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 $326 per night (USD)
VRBO
116 Pine Forest Drive in Ocean Pines is a Fabulous Family Retreat, AND you can b
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 $326 per night (USD)
VRBO
$Cozy, dog-friendly home with pool & athletic court access, central AC, & W\/D$
From $391 per night (USD)
Expedia
Cozy, dog-friendly home with pool & athletic court access, central AC, & W\/D
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
The Red House at the Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $391 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Stunning golf course home with spectacular views
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Chelsea on the Green Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $446 per night (USD)
VRBO
$O.P. Yacht Club Townhome\/ 3 Br\/Pool \/Marina \/ golf$
From $342 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 $342 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Nice Three Bedroom Home in Popular Ocean Pines
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Space: Well-maintained vacation home in the popular Ocean Pines resort community. This home offers three bedrooms, ...
From $282 per night (USD)
VRBO
$Waterfront w\/Dock, Rooftop Terrace & 2 Kings$
From $630 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 $630 per night (USD)
Expedia
From $323 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 $323 per night (USD)
VRBO
From $411 per night (USD)
Expedia
O'Connell Home-Non Group Rental, 4 Bedrooms, 3 Bathrooms, Canal Front, Sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
New for the 2024 rental season.....renovated from floor to ceiling! This home has new flooring, ceiling fans, light fixt ...
From $411 per night (USD)
Expedia
$Sandyhook Road 106-AC, W\/D, Free WIFI$
From $196 per night (USD)
VRBO
Sandyhook Road 106-AC, W\/D, Free WIFI
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This terrific detached home is located in the quiet community of Ocean Pines. Enjoy the peace of your wooded getaway whi ...
From $196 per night (USD)
VRBO
$Waterfront Ocean Pines Vacation Home w\/ Boat Dock!$
From $307 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 $307 per night (USD)
Expedia
$Ocean City Gateway: Modern 4BR\/2.5BA home, dog friendly$
From $300 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 $300 per night (USD)
VRBO
From $286 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 $286 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Beautiful home with 2 living areas, deck, grill, pool, sports courts, skate park
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Ocean Pines Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $284 per night (USD)
VRBO
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Expedia
The Hollar's Beach House - 3 Bedrooms, 2 Baths, Sleeps 6, Non Group Rental-No Linens Provided
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Your family will enjoy this weekly rental property located an a wooded lot in Ocean Pines. The home offers an open floo ...
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Expedia
From $276 per night (USD)
VRBO
Family home tucked away on a quiet cul-de-sac in the serene community.
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to Bimini Beach Bungalow! The home includes a brand-new sofa & loveseat, with the rest of the home updated in ...
From $276 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Charming Ocean Pines Home - 9 Mi to Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Experience the charm of Ocean Pines in this beautifully appointed 2-bedroom, 1-bathroom vacation rental! The home is com ...
From $233 per night (USD)
Expedia
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VRBO
New waterfront townhome with views of OC skyline!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Brand new rental located in S. Ocean Pines. This waterfront property has the view of the OC skyline that is a ...
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VRBO
From $173 per night (USD)
Expedia
Cozy 3 Bedroom Beach Get-A-Way located in White Horse Park
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to this cozy 3 bedroom hidden beach gem located in the gated community of White Horse Park. This property boasts ...
From $173 per night (USD)
Expedia
From $343 per night (USD)
VRBO
LARGE WATERFRONT HOME IN QUIET NEIGHBORHOOD IN OCEAN PINES
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
***NEW LISTING! WATERFRONT DETACHED HOME IN SOUTH OCEAN PINES, BOAT DOCK AND LIFT AVAILABLE. ***** Large, beautiful wate ...
From $343 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Waterfront Retreat with Private Beach and Stunning Views on the St. Martin River
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This spacious waterfront home on the St. Martin River is a true gem! Enjoy fishing or crabbing from your private dock, o ...
From $469 per night (USD)
Expedia
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VRBO
Charming 3-bedroom house with AC and WiFi in Ocean Pines
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Two story home in a beach community, Ocean Pines, Berlin Md, just outside Ocean City Md. 4 miles to restaurants, outlet ...
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VRBO
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Expedia
Ocean Pines, Waterfront Oasis
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
About this space "Endless Summer" is on the canal at Moonshell Dr. Located on the St Martins River, North of the Rt 90 b ...
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Expedia
$510 Tee Time\n\n$
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VRBO
510 Tee Time\n\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your family will be close to everything when you stay at this centrally-located place. Right off ocean parkway next to t ...
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VRBO
$About 5 - 28 .\n$
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Expedia
About 5 - 28 .\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your family will be close to everything when you stay at this centrally-located home. We are 10-15 minutes to OC beaches ...
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Expedia
$Robin Hood Retreat\n\n$
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VRBO
Robin Hood Retreat\n\n
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Explore the Eastern Shore from this beautiful Ocean Pines home with 4 King Bdrms, 3 1/2 baths. Bring the whole family fo ...
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VRBO
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Expedia
Sunny Days
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Casual, spacious open floorplan, all on one floor with a huge back sun porch, nice front sun porch and ...
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Expedia
From $623 per night (USD)
VRBO
Family Tides, 6 Bedrooms, 3.5 Bathrooms, Sleeps 14
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
*Owner is offering a 10% discount to veterans and active military personnel. * Granite kitchen countertops, new kitchen ...
From $623 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Coastal Pines-3 Bedrooms, 2 Bathrooms, Sleeps 6-Non Group Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New for the 2024 season! Plan a summer escape to the serene and inviting "Coastal Pines," a delightful family-friendly v ...
From $233 per night (USD)
Expedia
From $140 per night (USD)
VRBO
Ocean Pines, MD Getaway - 10 minutes from beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Renovated Cape Cod that is in a quiet residential community and shaded by the many trees! This property includes 3 bed ...
From $140 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $159 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 $159 per night (USD)
VRBO
From $649 per night (USD)
VRBO
Beautiful brand new home in Ocean Pines
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy all Ocean Pines has to offer in this beautiful 4 bedroom, 2 ½ bath beach oasis. This home is perfect for families, ...
From $649 per night (USD)
VRBO
From $297 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 $297 per night (USD)
VRBO
From $293 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 w ...
From $293 per night (USD)
VRBO
From $548 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 $548 per night (USD)
VRBO
From $212 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 $212 per night (USD)
VRBO
From $440 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 $440 per night (USD)
VRBO
From $126 per night (USD)
Expedia
Luxe Homey Get-Away Beach Cove
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Quiet and Private Spacious home, our guest have the privacy of a full kitchen, three large bedrooms, a large living room ...
From $126 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Free boat dock, Is;e of Wight bay canal home. QUIET neighborhood, 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 $481 per night (USD)
VRBO
$Quaint Home w\/ Free WiFi, Full Kitchen, and a Furnished Sunroom$
From $147 per night (USD)
Expedia
Quaint Home w\/ Free WiFi, Full Kitchen, and a Furnished Sunroom
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Brooklyn Meadows - The Equestry Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $147 per night (USD)
Expedia
From $606 per night (USD)
VRBO
Incredible equestrian estate & guest house with in-ground pool
Bedrooms:
8
Bathrooms:
11
Sleeps:
22
Brooklyn Meadows - The Manor & Equestry Inn Our calendar is updated in real-time & our nightly rates are accurately di ...
From $606 per night (USD)
VRBO
From $341 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 $341 per night (USD)
Expedia
$Canal-Front Ocean City Getaway w\/ Deck & Dock!$
From $676 per night (USD)
VRBO
Canal-Front 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 $676 per night (USD)
VRBO
From $415 per night (USD)
Expedia
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 $415 per night (USD)
Expedia
From $347 per night (USD)
VRBO
GlenRiddle Townhouse #104
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
GlenRiddle #104 is a luxury town home that features 4 bedroom, 3.5 baths with over 2800 ft.~ of living space. Features i ...
From $347 per night (USD)
VRBO
$Waterfront getaway in a quiet neighborhood w\/ free WiFi, dock, & furnished deck$
From $235 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 $235 per night (USD)
Expedia
$Waterfront West Ocean City Home w\/ Skyline View!$
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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 ...
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VRBO
From $289 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 $289 per night (USD)
Expedia
From $297 per night (USD)
VRBO
Secluded Oasis with Expansive Outdoor Spaces, Bay Views, and Modern Amenities
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Silver Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $297 per night (USD)
VRBO
From $417 per night (USD)
VRBO
Charming 4-bedroom house with WiFi and AC in Ocean Pines
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Make yourself at home in this delightful 4-bedroom Ocean Pines retreat. 8 miles away from Ocean City. With 3 queen beds ...
From $417 per night (USD)
VRBO
From $291 per night (USD)
VRBO
NEWLY RENOVATED West OC Waterfront Beach Home; Large Deck & Private Boat Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Welcome to your home away from home in desirable West Ocean City. This house has been fully renovated in 2024 and contai ...
From $291 per night (USD)
VRBO
$New Quay Road 10338-West OC,AC,W\/D,Free WIFI$
From $260 per night (USD)
Expedia
New Quay Road 10338-West OC,AC,W\/D,Free WIFI
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
Welcome to your waterfront oasis in the serene neighborhood of Cape Isle of Wight, nestled at the end of the street in p ...
From $260 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Pet friendly Waterfront, Boat Dock, 3 bedrooms, 2 baths, quiet neighborhood.
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 ...
From $254 per night (USD)
VRBO
From $435 per night (USD)
VRBO
Updated Waterfront Home on Private Golf Resort & Pool - 4miles 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 $435 per night (USD)
VRBO
From $337 per night (USD)
VRBO
GlenRiddle Townhouse #102
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 $337 per night (USD)
VRBO
$West OC Bayside Getaway W\/ Private Pool$
From $112 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 $112 per night (USD)
VRBO
From $380 per night (USD)
VRBO
Waterfront Coastal Casual Home with Screened Deck + Boat Dock + Dog-Friendly!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
** 2025 Calendar Is Open! ** This charming canal-front house in West Ocean City sits between the beaches & boardwalk of ...
From $380 per night (USD)
VRBO
From $742 per night (USD)
Expedia
Ocean City Paradise, Large Outside Deck, Bar&Grill
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Escape to the most ideal vacation rental in all of West Ocean City with this beautiful waterfront charmer. Loca ...
From $742 per night (USD)
Expedia
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VRBO
Huge Home Situated on Golf Course; Close to Beach, Outlets, and Restaurants!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
****Important**** A Linen & Towel Package is included for all rentals between Memorial Day weekend and Labor Day weekend ...
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VRBO
$Waterfront wonder with screened porch, washer\/dryer, private boat dock & ramp$
From $382 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 $382 per night (USD)
Expedia
From $790 per night (USD)
VRBO
Golf course-adjacent condo with access to a pool, hot tub, & fitness room
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Glen Riddle Pleasant Colony 104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $790 per night (USD)
VRBO
From $228 per night (USD)
Expedia
New Quay Retreat, bring your Boat and fall in love with this West OC Beauty!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
You work hard all year long. When the time is right, you’re looking for just the right place to slow down, and spend som ...
From $228 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Cozy Private Apt 10 Minutes from Ocean city MD Beaches !
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Small cozy apartment including home amenities to relax to in the early mornings or late evenings. 10 min walk to Ocean ...
From $158 per night (USD)
VRBO
From $572 per night (USD)
Expedia
🏖️ Spectacular and Spacious Townhouse in Resort Community
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Spacious 4 Bedroom/3.5 Bath Townhouse has 3 large floors of living area in private gated community. Large family room w ...
From $572 per night (USD)
Expedia
From $583 per night (USD)
VRBO
Waterfront Home with OC Skyline Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to our stunning waterfront retreat with panoramic views of the Ocean City skyline! This large and luxurious home ...
From $583 per night (USD)
VRBO
From $310 per night (USD)
Expedia
BAYFRONT AT BRIGHTON
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully Updated, Dog-Friendly Home w/ a Large Deck, Private Dock, & A/C This open, bright cottage has been beautiful ...
From $310 per night (USD)
Expedia
From $542 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 $542 per night (USD)
VRBO
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 $299 per night (USD)
VRBO
5 minutes to Ocean City or Berlin - cozy 350' of waterfront living
Bedrooms:
2
Bathrooms:
4
Sleeps:
4
2021 Renovation !!! New bathroom!! New floors in the Florida room and new furniture. The pictures do not do this plac ...
From $299 per night (USD)
VRBO
From $1224 per night (USD)
Expedia
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)
Expedia

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Results: 270 Rentals