Holiday houses in Oyster Pond

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Top-rated holiday rentals in Oyster Pond

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Guest favourite

Home in Ocean City

4.94 out of 5 average rating, 219 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

15 – 22 Jan

$1,534 AUD total

Guest favourite

Condo in Ocean City

4.89 out of 5 average rating, 152 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

Pristine condo in North Ocean City with every amenity you can imagine welcomes guests over 21. Rare end unit offers more space than similar units. Two blocks from beach/park makes this the best location in town - fabulous sunset views and pool (Memorial thru Labor Day). 2 bedrooms and 2 stories offers spacious options for 6 guests to spread out. Full kitchen with everything, washer/dryer, central heat/air, Smart TV’s to access your streaming channels High Speed Internet and starter items

16 – 23 Nov

$949 AUD total

Guest favourite

Condo in Ocean Pines

4.96 out of 5 average rating, 108 reviews

Waterview Retreat

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

1 – 8 Nov

$1,925 AUD total

Guest favourite

Tiny home in Selbyville

4.98 out of 5 average rating, 211 reviews

Destination Location! Farm Animals, Tours, Beaches

Scratch staying in a tiny house off your bucket list! Escape the Ocean City crowds and slow life down at this Garden Hideaway. Situated on a ranch just minutes from the beach, this unique home has a barnyard of fuzzy animals ready to greet you each day. Curated to both inspire joy and create presence, enjoy a simple morning and sip coffee with Fonzie the alpaca, Charlotte the mini-pig and a front yard of silly goats sure to entertain. This is a magical stay that we're certain you'll love!

15 – 22 Oct

$1,608 AUD total

Guest favourite

Condo in Ocean City

4.99 out of 5 average rating, 101 reviews

Beautiful Renovated Ocean Front Condo 1b/1.5ba

Beautiful renovated ocean front condo. Get ready to relax in comfort and style! This large 836 sqft one 1b/1.5ba offers breath taking views of the ocean. You will be just steps away from the sand in one of the closest buildings to the beach. Enjoy your coffee or a different sunrise each day from your private balcony off the living room. Updated patio furniture with a cozy bench and high table with 2 chairs that bring a spectacular, completely unobstructed view of the beach and ocean.

11 – 18 Mar

$1,983 AUD total

Guest favourite

Condo in Ocean City

4.93 out of 5 average rating, 168 reviews

Coastal and Bright Oceanfront Condo

Relax and find your inner peace at our oceanfront condo. Enjoy breathtaking unobstructed ocean views from the private balcony. Wake up to a beautiful sunrise each morning and enjoy a peaceful moon-lit view in the evening. Our condo is filled with coastal and bright decor sure to make you feel right at home. Located in North Ocean City, you will find plenty of shops and restaurants within walking distance. Park your car, bury your feet in the sand, and forget about your worries.

31 Oct – 7 Nov

$1,912 AUD total

Guest favourite

Condo in Ocean City

4.91 out of 5 average rating, 239 reviews

Ocean-block 36th St. - Steps to the Beach!

Comfortable and affordable, our 1 bed/1 bath - 1st floor condo is in a prime OC Mid-Town location. Literally just steps from the building to the sand! Walking distance to me of OC's best restaurants, night life, amusements, convention center and more. **Summer Months check-ins on Monday & Friday ONLY from Memorial Day to Labor Day! Book Weeks or Mini-weeks. (Weeks: Fri to Fri, OR Mon to Mon) (Mini-Weeks: Mon to Fri, OR Fri to Mon)** *Other months check-in any night*

26 Dec – 2 Jan

$1,337 AUD total

Guest favourite

Guest suite in Berlin

4.99 out of 5 average rating, 149 reviews

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

16 – 23 Mar

$1,424 AUD total

Guest favourite

Apartment in Frankford

4.98 out of 5 average rating, 123 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

17 – 24 Oct

$1,661 AUD total

Superhost

Condo in Ocean City

4.88 out of 5 average rating, 106 reviews

Unit 11 on 41 St Ocean Side 50 steps to beach

Dominica Beach is a 2-story condo, close to the ocean on 41st Street Only 50 paces to the sand dunes and you'll have your toes in the sand! There are no streets to cross to get the beach. Complementary linen service based on the number of guests. Within walking distance of the Convention Center, restaurants, amusement parks, mini-golf, & more. You’ll love our place because of the ambiance. It is good for couples, solo adventurers, and families (with kids).

16 – 23 Nov

$1,092 AUD total

Guest favourite

Condo in Ocean City

4.9 out of 5 average rating, 141 reviews

Oceanside Oasis - Stylish Condo Steps to the Beach

Beautifully renovated one-bedroom condo just steps to the beach. Centrally located on 35th street our unit is close to shopping, restaurants, the Convention Center, and the boardwalk. Our private patio has a view of the beach and ocean, and the spacious kitchen has more than enough room to have some friends over for a meal. Located in Midtown, this area is full of nightlife, amazing restaurants, and a less crowded beach since there aren't any large hotels.

19 – 26 Nov

$1,344 AUD total

Guest favourite

Condo in Ocean City

4.99 out of 5 average rating, 175 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.

15 – 22 Nov

$1,666 AUD total