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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.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Price was $686, price is now $606 per person
$606
per person
May 23 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this apartment in Ocean City. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Price was $1,422, price is now $1,205 per person
$1,205
per person
May 23 - May 25
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. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Price was $795, price is now $682 per person
$682
per person
May 23 - May 25
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.
Boardwalk One

Boardwalk One

3 out of 5
Price was $800, price is now $688 per person
$688
per person
May 4 - May 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

2.5 out of 5
Price was $877, price is now $769 per person
$769
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. 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.
Americana Motor Inn

Americana Motor Inn

2.5 out of 5
Price was $805, price is now $707 per person
$707
per person
Jun 1 - Jun 4
found 10 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) 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 Ocean City Beach are located nearby.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Price was $965, price is now $853 per person
$853
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Maryland Beach are located nearby.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $738, price is now $658 per person
$658
per person
May 4 - May 8
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.

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 $800, price is now $688 per person
$688
per person
May 4 - May 8
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 $909, price is now $768 per person
$768
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Salisbury (SBY)
Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $917, price is now $794 per person
$794
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Salisbury (SBY)
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

2.5 out of 5
Midtown Ocean City
Price was $877, price is now $769 per person
$769
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $838, price is now $793 per person
$793
per person
May 9 - May 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $975, price is now $866 per person
$866
per person
May 9 - May 15
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 $935, price is now $833 per person
$833
per person
May 9 - May 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Hotel Monte Carlo Ocean City

Hotel Monte Carlo Ocean City

3 out of 5
Downtown Ocean City
Price was $871, price is now $802 per person
$802
per person
May 9 - May 15
found 1 day 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.

Frontier Airlines
Sat, Apr 18 - Mon, Apr 20
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, just found
$66
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 18 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Apr 20, priced at $66 just found
Frontier Airlines
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, May 2, priced at $68 just found
Frontier Airlines
Thu, Apr 30 - Sat, May 2
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$85 Roundtrip, found 2 days ago
$85
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, May 2, priced at $85 found 2 days ago
Spirit Airlines
Sat, Apr 18 - Wed, Apr 22
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Apr 18 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Apr 22, priced at $99 found 1 day ago