Ocean Pines Holidays

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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
Panoramic sunset over wetlands at Assateague Island in Maryland

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

Near it all OC beaches,Assateague island.Family-friendly white horse park

Near it all OC beaches,Assateague island.Family-friendly white horse park

Ocean Pines MD
10/10 Exceptional! (44 reviews)
The place was clean, comfortable, and very welcoming, and the host made sure we had everything we needed. Even though the weather was a bit misty and foggy during our visit, it actually made the experience feel peaceful and cozy. The location is great, close to the beaches and Assateague Island, ...

Reviewed on 9 Mar 2026

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Near it all OC beaches,Assateague island.Family-friendly white horse park
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
The price is NZ$126 per night from 12 Apr to 13 Apr
NZ$126
12 Apr - 13 Apr
includes taxes & fees
9/10 Wonderful! (3,474 reviews)
I stayed one night there and it’s my third time I reserved this hotel, so clean, big room , bed more comfortable, friendly staff.

Reviewed on 31 Mar 2026

Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
Fully refundableReserve now, pay when you stay
The price is NZ$190 per night from 7 Apr to 8 Apr
NZ$190
7 Apr - 8 Apr
includes taxes & fees
8.8/10 Excellent! (2,365 reviews)
Room was well appointed. Had newly renovated everything. The bones of this building are older, but everything is very nice.

Reviewed on 30 Mar 2026

Princess Royale Oceanfront Resort
See all 9,834 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.

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

GlenRiddle Golf Club

Enjoy a round of golf in Berlin at GlenRiddle Golf Club. Wander through the seaside and beautiful beaches in this family-friendly area.

GlenRiddle Golf Club

Carey Marina

Explore the waterfront of Carey Marina and enjoy other activities such as golfing in Berlin. Stroll along the seaside or discover the breathtaking sunrises in this family-friendly area.

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