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

From $341 per night (USD)
VRBO
Dog-Friendly Getaway: 9 Mi to Ocean City Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Experience all Ocean Pines has to offer at this sunny vacation rental. Surrounded by lush greenery and gorgeous views, t ...
From $341 per night (USD)
VRBO
$9 Mi to Ocean City Beaches: Retreat w\/ Patio$
From $264 per night (USD)
Expedia
9 Mi to Ocean City Beaches: Retreat w\/ Patio
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
To secure a do-as-you-please getaway in Berlin, Maryland, be sure to book this charming 2-bedroom, 1-bathroom vacation r ...
From $264 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Coastal Cottage - Charm, Comfort and Spectacular Water Front near OC Beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Coastal Cottage -- Catch the breeze and magnificent open waterfront views from every room of this 3 bedroom, 2 bath rive ...
From $330 per night (USD)
VRBO
From $388 per night (USD)
VRBO
Pura Vida....Canal front beach cottage with private dock and sleeps 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Pura Vida is located in the north Ocean Pines community, just a 10-minute drive to Ocean City, Maryland. Situated in a ...
From $388 per night (USD)
VRBO
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
From $649 per night (USD)
Expedia
Ocean City Paradise, Large Outside Deck, Bar&Grill
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape to the most ideal vacation rental in all of West Ocean City with this beautiful waterfront charmer. Located direc ...
From $649 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Waterfront Marina Home on Private Golf Resort & Pool - 4 miles to OC Boardwalk
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy the waterfront views from the oversized windows in the living room or any of the 3 large bedrooms. Updated rooms, ...
From $408 per night (USD)
VRBO
From $372 per night (USD)
Expedia
A Wave From It All-Non Group Rental-Sleeps 6
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
New for 2025-hardwood flooring throughout the kitchen and living room. New ceiling fans throughout, new lighting, blacko ...
From $372 per night (USD)
Expedia
From $280 per night (USD)
VRBO
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 $280 per night (USD)
VRBO
$Huge Views Fam Vaca Home\/6Bedrooms\/5.5Baths\/4Decks\/Elevator\/KidFocus\/Top Reviews$
From $1496 per night (USD)
Expedia
Huge Views Fam Vaca Home\/6Bedrooms\/5.5Baths\/4Decks\/Elevator\/KidFocus\/Top Reviews
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
Hurry to book two peak summer weeks. Perfect for all ages (elevator!). One is the July Fourth week. Watch multip ...
From $1496 per night (USD)
Expedia
From $460 per night (USD)
VRBO
GlenRiddle Townhouse #104
Bedrooms:
8
Bathrooms:
4
Sleeps:
12
GlenRiddle is a luxury town home that features 4 bedroom, 3.5 baths with over 2800 ft.~ of living space. Glen Riddle off ...
From $460 per night (USD)
VRBO
From $389 per night (USD)
Expedia
This is it!! Rancher central to beaches, pools, golf, casino! Fenced yard, Deck.
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
A CUSTOM BUILT CONTEMPORARY RANCHER at the highest point in Ocean Pines centrally located between both Ocean City and As ...
From $389 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Beautifully Remodeled 3 BR, Ocean Pines, 6 miles to Ocean City
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Snuggly beds, Comfortable reclining sofas and an open floor plan with fully equipped kitchen. Cook together, be a part ...
From $265 per night (USD)
VRBO
From $481 per night (USD)
Expedia
3-bedroom Senior week friendly Beach home just 15 minutes from Ocean City .
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
In this lovely coastal town, you'll find our cozy three-bedroom 2 bath retreat nestled within the serene community of Oc ...
From $481 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Ocean City area. Pet friendly Waterfront, Dock, 3 bds, 2 baths, quiet.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Worcester County Rental License #1291. We are located on a West Ocean City canal with access to Assawoman Bay and the A ...
From $312 per night (USD)
VRBO
$Spacious 4 BEDROOM 3 1\/2 BATHROOM in Gated Resort Community$
From $615 per night (USD)
Expedia
Spacious 4 BEDROOM 3 1\/2 BATHROOM in Gated Resort Community
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Our 4 Bedroom/3.5 Bath Townhouse has 3 large floors of living area in private gated community with over 2800 ft of livin ...
From $615 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Family friendly close to OC, pool access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Abbey House is Located on a quiet cul de sac. This charming 3 bedroom home is a perfect getaway from the hustle and ...
From $327 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Superb Waterfront location on St. Martin River in Ocean Pines with 2 dock slips
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A true vacation oasis for the family that loves beach and boating! This gem is located right on the wide St. Martin Riv ...
From $475 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Waterfront 4 Bedroom with Dock & Boat Ramp
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
SLEEPS 11. The Back Bay Bungalow House is located on a 2 acre peninsula with 3 other vacation bungalows that is across ...
From $366 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $452 per night (USD)
VRBO
Quaint waterfront bungalow just minutes from the beaches of Ocean City, MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Looking for peace, relaxation, a breathtaking water view and, maybe, some kayaking, fishing or crabbing off your persona ...
From $452 per night (USD)
VRBO
$Large Townhouse in Gated Resort Community: 4 Bedrooms and 3 1\/2 Baths$
From $621 per night (USD)
Expedia
Large Townhouse in Gated Resort Community: 4 Bedrooms and 3 1\/2 Baths
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Spacious 4 Bedroom/3.5 Bath Townhouse has 3 floors of living area in private gated community. Hardwood Floors throughou ...
From $621 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Newly Renovated Home With Impressive Views Of The 7Th Green!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Ocean Pines Golf course home with impressive views of 7th green. Our large, comfortable 3 bedroom, 2.5 bath home has p ...
From $390 per night (USD)
VRBO
From $329 per night (USD)
Expedia
waterfront beach retreat with boat dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy this 3 bedroom home with beautiful water views from back deck & yard. This home has everything you need to enjoy ...
From $329 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Quaint, Dog-Friendly Berlin Vacation Home
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Enjoy your time away at our home at White Horse Park, a bayfront community with all of the amenities you need and just a ...
From $247 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Recovery Room offers a Private Pool and Hot Tub !!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
County Short Term License Recovery room is a wonderful 1000 square foot A Frame. With a great beachy feel, spacious d ...
From $369 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Huge Home Situated on Golf Course; Close to Beach, Outlets, and Restaurants!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
****Important**** Linens and towels are not provided with this rental. You will receive your check-in instructions with ...
From $328 per night (USD)
VRBO
From $310 per night (USD)
Expedia
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 $310 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Million Dollar View! Waterfront oasis with Ocean City skyline view!
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Waterfront home, handicap accessible. Fulfill the promise of a totally relaxing beach getaway in our home on the water. ...
From $440 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Relaxing Family Friendly Getaway in Ocean Pines
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
***During the Summer 2025 Season we will only accept bookings which are a minimum of 7 nights with Sunday Check-in and S ...
From $222 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Spacious, well maintained, 4br 3bath home overlooking Golf Course.
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This 4 Bedroom 3 bath home has space for everyone. Classic decor, overlooking the seventh green of Ocean Pines Golf and ...
From $448 per night (USD)
VRBO
$Golf course front\/Close to beach home-4 Bedrooms\/3 full baths - 8 separate beds$
From $412 per night (USD)
Expedia
Golf course front\/Close to beach home-4 Bedrooms\/3 full baths - 8 separate beds
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Located overlooking a lake on the 4th hole of River Run's world-class Gary Player-designed golf course. Guests of this r ...
From $412 per night (USD)
Expedia
From $334 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 $334 per night (USD)
VRBO
$Cozy Ocean Pines \/ Ocean City Cottage$
From $226 per night (USD)
Expedia
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 $226 per night (USD)
Expedia
From $523 per night (USD)
VRBO
Bowen's Landing-3 Bedroom, 3 Bathroom, Sleeps 6
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Kitchen and Sunroom are newly updated for the 2025 Season. New bar room doors were installed in 2024 so you can enjoy th ...
From $523 per night (USD)
VRBO
$House w\/ Screened-In Deck & Grill in Ocean Pines!$
From $368 per night (USD)
Expedia
House w\/ Screened-In Deck & Grill in Ocean Pines!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Go on a beach retreat to Ocean Pines and stay at this 3-bedroom, 2-bath vacation rental. This LGBTQ-friendly home boasts ...
From $368 per night (USD)
Expedia
From $604 per night (USD)
VRBO
Scenic Water front secluded house with pier and view of the bay overlooking OC
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Welcome to the beach house at 241 Charleston Rd. in beautiful Ocean Pines, Maryland! Situated at the point of a natural ...
From $604 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Canal-front home with fast WiFi, central ac, and private dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Dockside Daydreamin' Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $402 per night (USD)
Expedia
From $231 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 $231 per night (USD)
VRBO
From $519 per night (USD)
Expedia
Gorgeous wired waterfront home with magnificent sunset views. Kayaks included.
Bedrooms:
5
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 $519 per night (USD)
Expedia
$Waterfront West Ocean City Home w\/ Skyline View!$
From $372 per night (USD)
VRBO
Waterfront West Ocean City Home w\/ Skyline View!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Begin your blissful bayside getaway at this 3-bedroom, 2-bath vacation rental home in West Ocean City. This coastal cott ...
From $372 per night (USD)
VRBO
$Waterfront wonder with screened porch, washer\/dryer, private boat dock & ramp$
From $586 per night (USD)
Expedia
Waterfront wonder with screened porch, washer\/dryer, private boat dock & ramp
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Exeter Road Daydream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $586 per night (USD)
Expedia
From $1116 per night (USD)
VRBO
Beach house in ocean city only 4 m from the beach located in glen riddle golf
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Beautiful-house locatted in private community glen riddle golf , home is 4 minutes from the beach beach , amenities avai ...
From $1116 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Home Away From Home, pet friendly retreat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your Ocean Pines getaway. Off street parking for 4 cars stacked, and street parking if needed. Enter the home ...
From $397 per night (USD)
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 $497 per night (USD)
Expedia
Honu Blue-4 Bedrooms-3 Bathrooms-Sleeps 9-Non Group Rental
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
New dinning room table and chairs for the 2025 Season. New mattress on the bottom bunk of the pyramid bed plus new heat ...
From $497 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Spacious Two-Story Home with Full Kitchen, Balcony & Outdoor Fire Pit
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Seabreeze in Ocean Pines Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $461 per night (USD)
VRBO
$Waterfront getaway in a quiet neighborhood w\/ free WiFi, dock, & furnished deck$
From $221 per night (USD)
Expedia
Waterfront getaway in a quiet neighborhood w\/ free WiFi, dock, & furnished deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Canalside Comforts Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $221 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Beautiful Beach Cottage in Ocean Pines
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Open concept floor plan with lots of light and space for all of your guests in beautiful Ocean Pines. The property feat ...
From $264 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Coastal Waterfront Getaway- Pet Friendly - Pools- Golf-Sleeps 8- Self Check-In !
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our charming 3-bedroom, 2-bathroom beach retreat, where relaxation and adventure come together! Perfect for f ...
From $327 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Bayfront Home on Deep Water with dock, bay-view deck, WiFi & community pools
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Wood Duck Drive 4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $613 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Remodeled, Waterfront Home with Beautiful View, Dock, Large Deck - 1 Dog OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Harborview 17 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $355 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Canalside Home in North Ocean Pines with Dock, Screened Porch, WiFi & AC
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Ocean Parkway 289 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $365 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Ocean Pines Home with Central AC, Porch, Balcony, WiFi & Community Pool Access
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Beaconhill Road 68 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $282 per night (USD)
Expedia
$South Ocean Pines Home with Central AC, WiFi, W\/D & Community Pool Access$
From $377 per night (USD)
VRBO
South Ocean Pines Home with Central AC, WiFi, W\/D & Community Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Stop And Relax Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $377 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Dog-friendly home with wood-burning fireplace, central AC, WiFi, & pool access
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Seafarer 7 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $401 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Canalside Home in Ocean Pines with Large Deck, Canoes, Kayaks & Shared Pools
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Dove Lane 8 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $360 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Newly renovated Ocean Pines home with screened porch, AC, WiFi & on-site pools
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Sandyhook Rd 74 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $495 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Fairway to Heaven
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 $386 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Catch Me By The Sea
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
NEW in 2024: Three Season Sunroom, A/C unit & Vinyl Fence! Come relax & recharge in this newly updated and recently ren ...
From $351 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Summer Breeze - Waterfront Cottage For Rent
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Summer Breeze Waterfront Vacation Home. During Summer Season we rent Saturday to Saturday Off Season short term weekend ...
From $426 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 $207 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 $207 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Hook, Wine & Sinker- Waterfront, 3 Bedrooms, 2.5 Baths, Sleeps 10, Non group rental
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
1st and 3rd floor decks were completely updated with Trex in 2023. With stunning views of St. Martins River, invite the ...
From $642 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 $500 per night (USD)
Expedia
The Hingham House in OCMD!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Looking for the Luxury OCMD Vacation of your dreams? Look no further than The Hingham House in the private community of ...
From $500 per night (USD)
Expedia
From $306 per night (USD)
VRBO
OCEAN CITY MD BEACH HOUSE OCEAN PINES MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful single family beach home nestled in North Ocean Pines. Full kitchen, microwave, stove, dishwasher, pots and pa ...
From $306 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Fabulous Getaway in spacious 4BR 3.5 Bath Townhouse and a beautiful Golf Course.
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every ...
From $402 per night (USD)
Expedia
From $380 per night (USD)
VRBO
Salty Air Serenity @ 728 Ocean Parkway in Ocean Pines, Maryland
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
• Single Family Home with 3 bedrooms and 2.5 Baths + sunroom • Sleeps up to 8 comfortably • Driveway – accommodates 4+ ...
From $380 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
$Canal-Front Getaway w\/ Deck & Dock in Ocean City$
From $488 per night (USD)
Expedia
Canal-Front Getaway w\/ Deck & Dock in Ocean City
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 $488 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Updated! With new appliances and a new patio!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience the ultimate vacation at the Sandcastle in Ocean Pines! Come stay at this 3-bedroom, 2-bath vacation home tha ...
From $316 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Pool Access: Dog-Friendly Ocean Pines Home
Bedrooms:
1
Bathrooms:
3
Sleeps:
3
Escape everyday stress with a trip to White Horse Park, a bayfront community that features ample family-friendly fun! Th ...
From $282 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
Expedia
$Home with central AC, gas fireplace, washer\/dryer, firepit, & shared pools$
From $415 per night (USD)
Expedia
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)
Expedia
From $471 per night (USD)
VRBO
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)
VRBO
From $296 per night (USD)
Expedia
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)
Expedia
From $347 per night (USD)
VRBO
Private and pet-friendly, with game room and upgraded kitchen
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The homes amenities include a fully-equipped kitchen, high-speed internet and two work stations, 3 flat-screen Smart TV’ ...
From $347 per night (USD)
VRBO
From $368 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 $368 per night (USD)
Expedia
From $430 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 $430 per night (USD)
VRBO
$CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1\/2 BATHS, 2 KINGS, GOLF, RELAX...$
From $825 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 River in Ocean Pines Maryland. The quiet tow ...
From $825 per night (USD)
Expedia
From $1224 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 $1224 per night (USD)
VRBO
From $484 per night (USD)
Expedia
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 w ...
From $484 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Beautiful Beach House totally renovated 4 Bedroom 2 bath Pet friendly
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
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Expedia
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
Expedia
From $289 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 $289 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Sandy Pines Retreat - 3 Bedrooms, 2 Bathrooms, Sleeps 10-Non Group Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Located just minutes away from restaurants, shopping, Ocean City and the beach, this lovely 2 story home is the perfect ...
From $515 per night (USD)
Expedia
From $521 per night (USD)
VRBO
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)
VRBO
From $345 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
****Important**** A Linen & Towel Package is included for all rentals between Memorial Day weekend and Labor Day weekend ...
From $345 per night (USD)
Expedia
From $443 per night (USD)
VRBO
Amazing equestrian estate with luxury finishes & private pool
Bedrooms:
7
Bathrooms:
8
Sleeps:
17
Brooklyn Meadows - The Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $443 per night (USD)
VRBO
$Home on canal with views, pool\/tennis access, spacious deck & lovely interior$
From $437 per night (USD)
Expedia
Home on canal with views, pool\/tennis access, spacious deck & lovely interior
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Battersea on the Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $437 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 ...
Click For Pricing
VRBO
From $418 per night (USD)
Expedia
Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults loo ...
From $418 per night (USD)
Expedia
$Modern home with screened deck, central AC, washer\/dryer & well-equipped kitchen$
From $474 per night (USD)
VRBO
Modern home with screened deck, central AC, washer\/dryer & well-equipped kitchen
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
A Watertown Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $474 per night (USD)
VRBO
From $369 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 $369 per night (USD)
Expedia
From $480 per night (USD)
VRBO
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 $480 per night (USD)
VRBO
Click For Pricing
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
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 Pricing
VRBO
From $391 per night (USD)
Expedia
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)
Expedia

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