Ocean Pines, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Ocean Pines, Maryland on RentalSaver.com!

Ocean Pines Rentals

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VRBO
Vintage A-Frame at the Beach, with boat trailer parking & boat ramp privileges.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Architecture & beach lovers welcome. Only 4-miles from 63rd Street Beach in Ocean City, 5-pools, Golf, Tennis, Fishing & ...
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VRBO
From $390 per night (USD)
Expedia
57 Wood Duck is a Waterfront Dream in the Heart of Ocean Pines
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
When was the last time you were blown away by your Family Beach Vacation? 57 Wood Duck in the heart of Ocean Pines is su ...
From $390 per night (USD)
Expedia
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VRBO
Waterfront dream with boat lift. Come sail way!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Gorgeous, fully remodeled home on the Isle of Wright Bay. Minutes from bustling Ocean City, Maryland, but nestled in the ...
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VRBO
From $422 per night (USD)
Expedia
Snowbird Bay Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Snowbird Bay Cottage is a charming and cozy vacation home located in the White Horse Park community of Ocean Pines, Mary ...
From $422 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Reduced Family Rates 3BR, 2BA, 5 Pools, Back Yard, Private Ocean Beach Club, Sleeps 8, Free Tickets
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every ...
From $290 per night (USD)
VRBO
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Expedia
Ocean Pines-Borderlinks 48-AC, WIFI, Pool.
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Welcome to The Borderlinks community in Ocean Pines. This charming three bedroom, two bathroom, three level townhouse of ...
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Expedia
From $336 per night (USD)
VRBO
Rabbit Run-Located in the heart of Ocean Pines! Minutes away from OC!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
In the heart of Ocean Pines awaits the family vacation home you have been dreaming of! 36 Rabbit Run Lane is a fabulous ...
From $336 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Family Getaway in Peaceful Ocean Pines
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Ocean Pines, where adventure and relaxation meet! As soon as you pull up to our home, you'll immediately feel ...
From $494 per night (USD)
Expedia
From $637 per night (USD)
VRBO
Canal-front dog-friendly home, shared pools, sports courts, views
Bedrooms:
3
Bathrooms:
3
Sleeps:
11
Turtle Shores-22 Boston Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $637 per night (USD)
VRBO
$Quaint A-frame home with tennis court, pool, washer\/dryer, & WiFi$
From $444 per night (USD)
Expedia
Quaint A-frame home with tennis court, pool, washer\/dryer, & WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A Tale of Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $444 per night (USD)
Expedia
From $709 per night (USD)
VRBO
Cozy Cottage in Ocean PInes MD
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our charming 3-bedroom, 1-bath cottage nestled in the beautiful community of Ocean Pines. This vacation renta ...
From $709 per night (USD)
VRBO
From $550 per night (USD)
Expedia
Canalside home with lovely deck, central AC, WiFi, and shared pools
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Drawbridge Rd 38 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $550 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Martinique Beach Retreat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
PERSONAL RESERVATION SPECIALIST AVAILABLE 24/7 FREE LINENS & TOWELS PROVIDED! Welcome to our newly renovated beach hom ...
From $561 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Peace, Quiet and Serenity 12 miles from the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Bring your family and enjoy a large home with a beautiful sun porch, and fenced-in backyard. Enjoy crabs on the back de ...
From $301 per night (USD)
Expedia
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VRBO
Jumpstart your ultimate beach getaway at this impressive 3-BR, 2-BATH house!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come to Camelot in Ocean Pines! Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat h ...
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VRBO
$Gorgeous home with an enclosed yard, grill, fireplace, chef's kitchen, AC, & W\/D$
From $306 per night (USD)
Expedia
Gorgeous home with an enclosed yard, grill, fireplace, chef's kitchen, AC, & W\/D
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
The Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $306 per night (USD)
Expedia
From $592 per night (USD)
VRBO
Birdnest Beach Bungalow *Dog Friendly*
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Indulge in coastal bliss at our enchanting dog friendly 3-bedroom Ocean Pines retreat. Nestled in a serene location, thi ...
From $592 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Incredible Bayfront Home with Amazing Sunsets! A warm home with lots of space
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A very warm home for three couples or a family of 6. Three bedrooms and three and a half bathrooms. Nice open floor pl ...
From $353 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Ocean Pines Chalet !
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Nestled in the tranquil Ocean Pines, MD, Ocean Pines Chalet is a picturesque 4-bedroom, 3.5-bath haven exuding coastal c ...
From $570 per night (USD)
VRBO
From $365 per night (USD)
Expedia
Cozy home in Ocean Pines minutes away from beach, golf and more
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our charming retreat in Ocean Pines, Maryland! Nestled amidst the serene beauty of the Eastern Shore, our co ...
From $365 per night (USD)
Expedia
From $691 per night (USD)
VRBO
Ocean Pines Waterfront Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Welcome to your perfect waterfront retreat in Ocean Pines on a quiet cul-de-sac! This beautifully renovated home boasts ...
From $691 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Coastal Chic Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
PERSONAL RESERVATION SPECIALIST AVAILABLE 24/7 FREE LINENS & TOWELS PROVIDED! Escape to our coastal chic beach retreat ...
From $397 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Cozy Home Away From Home Available July 1, 2024
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
What you have been looking for... Coming soon to rent, furnished, July, Aug, Sept, & Oct. A memorable, cozy rancher, 3 ...
From $335 per night (USD)
VRBO
From $624 per night (USD)
Expedia
Ocean Pines 3BR 2BA Canal Front Home with Sunroom
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: Welcome to Qwack House where you can watch the ducks on the canal right out back of the home. Beautiful update ...
From $624 per night (USD)
Expedia
$Living ,dining ,family rooms for large families\nLarge driveway.EV car charging$
From $483 per night (USD)
VRBO
Living ,dining ,family rooms for large families\nLarge driveway.EV car charging
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This house is great for multiple families with many kids , Large Deck and barbecue fishing or boating in the cross str ...
From $483 per night (USD)
VRBO
From $446 per night (USD)
Expedia
The Mariner-Non Group Rental-5 Bedrooms, 3.5 Bathrooms, Sleeps 10
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
The Mariner will be your home away from home while vacationing on the east coast. This spacious 5-bedroom, 3.5-bathroom ...
From $446 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Ocean Pines 3 BR 2 Bath Screened Porch Central AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
2 Futon Chairs Exceptionally Renovated 3 Bedroom 2 Bath House with Enclosed Porch off Rec Room * Covered Front Porch * G ...
From $342 per night (USD)
VRBO
From $954 per night (USD)
Expedia
Beautiful 4 Bedroom Home on the water in Berlin!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
An action-packed getaway without the traffic crowds or hustle and bustle of Ocean City! Located right by Ocean Pines thi ...
From $954 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Whaler's Cottage close to nature
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This cozy retreat features a private entrance, a comfortable living area, and a well-equipped kitchen. The bedroom offer ...
From $180 per night (USD)
VRBO
From $888 per night (USD)
Expedia
Dolphins Chance beautiful waterfront
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape to your perfect retreat in Ocean Pines, MD! This beautiful waterfront home features 4 bedrooms and sleeps up to 1 ...
From $888 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Lord Guy Retreat in Ocean Pines 3bd
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Welcome to your perfect getaway in Ocean Pines, Maryland! This beautifully renovated 3-bedroom house offers modern ameni ...
From $370 per night (USD)
VRBO
From $487 per night (USD)
Expedia
Pet-Friendly Waterfront 3BR in Ocean Pines – Near OCMD, Porch & Canal Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Heron Hideaway, a beautifully remodeled waterfront vacation rental in Ocean Pines, MD, just minutes from the ...
From $487 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Seabright Townhouse 18 - Golf, Beach, Family & Relaxation. ENTIRE SUMMER SEASON!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Memorial begins Monday May 26th to Labor Day, Monday, September 1st. We are available to book 90 days or longer. Availab ...
From $392 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Ocean Pines 2BR 1BA Cottage with Fire Pit
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Pint-sized, pet friendly cottage close to everything, the perfect, quiet little sanctuary. Full kitchen in cas ...
From $319 per night (USD)
Expedia
From $900 per night (USD)
VRBO
Coastal Charm Oasis!
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Escape to our charming three-bedroom, two-bathroom vacation rental in beautiful Ocean Pines, MD. Perfectly situated just ...
From $900 per night (USD)
VRBO
From $382 per night (USD)
Expedia
4-bedroom chalet in lovely Ocean Pines with WiFi, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Bring the whole family (or families) to this great place with lots of room for fun. Royal Oaks Chalet is located in the ...
From $382 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Waterfront townhome on the golf course with private deck, & paid-access pools
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Borderlinks 20 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $416 per night (USD)
VRBO
From $836 per night (USD)
Expedia
Sea La Vie at the Inn on Turville Creek
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Sea La Vie is the luxury, custom built home located at the Inn on Turville Creek. The home was in 2020 and features 4 be ...
From $836 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Daybreak Cottage at the Inn on Turville Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Inn on Turville Creek offers 6 one-bedroom, waterfront cottage suites. Each tastefully appointed and sleep 4. Your ...
From $248 per night (USD)
VRBO
From $243 per night (USD)
Expedia
The Drift Inn Cottage at the Inn on Turville Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cottage is a charming one-bedroom suite at the Inn on Turville Creek. Whether you're looking for peace and quiet or sun ...
From $243 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Sunset Cove Cottage at the Inn on Turville Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
All of the conveniences of home but surrounded by nature, entertainment, and exciting activities.The Inn on Turville Cre ...
From $254 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Coral Tides at the Inn on Turville Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
All of the conveniences of home but surrounded by nature, entertainment, and exciting activities.The Inn on Turville Cre ...
From $247 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Seabreeze Cottage at the Inn on Turville Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy your coffee on the front covered porch watching the boats head down the creek for a day of fun in the sun. All ...
From $240 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Coconut Grove Cottage at the Inn on Turville Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy your coffee on the front covered porch watching the boats head down the creek for a day of fun in the sun. The In ...
From $244 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Home A Wave From Home-3 Bedrooms, 2 Baths, Sleeps 6, Non Group Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New for the 2025 season! Be one of the first to make your family beach memories here! New LVP flooring installed in the ...
From $367 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Spacious Family Home: 9 Mi to Ocean City Boardwalk
Bedrooms:
3
Bathrooms:
7
Sleeps:
11
2 Well-Stocked Kitchens | Board Game & Movie Nights | 4 Mi to Ocean Downs Casino Experience the best of the Maryland co ...
From $356 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Charming 3-bedroom mobile home with WiFi, AC in Ocean Pines
Bedrooms:
1
Bathrooms:
3
Sleeps:
20
Located in Ocean Pines, this charming mobile home is a dream. With 3 cozy bedrooms including a queen bed, bunk bed, and ...
From $222 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Beachy Pines-3 Bedrooms, 2 Bathrooms, Sleeps 6-Non-Group Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New for the 2025 rental season! This cozy 3-bedroom, 2-bathroom home is a great place to spend your beach vacation. With ...
From $330 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Modern Comfort meets coastal Charm! New Listing!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
NEW LISTING ALERT! Welcome to your perfect getaway at our beautifully designed vacation rental in Ocean Pines! This new ...
From $674 per night (USD)
VRBO
From $260 per night (USD)
Expedia
3-Bed, 2-Bath Home in Ocean Pines, MD – Just 15 Minutes from Ocean City Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to your home away from home in Ocean Pines, MD! This beautifully renovated three bedroom, two bath house sits on ...
From $260 per night (USD)
Expedia
From $324 per night (USD)
VRBO
The Blue Crab-Non-Group Rental-3 Bedrooms, 2 Bathrooms, Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New for the 2025 rental season! Pack up the family, head to the beach, and begin your vacation at The Blue Crab home. Th ...
From $324 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Three Bedroom Waterfront Home in Ocean Pines
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The Space: Large waterfront home in Ocean Pines, Maryland. This home offers three bedrooms, two full-bathrooms, one hal ...
From $470 per night (USD)
Expedia
$Serene Ocean Pines home w\/private deck all-season room & fully stocked kitchen$
From $358 per night (USD)
VRBO
Serene Ocean Pines home w\/private deck all-season room & fully stocked kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
22 Harpoon Rd Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $358 per night (USD)
VRBO
From $124 per night (USD)
Expedia
Skipjack Beach Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
FREE LINENS & TOWELS PROVIDED! Skipjack Beach Cottage is your perfect family beach retreat! Every inch of this home has ...
From $124 per night (USD)
Expedia
From $590 per night (USD)
VRBO
Teal Bay Getaway- Waterfront, 2 Masters, Pet Friendly, 5+ Bedrooms, Sleeps 17+
Bedrooms:
4
Bathrooms:
6
Sleeps:
18
Relax in this spacious 5 + bedroom, 3.5-bath Ocean Pines home, minutes from Ocean City and Assateague Island. Perfect fo ...
From $590 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Beautiful Ocean Pines home with screened porch, grill & fully stocked kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Smiling Octopus Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $317 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Private Dock, Hot Tub: Waterfront Ocean Pines Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
On-Site Bay Access | Patio w/ Al Fresco Dining Area | Furnished Deck Your bayside retreat awaits at this 2-bedroom + lo ...
From $365 per night (USD)
VRBO
$3BR Resort-View Condo w\/ Private BBQ & Parking$
From $503 per night (USD)
Expedia
3BR Resort-View Condo w\/ Private BBQ & Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: 》Hit '♡ Save' to plan your getaway at this cozy, family-friendly condo, perfect for relaxation and adventure! ...
From $503 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Whaler's Cabin minutes from Ocean City
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This spacious 3-bedroom, 2-bath home in peaceful Ocean Pines, MD, offers a relaxing retreat just minutes from Ocean City ...
From $277 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Ocean Pines Hideaway
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This 3-bed, 2-bath home in Ocean Pines sleeps 8 and is ideal for a beach getaway. The spacious interior includes a fully ...
From $380 per night (USD)
Expedia
From $289 per night (USD)
VRBO
8 Mi to Beach: Ocean Pines Home Near Marina & Golf
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Ocean Pines Amenities (w/ On-Site Fees) | Deck w/ Dining Table | Gas Grill (Propane Provided) Go on a beach retreat to ...
From $289 per night (USD)
VRBO
From $542 per night (USD)
Expedia
Calm On The Creek-Non Group Rental-Sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
New for the 2025 season! Enjoy this 2-story vacation home located on the water in Ocean Pines. Ocean Pines has everythin ...
From $542 per night (USD)
Expedia
From $382 per night (USD)
VRBO
The Pines and Sea A-Frame
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your next seaside escape at the Pines and Sea A-Frame. Nestled in the peaceful Ocean Pines community, this ch ...
From $382 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Cozy 2-bedroom waterfront bungalow with crabbing pier and boat ramp
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Get ready to relax in this 2-bedroom bungalow on the bay across from Ocean City. This property offers a beautiful escape ...
From $186 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Cozy, family friendly 4 bed, 3 bath. Large driveway and spacious new deck.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Great quiet location, close to the action but far enough away to avoid the hustle and bustle of Ocean City. Relax with ...
From $309 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Coastal Colonial Charm located in Ocean Pines
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 2 story colonial home is centrally located in the Ocean Pines Community. Safe, family friendly community with acce ...
From $342 per night (USD)
Expedia
From $126 per night (USD)
VRBO
cottage, community pool, playground, boating, crabbing kayaking and fishing!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Two Bedrooms, queen mattresses, kitchen, living room, family room breakfast area ,dining room and bath. 5 min walk to po ...
From $126 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Ocean Pines Dog Friendly Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Indulge in the perfect family getaway at this pet-friendly Ocean Pines cottage, where your furry companions are always w ...
From $431 per night (USD)
Expedia
From $533 per night (USD)
VRBO
OCMD Family Beach Retreat
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
This is the perfect beach home getaway with 6 Br plus 3 full baths and outdoor shower. Kitchen is fully equipped with ...
From $533 per night (USD)
VRBO
From $366 per night (USD)
Expedia
Cozy house in Ocean pines, only 10 mins away from Ocean City.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
As you step inside, you'll be greeted by an open concept living space that seamlessly connects the living room, dining a ...
From $366 per night (USD)
Expedia
$Rhapsody in Blue Beach Cottage in Ocean Pines OC MD w\/ Beach Club Parking Pass$
From $311 per night (USD)
VRBO
Rhapsody in Blue Beach Cottage in Ocean Pines OC MD w\/ Beach Club Parking Pass
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Welcome to the blue beach bubble. Located just 5 miles from Ocean City and 25 minutes from Assateague, our cottage is th ...
From $311 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Dog-friendly coastal escape with yard and central AC - community amenities
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Teal Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $387 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Ocean Pines- Great for large families!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Indulge in this stunning Ocean Pines home with an open floor plan, ideal for family gatherings. Accommodating up to 10 p ...
From $405 per night (USD)
VRBO
$Contemporary, spacious home with firepit, washer\/dryer, & central AC$
From $478 per night (USD)
Expedia
Contemporary, spacious home with firepit, washer\/dryer, & central AC
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
5 Whitecap Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $478 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Cottage on the Canal minutes from Ocean City, Assateague Island and Ocean Downs
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Canal front cottage perfect for relaxing and fun filled vacations in close proximity to Ocean City, Ocean Downs Casino a ...
From $368 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Cozy, Bright Beach Retreat In The Woods (Great for Pets & Kids!)
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Relax with the whole family at this peaceful woodsy retreat blocks from the water. With plenty of bright living space in ...
From $430 per night (USD)
Expedia
Click For Pricing
VRBO
Beautifully renovated bayfront home with deck, game room, fireplace & EV charger
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
Lookout Point Luxury Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
Click For Pricing
VRBO
From $521 per night (USD)
Expedia
Reduced Rates Family Fun 4BR, 4BA, 5 Pools, fantastic back yard, Private Ocean Beach Club, Sleeps 12
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every ...
From $521 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy Beach Getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the Cozy Beach Getaway in Ocean Pines North! Home located in a cul-de-sac in Ocean Pines, 10 minutes from Oce ...
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VRBO
From $407 per night (USD)
Expedia
Manklin Creek Retreat-Waterfront,3 Bedrooms, 2.5 Bathrooms, Sleeps 8, Non Group Rental
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Granite kitchen countertops and tile backsplash were installed in 2023. Make your vacation memories in this 3 bedroom, ...
From $407 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Fantastic gem near the beach with fast WiFi, shared pool, grill, central AC & WD
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Trinity Place Treasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $391 per night (USD)
VRBO
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Expedia
Sand & Surf @ 9 Stonemeadow OCEAN PINES
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Comfort and convenience at your fingertips! Come stay at Sand & Surf only 10 min from Ocean City, 15 min for Assateague ...
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Expedia
From $239 per night (USD)
VRBO
Serene Ocean PInes Cottage - Close to all area attractions!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our Peaceful Pines Retreat located in the amenity rich community of Ocean Pines! Whether you are looking for ...
From $239 per night (USD)
VRBO
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Expedia
Perfect beach getaway! 4-bdrm on canal by the bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Kick back and relax in this calm, stylish space where you can kayak or paddle board on the bay, jet ski to Ocean City or ...
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Expedia
From $726 per night (USD)
VRBO
Large Direct Bayfront Home with Great Amenities
Bedrooms:
5
Bathrooms:
5
Sleeps:
9
The Space: Amazing views in this large, direct bayfront home in Ocean Pines. The home offers over four-thousand square ...
From $726 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Modern and Updated Home in Ocean Pines- Oceans Calling only 8 miles away.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Check-in DIRECTLY AT PROPERTY, NO STOPPING AT A RENTAL OFFICE, Keyless Entry. Welcome to our little slice of heaven, loc ...
From $228 per night (USD)
Expedia
From $625 per night (USD)
VRBO
Annie's Dream-3 Bedrooms, 2.5 Bathrooms, Sleeps 10-Non Group Rental
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Beautiful and spacious 3 BR, 2 1/2 bath, single family home located on a canal in Ocean Pines. The home has over 3100 sq ...
From $625 per night (USD)
VRBO
From $502 per night (USD)
Expedia
A Pawfect Salty Hideaway-Non Group Rental-4 Bedrooms, 3 Bathrooms, Sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
In 2024 the owners installed a new stainless steel stove and microwave in the roomy kitchen. Make your vacation memorie ...
From $502 per night (USD)
Expedia
From $1272 per night (USD)
VRBO
Waterfront Home with views of OC Skyline!
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Welcome to your dream vacation rental - a luxurious 5-bedroom, 2.5-bathroom waterfront property with a private boat dock ...
From $1272 per night (USD)
VRBO
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Expedia
Waterfront oasis water sports of all kinds
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Ocean Pines property overlooking the Assawoman Bay. An oasis of birds, fish, turtles. There’s walking, biking path aroun ...
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Expedia
$Home with central AC, gas fireplace, washer\/dryer, firepit, & shared pools$
From $415 per night (USD)
VRBO
Home with central AC, gas fireplace, washer\/dryer, firepit, & shared pools
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Ocean Pines Fairway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $415 per night (USD)
VRBO
From $471 per night (USD)
Expedia
Waterfront oasis with 4 decks, grill, free WiFi, pool access, dock & central AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
14 Clipper on the Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $471 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Quiet townhome on the golf course with deck, central AC & paid-access pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Borderlinks 10 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $296 per night (USD)
VRBO
$Waterfront Ocean Pines Vacation Home w\/ Boat Dock!$
From $554 per night (USD)
Expedia
Waterfront Ocean Pines Vacation Home w\/ Boat Dock!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Indulge in coastal relaxation with a stay at this scenic seaside vacation rental in Ocean Pines, MD. Perfect for large f ...
From $554 per night (USD)
Expedia
$Ocean City Gateway: Modern 4BR\/2.5BA home, dog friendly$
From $434 per night (USD)
VRBO
Ocean City Gateway: Modern 4BR\/2.5BA home, dog friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Have fun with the whole family at our stylish Ocean City-convenient home! This wooded beach house boasts many modern upg ...
From $434 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Birdnest By The Bay - 3 bedrooms, 2 bathrooms, Sleeps 6, Non Group Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Enjoy this brightly decorated 3 bedroom and 2 bathroom home with huge 20 x 14 foot screen porch. Cook for the family out ...
From $327 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
There is nothing quite like getting your fill of quality time and sweet relaxation here in Ocean Pines, so make yourself ...
From $330 per night (USD)
VRBO
$O.P. Yacht Club Townhome\/ 3 Br\/Pool \/Marina \/ golf$
From $341 per night (USD)
Expedia
O.P. Yacht Club Townhome\/ 3 Br\/Pool \/Marina \/ golf
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Summary: Forget your worries in this spacious and serene space. Located in the middle of Ocean Pines and in walking dis ...
From $341 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Nice Three Bedroom Home in Popular Ocean Pines
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Space: Well-maintained PET FRIENDLY vacation home in the popular Ocean Pines resort community. This home offers thr ...
From $398 per night (USD)
VRBO
$Waterfront w\/Dock, Rooftop Terrace & 2 Kings$
From $853 per night (USD)
Expedia
Waterfront w\/Dock, Rooftop Terrace & 2 Kings
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Enjoy stunning views from every room in this bayside beauty located in the peaceful Ocean Pines community just 9 miles f ...
From $853 per night (USD)
Expedia

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Results: 283 Rentals