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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 $533, price is now $440 per person
$440
per person
Nov 14 - Nov 16
found 14 hours ago
Roundtrip flight included
Boston (BOS) 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.
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Price was $891, price is now $768 per person
$768
per person
Nov 6 - Nov 9
found 12 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.
Americana Princess Suites and Condos

Americana Princess Suites and Condos

2.5 out of 5
Price was $1,603, price is now $1,394 per person
$1,394
per person
Dec 11 - Dec 15
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this business-friendly condo in Ocean City. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Boardwalk One

Boardwalk One

3 out of 5
Price was $701, price is now $614 per person
$614
per person
Nov 6 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
Price was $1,057, price is now $945 per person
$945
per person
Nov 14 - Nov 16
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Perry Cabin Park and Higgins Yacht Yard and Marina are located nearby.
Motel 6 Salisbury, MD

Motel 6 Salisbury, MD

2 out of 5
Price was $694, price is now $633 per person
$633
per person
Nov 6 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this motel in Salisbury. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Regal Salisbury and Centre at Salisbury are located nearby.
Beach Walk

Beach Walk

2 out of 5
Price was $2,848, price is now $2,601 per person
$2,601
per person
Dec 11 - Dec 15
found 13 hours 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.
Residence Inn by Marriott Salisbury

Residence Inn by Marriott Salisbury

3 out of 5
Price was $1,025, price is now $936 per person
$936
per person
Nov 6 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $701, price is now $614 per person
$614
per person
Nov 6 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Price was $891, price is now $768 per person
$768
per person
Nov 6 - Nov 9
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Americana Princess Suites and Condos

Americana Princess Suites and Condos

2.5 out of 5
Downtown Ocean City
Price was $1,603, price is now $1,394 per person
$1,394
per person
Dec 11 - Dec 15
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
Price was $1,192, price is now $1,037 per person
$1,037
per person
Nov 6 - Nov 9
found 6 hours 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.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $827, price is now $707 per person
$707
per person
Nov 11 - Nov 16
found 11 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Price was $1,197, price is now $1,051 per person
$1,051
per person
Nov 22 - Nov 28
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Motel 6 Salisbury, MD

Motel 6 Salisbury, MD

2 out of 5
Price was $1,042, price is now $956 per person
$956
per person
Nov 22 - Nov 28
found 16 hours 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 $946, price is now $869 per person
$869
per person
Nov 22 - Nov 28
found 16 hours 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.

Frontier Airlines
Sat, Oct 18 - Sat, Oct 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$75 Roundtrip, found 14 hours ago
$75
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 25, priced at $75 found 14 hours ago
Spirit Airlines
Wed, Dec 3 - Tue, Dec 9
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$79 Roundtrip, found 3 days ago
$79
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Dec 3 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 9, priced at $79 found 3 days ago
Frontier Airlines
Fri, Nov 7 - Mon, Nov 10
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$80 Roundtrip, found 7 hours ago
$80
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 10, priced at $80 found 7 hours ago
Frontier Airlines
Sat, Oct 25 - Thu, Oct 30
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Oct 30, priced at $98 found 3 days ago