov 23
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star 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 Boardwalk and Bethany Beach Bandstand are located nearby.
Beach Walk

Beach Walk

2 out of 5
Price was $3,985, price is now $3,683 per person
$3,683
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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.
Shore Point Cottages

Shore Point Cottages

3 out of 5
Price was $255, price is now $236 per person
$236
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star cottage in Berlin. 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.
Cypress River Inn & Spa

Cypress River Inn & Spa

5 out of 5
Price was $1,227, price is now $1,156 per person
$1,156
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Stay at this 5-star luxury B&B in Snow Hill. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Worcester County Library Snow Hill Branch and Bishop's Stock Fine Art, Craft & Wine are located nearby.

Chestertown Vacation Packages 3-4 Night Stays

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 $750, price is now $703 per person
$703
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Wingate by Wyndham Salisbury

Wingate by Wyndham Salisbury

2.5 out of 5
Price was $847, price is now $786 per person
$786
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop 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 $845, price is now $785 per person
$785
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $771, price is now $719 per person
$719
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $999, price is now $889 per person
$889
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
North Ocean City
Price was $1,323, price is now $1,128 per person
$1,128
per person
Nov 22 - Nov 28
found 14 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Price was $1,336, price is now $1,159 per person
$1,159
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Wingate by Wyndham Salisbury

Wingate by Wyndham Salisbury

2.5 out of 5
Price was $1,065, price is now $978 per person
$978
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop 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.

Spirit Airlines
Tue, Jan 13 - Wed, Jan 21
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 2 days ago
$60
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jan 21, priced at $60 found 2 days ago
Spirit Airlines
Thu, Nov 13 - Wed, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 2 hours ago
$60
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Nov 19, priced at $60 found 2 hours ago
Frontier Airlines
Fri, Nov 14 - Sat, Nov 15
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 15, priced at $70 found 1 day ago
Spirit Airlines
Tue, Nov 4 - Tue, Nov 4
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Nov 4 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Nov 4, priced at $74 found 1 day ago