Ocean Pines Vacation Packages
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Top Holiday Package Deals in Ocean Pines
Price found within the past 48 hours. Click for updated prices.
Princess Royale Oceanfront Resort
North Ocean City
CA $1,176
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Salisbury (SBY)
8.8/10 Excellent! (2,606 reviews)
Traveled with kids and we enjoyed ourselves overall. The pool and proximity to the rooms were perfect. We couldn't enjoy the beach as there's an overwhelming amount of jellyfish in the Ocean currently. My 7 year old got stung, so I wish there were signs to alert visitors. My only problem with the resort is that it's kid friendly, yet there was no emergency stations. However , once alerted that my child was stung, the staff were super responsive and helpful with suggesting and providing remedies. Overall great, family friendly resort. I would stay again, I would just do my research on jellyfish season.
Reviewed on Aug 20, 2026
Dunes Court
Midtown Ocean City
CA $976
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Salisbury (SBY)
8.4/10 Very good! (1,007 reviews)
Overall this was a pretty good place to stay! The location to the beach was the main selling point for me. I read the reviews and they all seemed good! Everything was pretty clean just a bit outdated with the carpet. Only thing I didn’t care for was the bedding. They came everyday and cleaned our room, made the beds and gave clean towels without asking. I would definitely stay here again!
Reviewed on Aug 19, 2026
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
Assateague Pointe
While Assateague Pointe isn't home to many top sights, Frontier Town Water Park and Golf and Ocean City Beach are some notable places to visit nearby.
Glen Riddle
1 out of top 10 points of interest in this area
While visiting Glen Riddle, you might make a stop by sights like Isle of Wight Bay and GlenRiddle Golf Club.
Bayside
Bayside might not have many top sights, but Frontier Town Water Park and Golf and Ocean City Beach are two attractions nearby that you can check out.
Downtown Berlin
Downtown Berlin might not have many top sights, but Casino at Ocean Downs and Frontier Town Water Park and Golf are two attractions nearby that you can check out.
Ocean Pines Hotel Deals
Princess Royale Oceanfront Resort
Oceanfront on 91st Street Ocean City MD
CA $162
CA $203 total
Sep 20 - Sep 21
includes taxes & fees
8.8/10 Excellent! (2,683 reviews)
"Traveled with kids and we enjoyed ourselves overall. The pool and proximity to the rooms were perfect. We couldn't enjoy the beach as there's an overwhelming amount of jellyfish in the Ocean currently. My 7 year old got stung, so I wish there were signs to alert visitors. My only problem with the ..."
Reviewed on Aug 20, 2026
Grand Hotel Ocean City Oceanfront
2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
CA $187
CA $209 total
Sep 20 - Sep 21
includes taxes & fees
9/10 Wonderful! (3,810 reviews)
"Didn’t see any staff other than on the front desk. It’s right on the beach, plenty of food, walk on boardwalk. Great view from the balcony."
Reviewed on Aug 20, 2026
Fenwick Inn
13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
CA $111
CA $145 total
Sep 14 - Sep 15
includes taxes & fees
8.8/10 Excellent! (2,091 reviews)
"The hotel was ok but l will never go to Ocean City again. It was so boring and the jellyfish kept most out of the water. The pool was nice and my hubby loved the hot tub. The staff was very nice and helpful. I would have liked better breakfast choices. I just disliked the area."
Reviewed on Aug 19, 2026
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 vacation package cost?
Get your credit card ready, because a trip to Ocean Pines starts from a tempting CA $609. 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 vacation 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 Cozy Ocean Pines Cottage: Swim. It's one of this neighborhood'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 vacation?
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 vacation 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 organizing 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 vacation 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 vacation 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.
Stay near popular Ocean Pines attractions
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.
River Run Golf Club
Enjoy a round of golf in Berlin at River Run Golf Club. Wander the seaside or discover the beautiful sunrises in this family-friendly area.
Manklin Meadows Racquet Center
Catch an event at Manklin Meadows Racquet Center during your trip to Berlin. Wander the seaside and beaches while you're in the area.
Things to do
Boat Tours of Chincoteague & Assateague - Wild Ponies
CA $110
per adult
Ocean City: Ripley's Believe It or Not! + Mirror Maze
CA $39
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.