Ocean Pines Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Ocean Pines Holiday

Embark on your next big adventure with one of our Ocean Pines holiday packages. Spend your time discovering this neighbourhood's countless delights, such as its golfing. Kick start your trip to Ocean Pines with a visit to nearby attractions such as Casino at Ocean Downs, Ocean Pines Golf and Country Club and River Run Golf Club. No matter your travel goals or the size of your budget, booking your perfect Ocean Pines holiday is easy with Expedia.

Black Friday Sale

Save up to 40% on select hotels
Book now

Our guide on where to stay in Ocean Pines

Find the best Ocean Pines areas and neighborhoods for the activities you enjoy most. Learn more about Ocean Pines
Default Image

Assateague Pointe

Though Assateague Pointe may not have many top sights, you can venture to the surrounding area to see attractions like Frontier Town Water Park and Golf and Ocean City Inlet.

Find hotels in Assateague Pointe

Our pick of the best Ocean Pines Hotel Deals

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
The price is AU$130 per night from 28 Dec to 29 Dec
AU$130
28 Dec - 29 Dec
includes taxes & fees
9/10 Wonderful! (1,586 reviews)
A nice spot with great views of the beach and boardwalk. A touch dated, the tech is behind by about 4 years, so no USB-C ports or streaming apps. But you’ll be too busy sleeping or out and about to notice. Good location near a lot of restaurants within walking distance but about a 30 minute walk ...

Reviewed on 19 Nov 2025

Hyatt Place Ocean City / Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
The price is AU$148 per night from 10 Dec to 11 Dec
AU$148
10 Dec - 11 Dec
includes taxes & fees
8.6/10 Excellent! (2,274 reviews)
Staff was great

Reviewed on 17 Nov 2025

Princess Royale Oceanfront Resort
Fenwick Inn

Fenwick Inn

3 out of 5
13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,996 reviews)
The room was very clean and the staff was friendly and helpful.

Reviewed on 18 Nov 2025

Get rates
Fenwick Inn
See all 9,716 properties in Ocean Pines
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Ocean Pines holiday package cost?
Get your credit card ready, because a trip to Ocean Pines starts from a tempting . When you combine your flights, hotels and more into a package, you'll land the best deals.
How do I get a cheap travel package to Ocean Pines?
Secure flights that fit in with your schedule, add a hotel room to your booking and watch the savings stack up with an Ocean Pines holiday package. It's as simple as that! From flights and hotels to rental cars and activities, Expedia is where your cheap getaway begins. And with over 550 partner airlines and 1 000 000 hotel options around the world to select from, you'll never be short of choice.
Where should I stay in Ocean Pines?
With loads to discover in Ocean Pines, we recommend you book a room in a hotel close to its attractions. Casino at Ocean Downs, Ocean Pines Golf and Country Club and River Run Golf Club are some fascinating ones to put on your must-see list.
What are the top hotels in Ocean Pines?
Lock in a room at Cosy Ocean Pines Cottage: Swim. It's one of this neighbourhood's most popular properties. Another reputable option in Ocean Pines is Cabin - Wonderful Wooded Gem With Free Wifi.
How far in advance should I book my Ocean Pines holiday?
To bag cheap prices, book as early as you can. Air carriers usually advertise flights, along with some of the lowest fares, up to 12 months prior to departure. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you're in need of a last-minute getaway in Ocean Pines, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia Ocean Pines travel package include?
It comes down to what type of trip you want to have. Ocean Pines holiday deals can include flights, hotels and car rentals. You can mix and match to create the bundle that suits you. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking an Ocean Pines travel package?
When you book your hotels, flights and car rentals together, you'll walk away with awesome discounts. Whether you're organising an island getaway in a villa or prefer to stay in a fancy hotel in the city, Expedia can make it happen for less.
Can I choose my airline with an Ocean Pines Expedia holiday package?
Yes — that's the beauty of an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 partner airlines around the world, so you have options galore when putting together your Ocean Pines getaway.
If I'm not able to travel, can I cancel my Ocean Pines holiday package?
Yes, you can cancel your Ocean Pines booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

Discover the most popular places to visit in Ocean Pines

Frontier Town Water Park and Golf

Frontier Town Water Park and Golf

Bring your family to Frontier Town Water Park and Golf and enjoy some excitement at this theme park in Berlin. Stroll along the beautiful beaches in this family-friendly area or seek out the golf courses.

Frontier Town Water Park and Golf

Eagle's Landing Golf Course

Enjoy a round of golf in Berlin at Eagle's Landing Golf Course. Stroll along the seaside or discover the breathtaking sunrises in this family-friendly area.

Eagle's Landing Golf Course
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.