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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 $556, price is now $518 per person
$518
per person
Nov 6 - Nov 9
found 8 hours 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.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,189, price is now $1,010 per person
$1,010
per person
Nov 6 - Nov 9
found 8 hours 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.
Boardwalk One

Boardwalk One

3 out of 5
Price was $778, price is now $691 per person
$691
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip 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.
Residence Inn by Marriott Salisbury

Residence Inn by Marriott Salisbury

3 out of 5
Price was $949, price is now $876 per person
$876
per person
Nov 6 - Nov 9
found 8 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.
Motel 6 Salisbury, MD

Motel 6 Salisbury, MD

2 out of 5
Price was $621, price is now $575 per person
$575
per person
Nov 6 - Nov 9
found 8 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 $1,732, price is now $1,604 per person
$1,604
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip 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.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $559, price is now $520 per person
$520
per person
Nov 6 - Nov 9
found 8 hours 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.
Courtyard by Marriott Salisbury

Courtyard by Marriott Salisbury

3 out of 5
Price was $937, price is now $880 per person
$880
per person
Oct 30 - Nov 3
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 WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. 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.
Motel 6 Salisbury, MD

Motel 6 Salisbury, MD

2 out of 5
Price was $621, price is now $575 per person
$575
per person
Nov 6 - Nov 9
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,189, price is now $1,010 per person
$1,010
per person
Nov 6 - Nov 9
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $778, price is now $691 per person
$691
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Residence Inn by Marriott Salisbury

Residence Inn by Marriott Salisbury

3 out of 5
Price was $949, price is now $876 per person
$876
per person
Nov 6 - Nov 9
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)

Top Flight Deals

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

Spirit Airlines
Sat, Nov 15 - Tue, Nov 18
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 6 days ago
$60
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Nov 18, priced at $60 found 6 days ago
Spirit Airlines
Thu, Oct 16 - Sun, Oct 19
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Oct 16 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Oct 19, priced at $80 found 1 day ago
Frontier Airlines
Thu, Oct 30 - Wed, Nov 5
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Nov 5, priced at $87 found 1 day ago
Frontier Airlines
Sat, Oct 25 - Thu, Oct 30
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 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 2 days ago