Ocean Pines Rentals
From $417 per night (USD)VRBO
Barefoot Pines Beach Retreat | Fire Pit + Grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Barefoot Pines Beach Retreat in Ocean Pines. Stylish 3BR, 2BA sleeps 6 with king, queen and twin tr ...
From $417 per night (USD)VRBO
From $716 per night (USD)Expedia
Coastal Pines Retreat | Beach Pass & Grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Blue Tides at Coastal Pines, a family-friendly retreat in the heart of Ocean Pines, Maryland. This ...
From $716 per night (USD)Expedia
From $473 per night (USD)VRBO
The Sandy Hook Retreat| Grill & Sunroom
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to The Sandy Hook Retreat, a relaxing 3BD/2BA coastal retreat in Ocean Pines, surrounded by parks, mar ...
From $473 per night (USD)VRBO
From $421 per night (USD)Expedia
Waterfront Getaway with Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Escape to our bright, tranquil canal-front house in Ocean Pines, perfect for large families and groups. This w ...
From $421 per night (USD)Expedia
From $2064 per night (USD)VRBO
Luxury Waterfront 8-Bedroom, 8.5-Bath Home
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 20
Summary: Escape to a rare direct bayfront masterpiece on a premier point lot in desirable Ocean Pines, Maryland. This s ...
From $2064 per night (USD)VRBO
From $442 per night (USD)Expedia
Stay at Riptide Retreat- Charming Getaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Awake to the call of seagulls and the sparkle of the bay at your doorstep. The Riptide Retreat blends the thrill of coas ...
From $442 per night (USD)Expedia
From $1060 per night (USD)VRBO
Spacious canal-front home with private dock, parking, and family-friendly amenities.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this canal-front Ocean Pines retreat featuring a private boat dock, ample parking, and peaceful waterfront vie ...
From $1060 per night (USD)VRBO
From $520 per night (USD)Expedia
Serenity in Ocean Pines | 1 Story Home with Backyard Grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Serenity in Ocean Pines, a warm and inviting 3-bedroom, 2-bath retreat made for easy coastal living ...
From $520 per night (USD)Expedia
From $457 per night (USD)VRBO
A Wave From it All | Screened Porch Outdoor Dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to A Wave from it All, your perfect coastal retreat in Ocean Pines. This spacious 3-bedroom, 2-bath ho ...
From $457 per night (USD)VRBO
From $334 per night (USD)Expedia
Pool + Bay Access! Home 13 Mi to Ocean City Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Gated Waterfront Community | Furnished Deck + Grill | 2 Mi to Golf | 5 Mi to Ocean Downs Casino Whether you’re looking ...
From $334 per night (USD)Expedia
From $357 per night (USD)VRBO
11 Mi to Ocean City Beach! Family-Friendly Haven
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Screened-In Sanctuary | 5 Community Pools, Bay Beach + Golf | 8 Mi to Main St Berlin Find the best of both worlds at th ...
From $357 per night (USD)VRBO
From $582 per night (USD)Expedia
Ocean Pines Getaway with Beach Pass
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Escape to our spacious 4-BR Ocean Pines home, perfect for families & groups! Enjoy a bright, coastal-themed in ...
From $582 per night (USD)Expedia
From $486 per night (USD)VRBO
Lighthouse Cottage | Ocean Pines, Golf & OC Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Book your 2026 Ocean Pines summer week before peak dates are gone. Lighthouse Cottage is a peaceful Ocean Pines vacation ...
From $486 per night (USD)VRBO
From $469 per night (USD)Expedia
Spacious 4-bed house in peaceful Ocean Pines - wooded near pool, bay, & ocean
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Stay comfortably in Ocean Pines at this 4-bedroom house; located in a peaceful wooded cul-de-sac, 10 minutes from beach ...
From $469 per night (USD)Expedia
From $544 per night (USD)VRBO
WATERFRONT HOME Ocean Pines Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Canal waterfront home in great community of Ocean Pines with deep water and direct access to open water. Bring your boat ...
From $544 per night (USD)VRBO
From $278 per night (USD)VRBO
Quiet family home- Deck, Trails & Water Sports
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Charming family retreat in Ocean Pines just minutes from pristine beaches and coastal waters. Enjoy boating, kayaking, p ...
From $278 per night (USD)VRBO
From $531 per night (USD)VRBO
Comfortable Home 5 Miles From the Beach, 10 beds!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Ideal for those who want to enjoy the beach, without spending a fortune on hotel rooms. A short drive or boat ride acros ...
From $531 per night (USD)VRBO
From $587 per night (USD)VRBO
Ocean Pines Retreat, Berlin, MD close to Ocean City and multiple golf courses
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Newly Remodeled 3-Bedroom Coastal Retreat in Ocean Pines Escape to this beautifully remodeled 3-bedroom, 2-bath home lo ...
From $587 per night (USD)VRBO
From $537 per night (USD)VRBO
Spacious 5-bedroom home in Ocean Pines , Walk to Pool, Beach & Parks, Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your perfect Ocean Pines getaway! Nestled on a quiet street in the desirable Swim & Racquet Club area, this s ...
From $537 per night (USD)VRBO
From $257 per night (USD)VRBO
Bright Golf Course Condo Near Ocean City
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Experience a laid-back golf course retreat! Immerse yourself in our bright and inviting end-unit, looking out onto the b ...
From $257 per night (USD)VRBO
From $306 per night (USD)VRBO
3-bedroom condo in an Ocean Community on a golf course
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Bring the whole family to this great place with lots of room for fun. Welcome to your cozy getaway with stunning water ...
From $306 per night (USD)VRBO
From $2012 per night (USD)VRBO
Luxury Waterfront Retreat, Private Dock, Pontoon Option, Golf, Pools, Beach Club
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to a beautifully furnished coastal retreat in the prestigious Tern's Landing neighborhood of Ocean Pines. Designe ...
From $2012 per night (USD)VRBO
From $387 per night (USD)VRBO
Down Bimini Lane: Family Retreat (7+) w HomeOffice
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Great for 2 couples (friends/in-laws) and kids. The property is in the Ocean Pines HOA, a 15-minute drive from Ocean Cit ...
From $387 per night (USD)VRBO
From $299 per night (USD)VRBO
Charming 3-bedroom house in Ocean Pines with WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Come enjoy all that the Maryland Eastern Shore has to offer at CrabbyPines in Ocean Pines. You may never leave this amen ...
From $299 per night (USD)VRBO
From $201 per night (USD)VRBO
Waterfront townhouse on the bay minutes from Ocean City and Assateague Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
2 bedroom 2 bath plus a loft that is located on the bay west of Ocean City, MD. Amenities include fishing pier for crab ...
From $201 per night (USD)VRBO
From $594 per night (USD)VRBO
Waterfront Getaway with Sunsets and Bald Eagles for Company
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Amazing waterfront jewel of a home with views across quiet deep waters to scenic wooded open space; there is a dock/jet ...
From $594 per night (USD)VRBO
From $326 per night (USD)VRBO
Coastal Oasis in Ocean Pines
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully decorated private mother-in-law suite (1,000 square feet) locked off from the rest of the house, across the ...
From $326 per night (USD)VRBO
From $212 per night (USD)VRBO
Peaceful, pet and family-friendly beach retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape the busy and hurried life in our Ocean Pines home. Nestled among the trees, enjoy your coffee peacefully, sitting ...
From $212 per night (USD)VRBO
From $599 per night (USD)VRBO
An escape for all seasons
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Beautiful, newly renovated, four bedroom house with open floor plan at the mouth of a canal located in Ocean Pines. Two ...
From $599 per night (USD)VRBO
From $338 per night (USD)VRBO
Ocean Pines-3 bdrm 2 bath home 8 minutes from Ocean City
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 bdrm 2 bath single family rancher, sleeps 6 with fireplace, all amenities, Internet/wifi. 7 miles (over 90th Street b ...
From $338 per night (USD)VRBO
From $325 per night (USD)VRBO
Updated! With new appliances and a new patio!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the ultimate vacation at the Sandcastle in Ocean Pines! Come stay at this 3-bedroom, 2-bath vacation home tha ...
From $325 per night (USD)VRBO
From $517 per night (USD)VRBO
Salty Air Serenity @ 728 Ocean Parkway in Ocean Pines, Maryland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Single Family Home with 3 bedrooms and 2.5 Baths + sunroom • Sleeps up to 8 comfortably • Driveway – accommodates 4+ ...
From $517 per night (USD)VRBO
From $189 per night (USD)VRBO
Pet friendly-Waterfront Home- Pools-Self Check-In- Beach Club Parking Included.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to 3 Clipper Ct in Ocean Pines charming 3-bedroom, 2-bathroom beach retreat, where relaxation and adventure come ...
From $189 per night (USD)VRBO
From $328 per night (USD)VRBO
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Beautifully furnished 3 bedroom, 2 bath, smoke-free condo on 9th fairway of Ocean Pines Golf Course as featured on Houzz ...
From $328 per night (USD)VRBO
From $506 per night (USD)VRBO
Summer Breeze - Waterfront Cottage For Rent
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summer Breeze Waterfront Vacation Home. During Summer Season we rent Saturday to Saturday Off Season short term weekend ...
From $506 per night (USD)VRBO
From $216 per night (USD)VRBO
Reasonably Priced Family- Friendly Home, Sleeps 7
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Ready for the 2022 Season, renovated in 2016. Need a little R&R or fun? Why not both? This property will give you just t ...
From $216 per night (USD)VRBO
From $744 per night (USD)VRBO
Scenic Water front secluded house with pier and view of the bay overlooking OC
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to the beach house at 241 Charleston Rd. in beautiful Ocean Pines, Maryland! Situated at the point of a natural ...
From $744 per night (USD)VRBO
From $268 per night (USD)VRBO
Beautiful Quiet Beach Home in the Pines Close to Everything
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a vacation home near Ocean City MD? You want to be minutes from all the fun and action? After a long day of ...
From $268 per night (USD)VRBO
From $623 per night (USD)VRBO
Gorgeous wired waterfront home with magnificent sunset views. Kayaks included.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This well-appointed home can sleep up to 12 people, including 6 in the fun bunk room. It has 4+ bedrooms and 4 full bat ...
From $623 per night (USD)VRBO
From $415 per night (USD)Expedia
Golf Course & Lakefront Retreat 4BR Sleeps 8 Gated Community Near Ocean City
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wake up to peaceful lake views and rolling fairways at this beautifully decorated 4-bedroom, 3-bath duplex located direc ...
From $415 per night (USD)Expedia
From $372 per night (USD)VRBO
Cozy Family Home Close to Ocean City
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
What you have been looking for... Whole home resort style stay with beautiful Ocean Pines Pools and scenery. Make your ...
From $372 per night (USD)VRBO
From $227 per night (USD)VRBO
Cozy Ocean Pines / Ocean City Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Affordable vacation getaway in South Gate Ocean Pines located minutes from Ocean City/MD. Quaint and cozy 3 bedrooms and ...
From $227 per night (USD)VRBO
From $427 per night (USD)VRBO
Recovery Room has a Private Pool & Hot Tub !! County License 1993. Sleeps Two
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summer County Short Term License Allows 2 Occupants. Long Term Off Season County License Allows 5 Occupants. ...
From $427 per night (USD)VRBO
From $330 per night (USD)VRBO
Adorable beach cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming beach cottage in Ocean Pines Community. Hardwood flooring, new furniture, new kitchen, new bathrooms and fresh ...
From $330 per night (USD)VRBO
From $589 per night (USD)VRBO
Million Dollar View! Waterfront oasis with Ocean City skyline view!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Waterfront home, handicap accessible. Fulfill the promise of a totally relaxing beach getaway in our home on the water. ...
From $589 per night (USD)VRBO
From $475 per night (USD)VRBO
Waterfront 5 Bedroom with Dock & Boat Ramp
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
SLEEPS 13. The Back Bay Bungalow House is located on a 2 acre peninsula with 3 other vacation bungalows that is across ...
From $475 per night (USD)VRBO
From $469 per night (USD)VRBO
Newly Renovated Home With Impressive Views Of The 7Th Green!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Ocean Pines Golf course home with impressive views of 7th green. Our large, comfortable 3 bedroom, 2.5 bath home has p ...
From $469 per night (USD)VRBO
From $161 per night (USD)Expedia
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
If you are looking for the perfect waterfront getaway this summer, this home is just the place for you! Located in Ocean ...
From $161 per night (USD)Expedia
From $1548 per night (USD)VRBO
Spacious waterfront/3 Levels/6 BR/5.5Ba/Elevator/4 Decks/Views! 5 stars
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Summer 2026 totally booked. Check back in mid-October 2026 for 2027 availability. Perfect for all ages (ele ...
From $1548 per night (USD)VRBO
From $268 per night (USD)Expedia
Snowbird Bay Cottage | Playground + Community Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Summary: Escape to Snowbird Bay Cottage, a charming getaway nestled in the peaceful White Horse Park community of Ocean ...
From $268 per night (USD)Expedia
From $368 per night (USD)VRBO
Canal Front Golf Retreat w/Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Waterfront 3BR/2BA townhome with stunning canal & golf course views in Ocean Pines. This pet-friendly retreat ...
From $368 per night (USD)VRBO
From $243 per night (USD)Expedia
🏖️Beautiful Home near OC & Assateague Park 🏖️
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to 21 Capetown, a charming 3 bedroom + loft / 2 bath unit in serene Ocean Pines! Just a short drive into Ocean C ...
From $243 per night (USD)Expedia
From $405 per night (USD)VRBO
57 Wood Duck Dr by Seaside Vacations & Sales
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $405 per night (USD)VRBO
From $281 per night (USD)Expedia
36 Rabbit Run Lane by Seaside Vacations & Sales
- 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 $281 per night (USD)Expedia
From $226 per night (USD)VRBO
Peace, Quiet and Serenity 12 miles from the beach
- Bedrooms:
- 2
- 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 $226 per night (USD)VRBO
From $353 per night (USD)Expedia
Coastal Chic Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: PERSONAL RESERVATION SPECIALIST AVAILABLE 24/7 FREE LINENS & TOWELS PROVIDED! Escape to our coastal chic ...
From $353 per night (USD)Expedia
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $1300 per night (USD)Expedia
Dolphins Chance - Waterfront Ocean Pines + Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Escape to your perfect retreat in Ocean Pines, MD! This beautiful waterfront home features 4 bedrooms and slee ...
From $1300 per night (USD)Expedia
From $372 per night (USD)VRBO
Cozy Home Minutes From Downtown Ocean City
- 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 $372 per night (USD)VRBO
From $620 per night (USD)Expedia
Waterfront Retreat with Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Escape to Qwack House, a beautiful 3BR/2BA waterfront, pet friendly, retreat in Ocean Pines. Perfect for famil ...
From $620 per night (USD)Expedia
From $435 per night (USD)VRBO
Incredible Bayfront Home with Amazing Sunsets! A warm home with lots of space
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A very warm home for three couples or a family of 6 or less. Three bedrooms and three and a half bathrooms. Nice open ...
From $435 per night (USD)VRBO
From $541 per night (USD)Expedia
Ocean Pines Chalet
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Nestled in the tranquil Ocean Pines, MD, Ocean Pines Chalet is a picturesque 4-bedroom, 3.5-bath haven exuding ...
From $541 per night (USD)Expedia
From $571 per night (USD)VRBO
4 bed 3 bath Living ,dining ,family rooms for large families with many children
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
🏡 Spacious Family-Friendly Getaway Near Bay & Beach – Beach Club Access + EV Charger! Perfect for large families or gr ...
From $571 per night (USD)VRBO
From $376 per night (USD)Expedia
Relaxing Family Getaway, Quiet Area Mins from OC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Kayaking, Marina, Pool On-Site | White Horse Park Community Effortlessly relax at this 2-bedroom, 1-bath home in Berlin ...
From $376 per night (USD)Expedia
From $341 per night (USD)VRBO
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Located in Ocean Pines, this neighborhood features quiet streets for your kids to ride bikes, playgrounds, parks, and co ...
From $341 per night (USD)VRBO
From $348 per night (USD)Expedia
White Horse Park-Spinnaker Lane 96 - Free WIFI,Pool,AC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Escape to a relaxing getaway in this spacious three bedroom home with an additional cozy den, located in a peaceful bays ...
From $348 per night (USD)Expedia
From $661 per night (USD)VRBO
3 Bedroom 2 Bath house featuring WiFi Smart TV Huge deck and patio Beach Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Detached 3 Bedroom 2 Bath Home featuring Central AC/Heat * WiFi * Fully Equipped Kitchen * Huge ...
From $661 per night (USD)VRBO
From $322 per night (USD)Expedia
Ocean Pines 2BR 1BA Cottage with Fire Pit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Escape to this stylish, pet-friendly A-frame cottage in a peaceful wooded setting. Perfect for up to 6 guests, ...
From $322 per night (USD)Expedia
From $1073 per night (USD)VRBO
Coastal Charm Oasis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our charming three-bedroom, two-bathroom vacation rental in beautiful Ocean Pines, MD. Perfectly situated just ...
From $1073 per night (USD)VRBO
From $459 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 $459 per night (USD)Expedia
From $1135 per night (USD)VRBO
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- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
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From $1135 per night (USD)VRBO
From $349 per night (USD)Expedia
Ocean Pines Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: This 3-bed, 2-bath home in Ocean Pines sleeps 8 and is ideal for a beach getaway. The spacious interior includ ...
From $349 per night (USD)Expedia
From $533 per night (USD)VRBO
Teal Bay Getaway- Waterfront, 2 Masters, Pet Friendly, 5+ Bedrooms, Sleeps 17+
- Bedrooms:
- 3
- 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 $533 per night (USD)VRBO
From $508 per night (USD)Expedia
Furnished Deck! Waterfront Ocean Pines Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
On-Site Bay Access | Patio w/ Al Fresco Dining Area | Great for Families Your bayside retreat awaits at this 2-bedroom + ...
From $508 per night (USD)Expedia
From $389 per night (USD)VRBO
8 Mi to Beach: Ocean Pines Home Near Marina & Golf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Ocean Pines Amenities (w/ On-Site Fees) | Deck w/ Dining Table | Gas Grill (Propane Provided) Go on a beach retreat to ...
From $389 per night (USD)VRBO
From $495 per night (USD)Expedia
Ocean Pines, 3 bedroom, sleeps 6, dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Relax and Unwind with the Whole Family! Welcome to your 1,500 sq. ft. home away from home—perfect for a pea ...
From $495 per night (USD)Expedia
From $610 per night (USD)VRBO
8 Mi to Ocean City: Warm & Cozy 3BR Family Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Dog Friendly w/ Fee | Spacious Sunroom | 9 Mi to Ocean City Boardwalk | 13 Mi to Assateague Island Enjoy the best of bo ...
From $610 per night (USD)VRBO
From $329 per night (USD)Expedia
Nicely Updated Three Bedroom Home in Ocean Pines
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: Nicely updated pet-friendly (2 dog max) home in the popular resort community of Ocean Pines, Maryland The S ...
From $329 per night (USD)Expedia
From $519 per night (USD)VRBO
Large Family Friendly Home in Ocean Pines, MD
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to this family friendly home in the quiet community of Ocean Pines, while remaining close to all the excitement o ...
From $519 per night (USD)VRBO
From $159 per night (USD)VRBO
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 $159 per night (USD)VRBO
From $452 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 $452 per night (USD)VRBO
From $534 per night (USD)Expedia
Coastal Colonial Charm located in Ocean Pines, MD by Karsons Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in a charming 2-story Colonial home in Ocean Pines, MD—a top-rated coastal community near Ocean City Beach and Assa ...
From $534 per night (USD)Expedia
From $378 per night (USD)VRBO
Rhapsody in Blue Beach Cottage in Ocean Pines OC MD w/ Beach Club Parking Pass
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the blue beach bubble. Located just 5 miles from Ocean City and 25 minutes from Assateague, our cottage is th ...
From $378 per night (USD)VRBO
From $215 per night (USD)Expedia
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 $215 per night (USD)Expedia
From $559 per night (USD)VRBO
OCMD Family Beach Retreat
- Bedrooms:
- 3
- 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 $559 per night (USD)VRBO
From $324 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 $324 per night (USD)Expedia
From $153 per night (USD)VRBO
Near it all OC beaches,Assateague island.Family-friendly white horse park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Home 2 bedroom-1 bathroom Laundry in unit Full eat in kitchen with crockpot, coffee maker, rice cooker, pots,pans,cups, ...
From $153 per night (USD)VRBO
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Poolside Fun & Beach Access in Ocean Pines!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
0.1 Mi to Yacht Club Marina | 10 Mi to Ocean City | Dogs Welcome w/ Fee Your next family retreat begins at this Ocean P ...
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From $589 per night (USD)VRBO
Pet-friendly home featuring a private fenced backyard for safe outdoor fun
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Dog-Friendly Coastal Getaway Near Ocean City, MD Bring your pups! This dog-friendly home welcomes up to 2 dogs with no ...
From $589 per night (USD)VRBO
From $381 per night (USD)Expedia
15% off 5 nights or more
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
We help make the most of your vacation by providing Free Admission seasonally to some of the area's top attractions each ...
From $381 per night (USD)Expedia
From $276 per night (USD)VRBO
10 minutes to Ocean/beaches, stylish, inviting home on a quiet tree-lined street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
"Experience modern, stylish living in this seamless open concept space with hardwood floors, panoramic windows, a vaulte ...
From $276 per night (USD)VRBO
From $413 per night (USD)Expedia
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
- Bedrooms:
- 2
- 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 $413 per night (USD)Expedia
From $429 per night (USD)VRBO
116 Pine Forest Drive by Seaside Vacations & Sales
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
You work hard all year long. Now is the time to slow down, and spend some hard earned, quality time with the ones who ma ...
From $429 per night (USD)VRBO
From $328 per night (USD)Expedia
Pet Friendly Home in Popular Ocean Pines
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Pet Friendly home in Ocean Pines community with tons of great amenities. The Space: Well-maintained PET FR ...
From $328 per night (USD)Expedia
From $495 per night (USD)VRBO
Charming Getaway with Boat Dock Minutes from Ocean City
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Charming Getaway with Boat Dock Minutes from Ocean City Welcome to 17 Driftwood Lane in beautiful Ocean Pines, Maryland. ...
From $495 per night (USD)VRBO
From $505 per night (USD)Expedia
Boat Dock! Waterfront Group Getaway in Ocean Pines
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Indulge in coastal relaxation with a stay at this scenic seaside vacation rental in Ocean Pines, MD. Perfect for large f ...
From $505 per night (USD)Expedia
From $412 per night (USD)VRBO
Ocean City Gateway: Modern 4BR/2.5BA home, dog friendly
- Bedrooms:
- 2
- 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 $412 per night (USD)VRBO
From $1299 per night (USD)Expedia
Ocean City MD waterfront rental with skyline views, canal access, bring your boat or jet ski!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to your Ocean City MD waterfront vacation rental with a private boat dock and beautiful Ocean City skyline views ...
From $1299 per night (USD)Expedia
From $549 per night (USD)VRBO
Large Direct Bayfront Home with Great Amenities
- Bedrooms:
- 4
- 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 $549 per night (USD)VRBO
From $540 per night (USD)Expedia
Beautiful Pines Home - Great for large families & close to all area attractions!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our Peaceful Pines Family Retreat located in the amenity rich community of Ocean Pines! Whether you are looki ...
From $540 per night (USD)Expedia