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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.
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
Price was $476, price is now $428 per person
$428
per person
Feb 6 - Feb 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Salisbury (SBY)
Book a stay at this 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.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $590, price is now $487 per person
$487
per person
Feb 6 - Feb 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
The Shore House

The Shore House

2 out of 5
Price was $2,671, price is now $2,217 per person
$2,217
per person
Feb 5 - Feb 9
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Stay at this motel in Ocean City. Enjoy free breakfast, free WiFi, and free parking. 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.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Price was $1,120, price is now $981 per person
$981
per person
Feb 5 - Feb 9
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Boardwalk One

Boardwalk One

3 out of 5
Price was $733, price is now $647 per person
$647
per person
Feb 5 - Feb 9
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Book a stay at this 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.
Cambridge Inn

Cambridge Inn

2 out of 5
Price was $772, price is now $696 per person
$696
per person
Jan 25 - Jan 31
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this hotel in Cambridge. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Bay Country Shop and Dorchester County Historical Society are located nearby.
Beach Walk

Beach Walk

2 out of 5
Price was $2,674, price is now $2,414 per person
$2,414
per person
Feb 5 - Feb 9
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Holiday Inn Express Cambridge by IHG

Holiday Inn Express Cambridge by IHG

2.5 out of 5
Price was $891, price is now $827 per person
$827
per person
Jan 25 - Jan 31
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Bay Country Shop and Dorchester County Historical Society are located nearby.

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland

3 out of 5
Price was $486, price is now $416 per person
$416
per person
Feb 6 - Feb 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Salisbury (SBY)
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $590, price is now $487 per person
$487
per person
Feb 6 - Feb 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Salisbury (SBY)
The Shore House

The Shore House

2 out of 5
West Ocean City
Price was $2,671, price is now $2,217 per person
$2,217
per person
Feb 5 - Feb 9
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,120, price is now $981 per person
$981
per person
Feb 5 - Feb 9
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Mainstay Suites Ocean City West

Mainstay Suites Ocean City West

2.5 out of 5
West Ocean City
Price was $716, price is now $651 per person
$651
per person
Jan 25 - Jan 31
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $799, price is now $684 per person
$684
per person
Jan 25 - Jan 31
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Cambridge Inn

Cambridge Inn

2 out of 5
Price was $772, price is now $696 per person
$696
per person
Jan 25 - Jan 31
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Hampton Inn & Suites Ocean City West

Hampton Inn & Suites Ocean City West

2.5 out of 5
West Ocean City
Price was $771, price is now $696 per person
$696
per person
Jan 25 - Jan 31
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)

Top Flight Deals

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

Frontier Airlines
Thu, Feb 19 - Sun, Feb 22
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 19 hours ago
$68
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Feb 22, priced at $68 found 19 hours ago
Frontier Airlines
Wed, Jan 21 - Wed, Jan 28
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 5 hours ago
$68
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jan 28, priced at $68 found 5 hours ago
Spirit Airlines
Wed, Feb 11 - Wed, Feb 18
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$85 Roundtrip, found 16 hours ago
$85
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Feb 11 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Feb 18, priced at $85 found 16 hours ago
Frontier Airlines
Wed, Jan 7 - Thu, Jan 8
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$96 Roundtrip, found 5 days ago
$96
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Jan 7 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Jan 8, priced at $96 found 5 days ago