Search Deals on
Chestertown Vacation Packages

Build your package with 2 more options
Photo by Assya A

Chestertown Flight + Hotel Packages

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 $397, price is now $326 per person
$326
per person
Nov 16 - Nov 21
found 20 hours ago
Roundtrip flight included
Detroit (DTW) 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.
Americana Princess Suites and Condos

Americana Princess Suites and Condos

2.5 out of 5
Save 100% on your flight
Price was $1,611, price is now $1,113 per person
$1,113
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Harrington Welcome Inn

Harrington Welcome Inn

2.5 out of 5
Price was $788, price is now $564 per person
$564
per person
Nov 16 - Nov 21
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Salisbury (SBY)
Stay at this hotel in Harrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Harrington Raceway and Casino and Delaware State Fairgrounds are located nearby.
Boardwalk One

Boardwalk One

3 out of 5
Price was $914, price is now $710 per person
$710
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
OCHG Ocean Block 7-11

OCHG Ocean Block 7-11

3 out of 5
Price was $1,304, price is now $1,031 per person
$1,031
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Stay at this 3-star condo in Ocean City. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
OCHG Sand Dollars

OCHG Sand Dollars

3 out of 5
Price was $1,272, price is now $1,009 per person
$1,009
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Stay at this 3-star condo in Ocean City. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Price was $717, price is now $574 per person
$574
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star 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 Ocean City Beach are located nearby.
Comfort Inn & Suites Milford

Comfort Inn & Suites Milford

2.5 out of 5
Price was $502, price is now $409 per person
$409
per person
Nov 16 - Nov 21
found 20 hours ago
Roundtrip flight included
Detroit (DTW) 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.

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $587, price is now $522 per person
$522
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip 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 $717, price is now $574 per person
$574
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was $1,210, price is now $1,024 per person
$1,024
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
Price was $815, price is now $735 per person
$735
per person
Oct 21 - Oct 25
found 1 hour ago
Roundtrip 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.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $397, price is now $326 per person
$326
per person
Nov 16 - Nov 21
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Salisbury (SBY)
Harrington Welcome Inn

Harrington Welcome Inn

2.5 out of 5
Price was $788, price is now $564 per person
$564
per person
Nov 16 - Nov 21
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Salisbury (SBY)
Comfort Inn & Suites Milford

Comfort Inn & Suites Milford

2.5 out of 5
Price was $502, price is now $409 per person
$409
per person
Nov 16 - Nov 21
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Salisbury (SBY)
Home2 Suites by Hilton Lewes Rehoboth Beach

Home2 Suites by Hilton Lewes Rehoboth Beach

3 out of 5
Price was $491, price is now $407 per person
$407
per person
Nov 16 - Nov 21
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Salisbury (SBY)

Top Flight Deals

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

Spirit Airlines
Wed, Nov 12 - Thu, Nov 13
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Nov 12 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Nov 13, priced at $70 found 2 days ago
Spirit Airlines
Sat, Sep 27 - Mon, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$86 Roundtrip, found 23 hours ago
$86
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Sat, Sep 27 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 29, priced at $86 found 23 hours ago
Frontier Airlines
Thu, Oct 30 - Mon, Nov 3
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 3, priced at $90 found 1 day ago
Spirit Airlines
Fri, Sep 19 - Mon, Sep 22
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$101 Roundtrip, found 2 days ago
$101
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, Sep 19 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 22, priced at $101 found 2 days ago