Search Deals onDagsboro Vacation Packages
Dagsboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Red Roof Inn & Suites Chestertown
Price was $545, price is now $465 per person
$465
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.

Beach Walk
Price was $4,388, price is now $3,707 per person
$3,707
per person
Dec 12 - Dec 19
found 5 hours 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.
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

Strawberry Crossroads
Price was $1,050, price is now $897 per person
$897
per person
Dec 12 - Dec 19
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this cabin in Pittsville. Enjoy free parking, laundry facilities, and a picnic area.
Low expectations were not met. This property is a mess. Our 6 bunk room had 1 VERY small table and 1 indoor chair. The outdoor chairs at were dirty and falling apart. The parking area and outdoor section of our "camp site" needed mowing. Goats and chickens roam the camp sites leaving animal crap everywhere that not only gets tracked into the cabins but also attracts flies that are relentless. The cabin (#2) has a loud rattle trap of a window AC unit that is also falling apart and comes complete with a thilthy filter that looks like it has never been cleaned. Windows in the cabin had no curtains or blinds. Bathrooms are gross and the garage was overflowing. Can't say there is any indication that this property is managed by anyone who has ever stayed at a campground. The attitude of those I interacted with was indifferent to the state of the place but they were walking around barefoot (true fact). The goats are a menace and aggressive and should not be permitted to roam free. Liabilities everywhere.
Reviewed on Sep 7, 2026

Comfort Inn & Suites Chestertown
Price was $649, price is now $562 per person
$562
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.
Convenient location, friendly staff, clean
Reviewed on Nov 8, 2026

Grand Hotel Ocean City Oceanfront
Price was $742, price is now $669 per person
$669
per person
Jan 15 - Jan 19
found 3 hours ago
Roundtrip non-stop 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.

Studio 6 Suites Pocomoke City, MD
Price was $785, price is now $717 per person
$717
per person
Dec 12 - Dec 19
found 16 hours 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.
Very nice staff. They are working hard to make it better. I definity would stay again.
Reviewed on Oct 29, 2026

Motel 6 Pocomoke City, MD
Price was $764, price is now $700 per person
$700
per person
Dec 12 - Dec 19
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.

Wingate by Wyndham Salisbury MD Airport North
Price was $911, price is now $836 per person
$836
per person
Dec 12 - Dec 19
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Parking
Reviewed on Nov 10, 2026
Dagsboro Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Dagsboro Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Tue, Feb 9 - Wed, Feb 24
LGA
LaGuardia
SBY
Salisbury - Ocean City Wicomico Regional
$527 Roundtrip, found 5 days ago
$527
Roundtrip
found 5 days ago

Wed, Feb 17 - Wed, Feb 24
EWR
Newark Liberty Intl. Airport
SBY
Salisbury - Ocean City Wicomico Regional
$549 Roundtrip, found 19 hours ago
$549
Roundtrip
found 19 hours ago

Fri, Jan 8 - Wed, Jan 20
SWF
Stewart Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$623 Roundtrip, found 2 days ago
$623
Roundtrip
found 2 days ago

Fri, Nov 13 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$643 Roundtrip, found 4 days ago
$643
Roundtrip
found 4 days ago
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