Ocean Pines Vacations from $718

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Your Ocean Pines Vacation

Embark on your next big adventure with one of our Ocean Pines vacation packages. Spend your time discovering this neighborhood'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 vacation is easy with Expedia.

The Latest Ocean Pines Vacation Packages

Price found within the past 48 hours. Click for updated prices.
OCHG Beachviews

OCHG Beachviews

Downtown Ocean City
$718
per person
Nov 21 - Nov 26
found 7 hours ago
Roundtrip flight included
San Juan (SJU) to Salisbury (SBY)
9.4/10 Exceptional! (9 reviews)
Sea Bay Hotel

Sea Bay Hotel

Midtown Ocean City
Save 100% on your flight
$2,216
per person
Nov 21 - Nov 26
found 13 hours ago
Roundtrip flight included
San Juan (SJU) to Salisbury (SBY)
8.2/10 Very Good! (673 reviews)
All was a very good stay

Reviewed on Sep 15, 2026

Miramar Condominiums

Miramar Condominiums

Downtown Ocean City
$1,037
per person
Nov 21 - Nov 26
found 13 hours ago
Roundtrip flight included
San Juan (SJU) to Salisbury (SBY)
9.4/10 Exceptional! (33 reviews)
Beautiful house and clean rooms! Perfectly equipped with everything!

Reviewed on Aug 28, 2026

The Shore House

The Shore House

West Ocean City
Save 100% on your flight
$2,671
per person
Oct 21 - Oct 27
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
6.6/10 (782 reviews)
Ants in the room, spiderwebs, insects, and old dirt in the stairways, TVs didn't work in the rooms- most channels didn't have subscriptions.. Check-in desk and Continental breakfast was at another hotel on the property. Beds were comfortable.

Reviewed on Sep 15, 2026

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

Midtown Ocean City
$749
per person
Nov 21 - Nov 26
found 13 hours ago
Roundtrip flight included
San Juan (SJU) to Salisbury (SBY)
8.4/10 Very Good! (53 reviews)
First, the good: The location was great. Quick walk to the beach, plenty of quick-stop type of places for ice and other items (you definitely need to order a sandwich at Anthony’s Liquors!). Short drive to lots of restaurants and other entertainment. The kitchen was well-appointed (bring coffee filters!) and the furnishings comfortable. The not-so-good: The floor was really grubby. My 10 month old grandson’s feet and hands were black within 15 min of crawling around on the floors, despite them appearing clean. The bathrooms were clean-ish. Otherwise, it was clean enough. Check in was confusing because you can’t check in till 5 and the office closes at 5, so ??? I was finally able to get in touch with someone who gave me instructions for accessing the keys to room. Bottom line: I’d stay here again.

Reviewed on Sep 9, 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
A sunset over a marshy landscape with a calm water body reflecting the sky.

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.

A wetland landscape with numerous small ponds surrounded by dense green vegetation.

Glen Riddle

While visiting Glen Riddle, you might make a stop by sights like Isle of Wight Bay and GlenRiddle Golf Club.

A long bridge over a body of water, surrounded by green vegetation and a clear blue sky with clouds.

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.

A sunset over a calm lake with reflections of trees and the sky.

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

Fenwick Inn

Fenwick Inn

13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
$82 nightly
$92 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (2,100 reviews)
"I like that you can tell it was recently renovated however my bathroom still had hair in it and 2 of the sheets had black stain and one of the pillows good thing we had a double bed. Also some of the towels were not clean properly which we got new ones. The last day of the stay the fire alarm went ..."

Reviewed on Sep 16, 2026

Fenwick Inn
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD
$94 nightly
$106 total
Oct 14 - Oct 15
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD
$116 nightly
$128 total
Oct 11 - Oct 12
Total with taxes and fees
Princess Royale Oceanfront Resort
See all 10,050 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.

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.
See properties

River Run Golf Club

Enjoy a round of golf in Berlin at River Run Golf Club. Wander the seaside or discover the beautiful sunsets in this family-friendly area.
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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.
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Things to do

Small Group Boat Tours of Chincoteague & Assateague - Wild Ponies

Boat Tours of Chincoteague & Assateague - Wild Ponies

$78
per adult
Boat Tours of Chincoteague & Assateague - Wild Ponies
Picture 19 for Activity From Chincoteague: Pony and Wildlife Boat Tour

Chincoteague: Premier Pony & Wildlife Small Group Boat Tour

$79
per adult
100% of travellers recommend
Chincoteague: Premier Pony & Wildlife Small Group Boat Tour
Ocean City: Ripley's Believe It or Not! + Mirror Maze

Ocean City: Ripley's Believe It or Not! + Mirror Maze

$28
per adult
Ocean City: Ripley's Believe It or Not! + Mirror Maze
See all activities in Berlin

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