Ocean Pines Rentals
- From $264 per night (USD)
VRBO
Updated 3 Bedroom Ocean Pine Home with Screen Porch & Back Decking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
You will love the relaxing feeling you get as soon as you step foot into this beautiful Ocean Pines oasis. This lovely ...
From $264 per night (USD)VRBO
- From $361 per night (USD)
Expedia
Canalfront Ocean City Getaway w\/ Deck & Dock!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Look no further than this 3-bedroom, 2.5-bath vacation rental for your next Ocean City holiday. With the expansive outdo ...
From $361 per night (USD)Expedia
- From $205 per night (USD)
VRBO
Dog-Friendly Home with Deck, Fireplace, Central AC, Full Kitchen, & Fast WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Whimsical Willow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $205 per night (USD)VRBO
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Expedia
Beach Dreaming-Non Group Rentals-3 Bedrooms, 2 Bathrooms, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming home is conveniently situated directly on Ocean Parkway in the Ocean Pines community. You will immediately ...
Click For PricingExpedia
- From $260 per night (USD)
VRBO
Newly re-decorated
- 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 $260 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Dog-Friendly Ocean Pines Home w\/ Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Escape everyday stress with a trip to White Horse Park, a bayfront community that features ample family-friendly fun! Th ...
From $242 per night (USD)Expedia
- From $800 per night (USD)
VRBO
Waterfront oasis water sports of all kinds
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Ocean Pines property overlooking the Assawoman Bay. An oasis of birds, fish, turtles. There’s walking, biking path aroun ...
From $800 per night (USD)VRBO
- From $290 per night (USD)
Expedia
Home with central AC, gas fireplace, washer\/dryer, firepit, & shared pools
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Ocean Pines Fairway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $290 per night (USD)Expedia
- From $285 per night (USD)
VRBO
Golf course front home with deck, paid pool access & on-site dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Borderlinks 36 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $285 per night (USD)VRBO
- From $173 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 $173 per night (USD)Expedia
- From $212 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 $212 per night (USD)VRBO
- From $276 per night (USD)
Expedia
Private and pet-friendly in OP
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The homes amenities include a fully-equipped kitchen, high-speed internet and two work stations, 3 flat-screen Smart TV’ ...
From $276 per night (USD)Expedia
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Expedia
Two-story waterfront retreat with dock, fast WiFi & central AC
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Riverside Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $250 per night (USD)
Expedia
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 $250 per night (USD)Expedia
- From $350 per night (USD)
VRBO
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 $350 per night (USD)VRBO
- From $395 per night (USD)
Expedia
CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1\/2 BATHS, 2 KINGS, GOLF, RELAX...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This beautiful home is nestled on a canal located just off the Saint Martin's River in Ocean Pines Maryland. The quiet t ...
From $395 per night (USD)Expedia
- From $1067 per night (USD)
VRBO
Serene Sunrise & Shimmering Skyline. 5 Star Hosts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This West OC peninsula home is the most private home surrounded by canals, marshes and breathtaking views all day long. ...
From $1067 per night (USD)VRBO
- From $328 per night (USD)
VRBO
The Wild Horse Cottage *New Listing*
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
The entire house is yours to enjoy!!! The Wild Horse Cottage is located in Ocean Pines MD. The name pays homage to the ...
From $328 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Beautiful totally renovated 4 Bedroom Beach House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful four bedroom beach house that sleeps 12 . Screened in porch, barbecue, outside shower, beautiful outside seati ...
From $500 per night (USD)VRBO
- From $499 per night (USD)
VRBO
Ocean Pines Beach House
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 14
Welcome to our Ocean Pines home! Perfect for a large family or friends looking to spend time in Ocean City, but want to ...
From $499 per night (USD)VRBO
- From $741 per night (USD)
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 ...
From $741 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Waterfront townhome with deck, sunroom, amazing bay view & pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Marina Village 821 - Bayview Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $351 per night (USD)Expedia
- From $238 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 $238 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Sandy Pines Retreat - 3 Bedrooms, 2 Bathrooms, Sleeps 10-Non Group Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Located just minutes away from restaurants, shopping, Ocean City and the beach, this lovely 2 story home is the perfect ...
From $254 per night (USD)Expedia
- From $293 per night (USD)
VRBO
Reduced Rates Family Fun 4BR, 4BA, 5 Pools, fantastic back yard, Private Ocean Beach Club, Sleeps 12
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $293 per night (USD)VRBO
- From $261 per night (USD)
Expedia
Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy the cool breezes under the covered porch, grilling on the deck or try your hand at fishing in the back yard. You' ...
From $261 per night (USD)Expedia
- From $973 per night (USD)
VRBO
Amazing equestrian estate with luxury finishes & private pool
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 17
Brooklyn Meadows - The Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $973 per night (USD)VRBO
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Expedia
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 ...
Click For PricingExpedia
- Click For Pricing
Expedia
Eagles Nest At Watertown-3 Bedrooms, 2.5 Bathrooms, Sleeps 8, Non Group Rental
- Bedrooms:
- 3
- 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 ...
Click For PricingExpedia
- From $242 per night (USD)
Expedia
Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults loo ...
From $242 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Modern home with screened deck, central AC, washer\/dryer & well-equipped kitchen
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
A Watertown Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $365 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Charming House in a Beach Town Community!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Looking for a lovely space to unwind and relax after a busy day? Whether it is work or play, awake refreshed and ready f ...
From $295 per night (USD)Expedia
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Expedia
Waterfront Apartment with Boat Slip Minutes From Ocean City, MD Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Cute waterfront apartment with deck and private entrance that has access to boat slip and floating pier. Perfect for all ...
Click For PricingExpedia
- From $343 per night (USD)
Expedia
Capetown Gone Coastal - Non Group Rental, Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This nicely decorated 4 bedroom, 3 bathroom home has all the comforts of home. The fire pit was updated in 2023 with a l ...
From $343 per night (USD)Expedia
- From $228 per night (USD)
VRBO
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 ...
From $228 per night (USD)VRBO
- Click For Pricing
VRBO
Gorgeous Waterfront Vacation Home!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Stylishly decorated and impeccably maintained townhouse end unit direct waterfront to St. Martin's River. Two Master Su ...
Click For PricingVRBO
- Click For Pricing
VRBO
Endless Summer 😎
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom(s) Max Occupancy: 8 - 10 Persons A professionally managed community, this property offers exceptional value a ...
Click For PricingVRBO
- From $189 per night (USD)
Expedia
Fantastic gem near the beach with fast WiFi, shared pool, grill, central AC & WD
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Trinity Place Treasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $189 per night (USD)Expedia
- From $277 per night (USD)
VRBO
Eastern Shore Getaway with Screened Porch, WiFi & Access to 5 Pools & Beach Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Coral Shells Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $277 per night (USD)VRBO
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Expedia
Charming Eastern Shore Retreat w\/ Access to 5 Pools - Near Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Better Together Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For PricingExpedia
- From $375 per night (USD)
VRBO
Family friendly chalet, 5 mins. to pools, 12 mins. to beach - 4 beds, 2 baths
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Freshly updated chalet style home in the desirable Ocean Pines community. This lovely, tree-lined property can accommoda ...
From $375 per night (USD)VRBO
- From $170 per night (USD)
Expedia
Renovated Coastal Getaway with Pools, Golf, Tennis, Boat Launch & Beach Club
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Salty Sea Life Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $170 per night (USD)Expedia
- From $344 per night (USD)
VRBO
Large Townhouse Inside The GlenRiddle Golf Community
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
GlenRiddle is a luxury town home that features 4 bedroom, 3.5 baths with over 2800 ft.~ of living space. Features includ ...
From $344 per night (USD)VRBO
- From $334 per night (USD)
Expedia
Canal-side charmer with park views & deck + pool and sports court access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Peaceful Pintail Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $334 per night (USD)Expedia
- From $785 per night (USD)
VRBO
CAPE ISLE OF WIGHT BAY CANAL , BOAT DOCK. Dog Friendly, QUIET, CLEAN, ROOMY!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
** Due to the Pandemic, we have partnered with a CDC Certified Cleaning Company to professionally clean our homes before ...
From $785 per night (USD)VRBO
- From $183 per night (USD)
Expedia
Delightful House w\/ Fire Pit & Community Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover destination-defining attractions from the comfort of this 3-bedroom, 2-bathroom Ocean Pines vacation rental. Wh ...
From $183 per night (USD)Expedia
- From $239 per night (USD)
VRBO
Ocean Pines House w\/ Private Hot Tub 2 Mi to Golf!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A memorable stay awaits at this Ocean Pines home! Boasting a hot tub, large deck, and prime location, this 3-bed, 2-bath ...
From $239 per night (USD)VRBO
- From $143 per night (USD)
Expedia
Quaint Home w\/ Free WiFi, Full Kitchen, and a Furnished Sunroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Brooklyn Meadows - The Equestry Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $143 per night (USD)Expedia
- From $1672 per night (USD)
VRBO
Incredible equestrian estate & guest house with in-ground pool
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 22
Brooklyn Meadows - The Manor & Equestry Inn Our calendar is updated in real-time & our nightly rates are accurately di ...
From $1672 per night (USD)VRBO
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Expedia
BEST HOUSE in West Ocean City - GOLF & BEACH - Recent Upgrades - Sleeps 12
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Beautifully situated at the second shot of the 7th hole at Glen Riddle Golf course, a prestigious gated waterfront commu ...
Click For PricingExpedia
- From $354 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 $354 per night (USD)VRBO
- From $470 per night (USD)
VRBO
West OC Bayside Getaway W\/ Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
My place is in West Ocean City, a quick drive to the Outlets, Assateague, numerous restaurants, Frontier Town, and MUCH ...
From $470 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Manklin Creek Retreat-Waterfront,3 Bedrooms, 2.5 Bathrooms, Sleeps 8, Non Group Rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Granite kitchen counter tops and tile backsplash were installed in 2023. Make your vacation memories in this 3 bedroom, ...
From $263 per night (USD)VRBO
- From $255 per night (USD)
Expedia
Luxe Homey Get-Away Beach Cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Quiet and Private Spacious home, our guest have the privacy of a full kitchen, three large bedrooms, a large living room ...
From $255 per night (USD)Expedia
- From $262 per night (USD)
VRBO
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 $262 per night (USD)VRBO
- From $148 per night (USD)
Expedia
Canal-front dog-friendly home with private hot tub, pools, sports courts, views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Turtle Shores-22 Boston Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $148 per night (USD)Expedia
- From $191 per night (USD)
VRBO
Quaint dog-friendly 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 $191 per night (USD)VRBO
- Click For Pricing
VRBO
Ocean pines 4 bedroom
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newly renovated- very comfortable Sunroom and four bedrooms - new furniture thru out the home - 10 minute drive to ocean ...
Click For PricingVRBO
- From $215 per night (USD)
VRBO
Spacious golf course home, with screened in porch and beach access.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy your stay in this spacious and private modern home. Relax on the screened-in porch overlooking the golf course a ...
From $215 per night (USD)VRBO
- From $90 per night (USD)
Expedia
Cozy Cottage in Ocean PInes MD
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to our charming 3-bedroom, 1-bath cottage nestled in the beautiful community of Ocean Pines. This vacat ...
From $90 per night (USD)Expedia
- From $455 per night (USD)
VRBO
Waterfront Coastal Casual Home with Screened Deck + Boat Dock + Pet-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This charming canal-front house in West Ocean City sits between the beaches & boardwalk of Ocean City and the numerous a ...
From $455 per night (USD)VRBO
- From $135 per night (USD)
Expedia
Charming wooded home with shared pool, golf, sports courts, pier & marina
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Pines Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $135 per night (USD)Expedia
- From $417 per night (USD)
VRBO
Waterfront home with boat slip, furnished deck, grill, deck, & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Riverfront Refuge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $417 per night (USD)VRBO
- From $354 per night (USD)
Expedia
Skipjack Beach Cottage
- Bedrooms:
- 2
- Bathrooms:
- 0
- Sleeps:
- 4
FREE LINENS & TOWELS PROVIDED! Skipjack Beach Cottage is your perfect family beach retreat! Every inch of this home has ...
From $354 per night (USD)Expedia
- From $322 per night (USD)
VRBO
Ocean Pines Dog Friendly Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Indulge in the perfect family getaway at this pet-friendly Ocean Pines cottage, offering a warm welcome to your furry co ...
From $322 per night (USD)VRBO
- From $366 per night (USD)
Expedia
Waterfront Home with Boat Dock and Great Amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Space: Nicely updated waterfront home in the popular Ocean Pines community with three bedrooms and two-and-a-half ba ...
From $366 per night (USD)Expedia
- From $408 per night (USD)
VRBO
Ocean Pines House, New Construction! Route 90 Bridge to Ocean City
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Our Ocean Pines home is newly built. It has 4 bedrooms and 3.5 bathrooms. The large master bedroom is on the main floo ...
From $408 per night (USD)VRBO
- From $146 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 $146 per night (USD)Expedia
- From $329 per night (USD)
VRBO
Martinique Beach Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 0
- Sleeps:
- 8
PERSONAL RESERVATION SPECIALIST AVAILABLE 24/7 FREE LINENS & TOWELS PROVIDED! Welcome to our newly renovated beach hom ...
From $329 per night (USD)VRBO
- From $255 per night (USD)
VRBO
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 $255 per night (USD)VRBO
- From $411 per night (USD)
VRBO
Tree Top Bliss -Ocean Pines, Dog friendly sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: This is the perfect home to make some family vacation memories. This upscale and comfortable appointed, pet fri ...
From $411 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Dog-friendly, waterfront home with dock, fireplace, pools & great location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Whimsy Waterfront Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $139 per night (USD)Expedia
- From $181 per night (USD)
VRBO
Close to beach, pools & comes with beach pass!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: New listing! This 2 story colonial home is centrally located in the Ocean Pines Community. Safe, family friend ...
From $181 per night (USD)VRBO
- From $401 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 $401 per night (USD)Expedia
- From $412 per night (USD)
VRBO
☀️VIBRANT RETREAT⛱ 4 swimming pools, beach\/club, parks, tennis, pickleball, golf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Fun, clean, bright and happy! A stay here will leave you energized with a smile on your face! 1,400 sq ft. Single family ...
From $412 per night (USD)VRBO
- From $293 per night (USD)
VRBO
Newly Renovated 3BR 2BA, Modern Coastal Decor, Family Friendly, Quiet Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
You've found the perfect home for your family vacation! We have plenty of room for multiple families to enjoy time toget ...
From $293 per night (USD)VRBO
- From $400 per night (USD)
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 & ...
From $400 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Cozy Family Home in Ocean Pines
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 1
Relax with the family at this peaceful home. Outdoor scenery and pretty trails all around. The Ocean Pines community pr ...
From $150 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Home for the Entire Family
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Bring the whole family to this great place with lots of room for fun. Centrally located in Ocean Pines with plenty of r ...
From $399 per night (USD)VRBO
- From $229 per night (USD)
Expedia
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 $229 per night (USD)Expedia
- From $208 per night (USD)
VRBO
Ocean Pines-Borderlinks 48-AC, WIFI, Pool.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to The Borderlinks community in Ocean Pines. This charming three bedroom, two bathroom, three level townhouse of ...
From $208 per night (USD)VRBO
- From $554 per night (USD)
Expedia
Private Oasis - Private Pool, 4 Bedrooms, 2.5 baths, Sleeps 11, Non Group Rental
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
A perfect recipe for a great vacation is having good company in a great location! Welcome to the Private Oasis. A rare f ...
From $554 per night (USD)Expedia
- From $222 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 $222 per night (USD)VRBO
- From $312 per night (USD)
VRBO
The Cedar Cottage - 3 BR, 3 full bath, family-friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Relax and recharge at The Cedar Cottage in West Ocean City. Quiet, family-friendly neighborhood, yet only a couple mil ...
From $312 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Rhapsody in Blue Beach Cottage in Ocean Pines OC MD w\/ Beach Club Parking Pass
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $225 per night (USD)VRBO
- From $368 per night (USD)
Expedia
57 Wood Duck is a Waterfront Dream in the Heart of Ocean Pines
- Bedrooms:
- 3
- 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 $368 per night (USD)Expedia
- From $201 per night (USD)
VRBO
Cozy Coastal Cottage Ocean Pines
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New paint and flooring! Escape to a fun-filled getaway in this cozy coastal cottage nestled in the Ocean Pines communit ...
From $201 per night (USD)VRBO
- Click For Pricing
Expedia
On Beach Time, 3 Bedrooms, 2 Bathrooms, Sleeps 6, Non group Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New for the 2023 season! Make your vacation memories in this charming 3 bedroom, 2 bath home located in Ocean Pines. Thi ...
Click For PricingExpedia
- From $200 per night (USD)
VRBO
Cozy Pet Friendly Ocean Pines House Sleeps 6-8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Several updates, fenced in back yard with access ramp off a fully enclosed sunroom. A short walk to the park for several ...
From $200 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront dream with boat lift. Come sail way!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Gorgeous, fully remodeled home on the Isle of Wright Bay. Minutes from bustling Ocean City, Maryland, but nestled in the ...
Click For PricingExpedia
- From $83 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. 5 min walk to pool. Peace ...
From $83 per night (USD)VRBO
- From $215 per night (USD)
Expedia
This house is a 2 bedroom(s), 1 bathrooms, located in Ocean Pines, MD.
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Snowbird Bay Cottage is a charming and cozy vacation home located in the White Horse Park community of Ocean Pines, Mary ...
From $215 per night (USD)Expedia
- From $257 per night (USD)
VRBO
Reduced Family Rates 3BR, 2BA, 5 Pools, Back Yard, Private Ocean Beach Club, Sleeps 8, Free Tickets
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $257 per night (USD)VRBO
- From $403 per night (USD)
Expedia
Your Private Oasis on the Shore - Free Linens & Towels
- Bedrooms:
- 3
- Bathrooms:
- 0
- Sleeps:
- 8
Welcome to our breathtaking waterfront home, where luxury meets tranquility. Located on the serene shoreline, our home b ...
From $403 per night (USD)Expedia
- From $401 per night (USD)
VRBO
Casa Paloma at BorderLinks | 3BR Canal Front Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come stay at this recently updated Canal front 3BR 2BA townhome with the best water & golf course views! Downstairs host ...
From $401 per night (USD)VRBO
- From $317 per night (USD)
Expedia
VACATION RENTAL, 4 BEDROOM 3 BATH, DISCOUNT FOR 7 DAY RENTAL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Great vacation rental house with accommodations for up to 8 Total, includes children over 2 in Ocean Pines Resort, this ...
From $317 per night (USD)Expedia
- From $119 per night (USD)
VRBO
Dog-friendly coastal escape with yard and central AC - community amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Teal Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $119 per night (USD)VRBO
- From $204 per night (USD)
Expedia
🏖️Beautiful Home near OC & Assateague Park, 🏖️
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to 21 Capetown, a charming 3 bedroom + loft / 2 bath unit in serene Ocean Pines! Just a short drive into Ocean C ...
From $204 per night (USD)Expedia
- From $425 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 $425 per night (USD)VRBO
- Click For Pricing
Expedia
Captain's Quarters-Non Group Rental, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
New for the 2023 season! Enjoy sunny days and water views in this 2 story home located on the water in Ocean Pines. Five ...
Click For PricingExpedia