Dagsboro Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Mary Pat Collins

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Dagsboro Holiday

Our pick of the best Dagsboro Hotel Deals

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street, Ocean City, MD
8.4/10 Very Good! (1,990 reviews)
"We came for our honeymoon and loved everything about this resort!! We were given a free room upgrade and our view was breathtaking. The location and atmosphere was fantastic. We plan to return next year!"

Reviewed on 12 Aug. 2025

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Princess Royale Oceanfront Resort
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
9/10 Wonderful! (3,092 reviews)
"Without providing breakfast, the hotel price seems a bit expensive."

Reviewed on 11 Aug. 2025

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Grand Hotel Ocean City Oceanfront
Fenwick Inn

Fenwick Inn

3 out of 5
13801 Coastal Highway, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is NZ$391 per night from 29 Aug to 30 Aug
NZ$391
29 Aug - 30 Aug
includes taxes & fees
8.6/10 Excellent! (1,978 reviews)
"Comfortable room and very convenient to beach. Didn’t impact me, but the breakfast was extremely busy and people were waiting awhile for the elevator. If you don’t mind using the stairs, it’s often quicker."

Reviewed on 12 Aug. 2025

Fenwick Inn
See all 13,707 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.

Frequently asked questions

How much does a Dagsboro holiday package cost?
You'll find cheap prices on Expedia for your Dagsboro break. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Dagsboro costs.
What are the cheapest months to go to Dagsboro?
Plan your trip for the low season and you're likely to find cheap Dagsboro holiday packages. Keep in mind that school holiday periods and local events and festivals can impact prices, so do some research before you go.
How many days is enough for Dagsboro?
Typically, a handful of days is enough to tick off the main attractions during your Dagsboro holiday. But if you prefer to have some time to rest or go on day tours, think about extending your trip.
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 holiday package as early as possible.
Is it cheaper to book a Dagsboro holiday as a package?
You can enjoy significant savings on your next Dagsboro getaway by booking a tailored holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday 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.
How to plan a trip to Dagsboro?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Dagsboro.
  2. Budget wisely: As well as the cost of your stay, you should consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could arise during your trip to Dagsboro.
  3. Decide how long to go for: Now that you know more about Dagsboro, you can figure out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Dagsboro holiday package that brings all your bookings together.

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