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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 $831, price is now $771 per person
$771
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.

Beach Walk

Beach Walk

2 out of 5
Price was $3,383, price is now $2,859 per person
$2,859
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.

Reviewed on Oct 13, 2026

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Price was $1,056, price is now $935 per person
$935
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Salisbury (SBY)
Book a stay at this beach hotel in Bethany Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bethany Beach Boardwalk and Bethany Beach Bandstand are located nearby.

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $905, price is now $815 per person
$815
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Salisbury (SBY)
Book a stay at this beach hotel in Fenwick Island. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maryland Beach and Bethany Beach Boardwalk are located nearby.

Wingate by Wyndham Salisbury MD Airport North

Wingate by Wyndham Salisbury MD Airport North

3 out of 5
Price was $887, price is now $813 per person
$813
per person
Dec 6 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Salisbury. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Eastern Shore Baseball Hall of Fame Museum and Arthur W. Perdue Stadium are located nearby.
Star is friendly, hotel leaves a lot to be desired.

Reviewed on Oct 10, 2026

Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $848, price is now $785 per person
$785
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Price was $946, price is now $876 per person
$876
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, 4 restaurants, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Miramar Condominiums

Miramar Condominiums

2 out of 5
Price was $1,451, price is now $1,347 per person
$1,347
per person
Dec 6 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 Ocean City Beach are located nearby.

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $946, price is now $876 per person
$876
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Salisbury (SBY)
Wingate by Wyndham Salisbury MD Airport North

Wingate by Wyndham Salisbury MD Airport North

3 out of 5
Price was $1,037, price is now $983 per person
$983
per person
Nov 25 - Nov 28
found 1 hour ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Salisbury (SBY)
Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

3 out of 5
Downtown Ocean City
Price was $941, price is now $921 per person
$921
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Salisbury (SBY)
Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland

3 out of 5
Price was $1,051, price is now $1,035 per person
$1,035
per person
Nov 25 - Nov 28
found 1 hour ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $843, price is now $763 per person
$763
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Salisbury (SBY)
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $3,383, price is now $2,859 per person
$2,859
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 $1,056, price is now $935 per person
$935
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Salisbury (SBY)
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $905, price is now $815 per person
$815
per person
Dec 6 - Dec 11
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Salisbury (SBY)

Top Flight Deals

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

Frontier Airlines
Wed, Dec 2 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$46 Roundtrip, found 1 hour ago
$46
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Dec 5, priced at $46 found 1 hour ago
Frontier Airlines
Thu, Nov 19 - Tue, Dec 8
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 8, priced at $58 found 1 day ago
Frontier Airlines
Wed, Dec 2 - Mon, Dec 14
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, found 5 hours ago
$87
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Dec 14, priced at $87 found 5 hours ago
Frontier Airlines
Tue, Nov 17 - Wed, Nov 18
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$88 Roundtrip, found 22 hours ago
$88
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Nov 18, priced at $88 found 22 hours ago