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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.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Price was $276, price is now $233 per person
$233
per person
Oct 13 - Oct 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Salisbury (SBY)
Stay at this motel in Dewey Beach. Enjoy free WiFi, free parking, and 20 beach bars. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach are located nearby.

Beach Walk

Beach Walk

2 out of 5
Save 100% on your flight
Price was $2,131, price is now $1,622 per person
$1,622
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Room wasn’t very clean when I arrived, I found dead beetles and toilet paper pieces on the floor. The bedding was stained.

Reviewed on Sep 2, 2026

Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $318, price is now $264 per person
$264
per person
Oct 13 - Oct 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

Majestic Hotel & Apartments

Majestic Hotel & Apartments

2 out of 5
Price was $2,158, price is now $1,873 per person
$1,873
per person
Nov 6 - Nov 9
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, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

The Shore House

The Shore House

2 out of 5
Price was $2,672, price is now $2,349 per person
$2,349
per person
Oct 9 - Oct 13
found 15 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Salisbury (SBY)
Stay at this motel in Ocean City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Beach and Ocean City Boardwalk are located nearby.
Only difficulty was that AI checked us in and if you get there after 11:30pm you can’t check in. I feel like that is something they should warn you about. But it was great for the price.

Reviewed on Sep 2, 2026

Marvel's on the Creek

Marvel's on the Creek

4 out of 5
Price was $1,075, price is now $955 per person
$955
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Book a stay at this beach B&B in East New Market. Enjoy free breakfast, free WiFi, and free parking. Popular attraction Bill Burton Fishing Pier State Park is located nearby.
Debby was a wonderful hostess at this beautiful bed and breakfast. She was very friendly, accomidating and made you feel very welcome. She served a delicious breakfast and even shared a secret recipe with me. Her home is beautifully decorated while the waterfront view is breathtaking. I highly recommend this unique bed and breakfast for your next travel experience.

Reviewed on Aug 23, 2026

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Price was $989, price is now $896 per person
$896
per person
Oct 9 - Oct 13
found 11 hours ago
Roundtrip non-stop flight included
Austin (AUS) 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 Ocean City Beach are located nearby.

Sahara Motel

Sahara Motel

2.5 out of 5
Price was $961, price is now $875 per person
$875
per person
Oct 9 - Oct 13
found 15 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Salisbury (SBY)
Stay at this motel 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 Ocean City Beach are located nearby.
Budget friendly great location and staff is wonderful. Cleanliness and upkeep of the hotel could do some work, but i've been coming down for years.

Reviewed on Sep 3, 2026

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Price was $276, price is now $233 per person
$233
per person
Oct 13 - Oct 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Salisbury (SBY)
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $2,131, price is now $1,622 per person
$1,622
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $318, price is now $264 per person
$264
per person
Oct 13 - Oct 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Salisbury (SBY)
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Price was $1,662, price is now $1,416 per person
$1,416
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was $1,068, price is now $952 per person
$952
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
The Shore House

The Shore House

2 out of 5
West Ocean City
Price was $3,209, price is now $2,803 per person
$2,803
per person
Oct 8 - Oct 13
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 $1,998, price is now $1,763 per person
$1,763
per person
Oct 10 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Marvel's on the Creek

Marvel's on the Creek

4 out of 5
Price was $1,075, price is now $955 per person
$955
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)

Top Flight Deals

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

Frontier Airlines
Tue, Oct 20 - Wed, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 1 day ago
$66
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 28, priced at $66 found 1 day ago
Frontier Airlines
Mon, Nov 2 - Mon, Nov 16
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$69 Roundtrip, found 18 hours ago
$69
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Nov 2 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 16, priced at $69 found 18 hours ago
Frontier Airlines
Sat, Nov 7 - Mon, Nov 16
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$78 Roundtrip, found 3 hours ago
$78
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Nov 7 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 16, priced at $78 found 3 hours ago
Frontier Airlines
Mon, Oct 5 - Tue, Oct 6
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$110 Roundtrip, found 3 hours ago
$110
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Oct 5 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 6, priced at $110 found 3 hours ago