Dagsboro Vacations from $397

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Your Dagsboro Vacation

Our Dagsboro vacation packages let you customize your own adventure. Tailor your getaway to your interests and needs and make the most of your time in this fabulous city. You'll want to go sightseeing during your trip to Dagsboro. Find time for big-name attractions such as Baywood Greens Golf Course, Nanticoke Indian Museum and 2nd Time Designs. Don't delay exploring this city any longer. Your ultimate Dagsboro vacation is a couple of clicks away with Expedia.

The Latest Dagsboro vacation packages

Price found within the past 48 hours. Click for updated prices.
St Michaels Inn

St Michaels Inn

2.5 out of 5
Price was $487, price is now $397 per person
$397
per person
Apr 17 - Apr 20
found 14 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8.2/10 Very Good! (1,003 reviews)
Room was fine. Breakfast was poor with two empty hot breakfast servers. Rest of food substandard. Staff was nice

Reviewed on Jan 18, 2026

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
Downtown St. Michaels
Save 100% on your flight
Price was $965, price is now $668 per person
$668
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.6/10 Exceptional! (369 reviews)
Friendly and attentive staff, good cleaning services

Reviewed on Oct 26, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,121, price is now $1,637 per person
$1,637
per person
Apr 7 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
7.6/10 Good! (95 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing

Reviewed on Oct 17, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,318, price is now $1,076 per person
$1,076
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was $822, price is now $683 per person
$683
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
6/10 (681 reviews)
Very helpful staff and clean property

Reviewed on Dec 2, 2025

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Dagsboro Hotel Deals

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
Fully refundable
$108 nightly
The price is $119 total per night from Mar 4 to Mar 5
$119 total
Mar 4 - Mar 5
Total with taxes and fees
8.8/10 Excellent! (2,342 reviews)
Beautiful place .

Reviewed on Feb 24, 2026

Princess Royale Oceanfront Resort
Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

3 out of 5
1 16th Street Ocean City MD
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $91 total per night from Mar 19 to Mar 20
$91 total
Mar 19 - Mar 20
Total with taxes and fees
9/10 Wonderful! (1,572 reviews)
Always a Good Stay....Carpets Need to be updated to Vinyl Flooring. Breakfast should be included Especially for Hyatt Member Card Holders. The Indoor Pool water was Chilly for Winter Stay.

Reviewed on Feb 22, 2026

Hyatt Place Ocean City / Oceanfront
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Mar 1 to Mar 2
$81 total
Mar 1 - Mar 2
Total with taxes and fees
9/10 Wonderful! (3,468 reviews)
Didn’t have any heat all night also smoking smell from our next door neighbors!! And they didn’t have working lights!!

Reviewed on Feb 24, 2026

Grand Hotel Ocean City Oceanfront
See all 13,161 properties in Dagsboro
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Dagsboro Vacation Packages

Dagsboro Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Salisbury - Ocean City Wicomico Regional Airport (SBY)
Population
860
Top Sights
Delaware Seashore State Park, Fenwick Island Beach and Bethany Beach Beaches

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Frequently asked questions

How much does a Dagsboro vacation package cost?
You'll find cheap prices from $397 on Expedia for your Dagsboro break. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Dagsboro costs.
What are the cheapest months to go to Dagsboro?
If you'd like to book a cheap Dagsboro vacation package, consider visiting in November, December and January. You'll typically find lower rates on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Dagsboro?
Typically, a handful of days is enough to tick off the major sights during your Dagsboro vacation. However, if you want to have some time to chill out or go on day tours, consider extending your itinerary.
How to find the best Dagsboro package deals?
Use Expedia's filter tool to find some great Dagsboro package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Dagsboro package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Dagsboro vacation as a package?
You can enjoy significant savings on your next Dagsboro getaway by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Dagsboro?
If you've got your Dagsboro travel dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Dagsboro vacation packages?
Your Dagsboro trip should be an escape from your busy life, not a source of money-related stress. So to give you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.