Ocean Pines Holidays

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Your Ocean Pines Holiday

Let our Ocean Pines holiday packages take you to a destination where ever-lasting memories are waiting to be made. While it's especially known for its golfing, there's loads to love about this neighbourhood. 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. Whatever your dream Ocean Pines holiday looks like, you can turn it into reality with Expedia.

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

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street, Ocean City, MD
8.4/10 Very Good! (2,011 reviews)
"Everyone was so nice and it was really clean"

Reviewed on 17 Aug 2025

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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
The price is £156 per night from 6 Sept to 7 Sept
£156
6 Sept - 7 Sept
includes taxes & fees
8.6/10 Excellent! (1,964 reviews)
Average Stay, Good Location
"The stay was decent. Not great but, not terrible. Front desk personnel that I encountered were very nice. The rooms could've been cleaner, floors were definitely not mopped. Some towels were dirty. Enjoyed the Vista for drinks at night. Bartenders were very pleasant. Location is great since we like ..."

Reviewed on 17 Aug 2025

Fenwick Inn
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
2100 N Baltimore Ave, Ocean City, MD
9/10 Wonderful! (3,100 reviews)
"Property good condition, clean, Room service didn’t clean our room two days in a row with a hanging sign on dirt for service. Called desk and they sent someone to clean roo but only gave us towels. Seem like she was having a bad day. Other than that it was great. Location and breakfast served in ..."

Reviewed on 16 Aug 2025

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Grand Hotel Ocean City Oceanfront
See all 10,075 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Ocean Pines travel package cost?
Our Ocean Pines travel packages, which begin from just , are the best way to save big. Pick and choose your favourite hotels, flights and more to create a customized trip.
If I'm not able to travel, can I cancel my Ocean Pines travel package?
Yes, you can. We totally understand that even the best-laid plans can fail, so we're here to help if you need to make changes to your Ocean Pines travel package. It may be possible to amend or cancel your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Ocean Pines?
It's easy. Just bundle everything together. Hotels, flights and rental cars — combine whatever you need into an Ocean Pines travel package to save tons of cash. Score even bigger bargains when you add extras such as day tours to your booking. But that's not the only good part. You have the flexibility to tailor your trip your way. We offer more than 550 air carriers and 1,000,000 hotel options globally, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Ocean Pines holidays?
Good news! We do. Expedia has teamed up with online lender Klarna to help you easily pay for your holiday in instalments. Simply click on the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your trip. Be sure to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: If you want to pay for your getaway in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you come across an incredible deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you secure your getaway.

Where should I stay in Ocean Pines?
A trip to Ocean Pines wouldn't be complete without stopping by Casino at Ocean Downs, River Run Golf Club and Ocean Pines Golf and Country Club. Spend your nights near these sights and make sightseeing a breeze.
What are the top hotels in Ocean Pines?
Get your trip off to a great start by booking a stay at Atlantic Hotel. It's one of most sought-after hotels in Ocean Pines. Another leading option is Spacious Two - Story Home With Full Kitchen.
How far in advance should I book my Ocean Pines holiday?
Reserving your flights early with Expedia means one less thing to worry about. Most air carriers display prices up to 12 months prior to departure dates. This is generally the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Ocean Pines sometimes become available a few weeks before departure.
What does an Expedia Ocean Pines travel package include?
From flights and hotels to car rentals, Expedia can help you shape an Ocean Pines package that works for you. Heading away for a while? Consider a hotel, flight and rental car bundle. If you can only squeeze in a quick getaway, a hotel and flight deal may suit you better. Experiences can also be added after you've booked. Our travel packages make it easy to plan and save.
What should I know before booking an Ocean Pines travel package?
Our prices are always low. However, you'll score even more bargains when you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and tons of choice.
Can I choose my airline with an Ocean Pines Expedia travel package?
Yes, definitely. Expedia has over 550 airline partners to pick from worldwide. With all that choice, finding the ideal carrier to whisk you off to Ocean Pines won't be difficult.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.