Ocean Pines Holidays

Book a Hotel + Flight or Car together to unlock savings

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
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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 Beach.

Find hotels in Assateague Pointe

Top hotels in Ocean Pines

Fenwick Inn

Fenwick Inn

3 out of 5
13801 Coastal Highway, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is 5.787.075 ₫ per night from 3 Oct to 4 Oct
5.787.075 ₫
6.818.707 ₫ total
3 Oct - 4 Oct
includes taxes & fees
8.6/10 Excellent! (2,009 reviews)
"Shops nearby"

Reviewed on 30 Sept 2025

Fenwick Inn
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 2.219.700 ₫ per night from 20 Oct to 21 Oct
2.219.700 ₫
2.463.867 ₫ total
20 Oct - 21 Oct
includes taxes & fees
9/10 Wonderful! (1,551 reviews)
"Very clean and amazing staff"

Reviewed on 1 Oct 2025

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
9/10 Wonderful! (3,278 reviews)
"Yes wonderful view"

Reviewed on 30 Sept 2025

Get rates
Grand Hotel Ocean City Oceanfront
See all 9,987 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 1null000null000 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.

Popular places to visit

Main Street Berlin

Main Street Berlin

4/5(1 review)

During your trip to Berlin, you can find the perfect gifts to bring home at Main Street Berlin. Stroll along the beaches or experience the area's museums.

Main Street Berlin
Calvin B. Taylor House Museum

Calvin B. Taylor House Museum

You can spend time exploring the galleries in Calvin B. Taylor House Museum during your trip to Berlin. Amble around this family-friendly area's seaside or seek out the golf courses.

Calvin B. Taylor House Museum

Ocean Pines Golf and Country Club

Enjoy a round of golf in Berlin at Ocean Pines Golf and Country Club. Wander the seaside or discover the beautiful sunsets in this family-friendly area.

Ocean Pines Golf and Country Club