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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.
Microtel Inn & Suites by Wyndham Milford

Microtel Inn & Suites by Wyndham Milford

2.5 out of 5
Price was $633, price is now $585 per person
$585
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Live Cheap & Make Art Studios and Second Street Players - Riverfront Theatre are located nearby.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $845, price is now $724 per person
$724
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $730, price is now $659 per person
$659
per person
Dec 13 - Dec 20
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Book a stay at this beach hotel in Dewey Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach are located nearby.
Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
Price was $896, price is now $815 per person
$815
per person
Dec 13 - Dec 20
found 6 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this 3-star beach hotel in Dewey Beach. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach are located nearby.
Baymont By Wyndham Salisbury Md

Baymont By Wyndham Salisbury Md

2.5 out of 5
Price was $645, price is now $595 per person
$595
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this hotel in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Regal Salisbury and Centre at Salisbury are located nearby.
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3 out of 5
Price was $792, price is now $730 per person
$730
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star beach hotel in Ocean City. Enjoy free WiFi, a beach locale, and breakfast (surcharge). 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.
Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland

2.5 out of 5
Price was $671, price is now $622 per person
$622
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Fruitland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SU Indoor Tennis Center and Pemberton Historical Park are located nearby.
Hampton Inn Salisbury

Hampton Inn Salisbury

2.5 out of 5
Price was $670, price is now $621 per person
$621
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this hotel in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Centre at Salisbury and Regal Salisbury are located nearby.

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Microtel Inn & Suites by Wyndham Milford

Microtel Inn & Suites by Wyndham Milford

2.5 out of 5
Price was $633, price is now $585 per person
$585
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $845, price is now $724 per person
$724
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Baymont By Wyndham Salisbury Md

Baymont By Wyndham Salisbury Md

2.5 out of 5
Price was $645, price is now $595 per person
$595
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3 out of 5
Midtown Ocean City
Price was $792, price is now $730 per person
$730
per person
Dec 31 - Jan 4
found 1 day 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.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $730, price is now $659 per person
$659
per person
Dec 13 - Dec 20
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,404, price is now $1,208 per person
$1,208
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
Price was $896, price is now $815 per person
$815
per person
Dec 13 - Dec 20
found 6 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3 out of 5
Midtown Ocean City
Price was $823, price is now $766 per person
$766
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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, Dec 4 - Sun, Dec 7
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 4 hours ago
$60
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Dec 7, priced at $60 found 4 hours ago
Frontier Airlines
Thu, Dec 11 - Tue, Dec 16
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$62 Roundtrip, found 8 hours ago
$62
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Dec 11 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 16, priced at $62 found 8 hours ago
Frontier Airlines
Sat, Nov 22 - Mon, Dec 1
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$65 Roundtrip, found 7 hours ago
$65
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Nov 22 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Dec 1, priced at $65 found 7 hours ago
Spirit Airlines
Tue, Jan 13 - Sun, Jan 18
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$83 Roundtrip, found 3 hours ago
$83
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jan 18, priced at $83 found 3 hours ago