House holiday rentals in Maryland Beach

A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 286 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!

A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.

4.93 out of 5 average rating, 148 reviews

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

A spacious living area features comfortable seating arrangements, including a large sectional sofa and recliners. A flat-screen television is positioned on an entertainment unit, and ample natural light is provided by multiple windows and a sliding door leading to the sunroom. Wooden flooring enhances the open atmosphere.

4.95 out of 5 average rating, 107 reviews

Spacious waterfront home & boat access!

Waterfront getaway, easy beach access (0.3 mile walk), pool, restaurants, and more. Linens & towels included! Bring your boat! Pier tie up available. Spacious 3 bedroom + bonus room with sleeping arrangements for 10(8 beds). This well-maintained home is close to dining, shopping, NorthsidePark & all the fun activities Ocean City has to offer. Beach chairs, toys, kayaks & paddleboard available. Fireworks from Northside Park can be viewed every Sunday summer night - right from the driveway!

5 out of 5 average rating, 63 reviews

New waterfront home on bay, quick walk to beach

Fresh remodeled beach house! Large outdoor canal front, fully fenced large back yard, quick walk to the beach. Well located, friendly residential neighborhood Located on quiet street with red light, quick walk to Gold Coast Mall, Green Turtle and Movie Theater. 3 bed/3 bath with multi-purpose bonus room with queen sleeper- use as a 4th bedroom / gaming room for kids/ office / 2nd family room for TV. All new TV's, appliances, and decor creates a modern experience in a classic beach house

An outdoor deck features a stylish seating area with a sofa and a coffee table, complemented by an umbrella providing shade. A dining table is visible, suitable for gatherings. The view includes a calm canal with houses along the opposite shore.

4.95 out of 5 average rating, 75 reviews

Tranquil Water View! Kayaks & SUP Boards Included!

Welcome to LIVIN ON BEACH TIME! Enjoy this Cozy Peaceful Retreat this year! Our updated home has all you need for a great time! Loaded with all amenities you need to make your stay comfy & fun. Our deck overlooks the gorgeous canal. Enjoy stunning sunsets . We have everything on hand for happy outings at the beach or fun on the water. RELAX... You're at the Beach! BECAUSE THIS IS A SEASONAL LISTING, MAY 23 - SEPT 7 2025, REQUIRE CHECKIN/CHECKOUTS ON SATURDAYS AND SUNDAYS ONLY.

The exterior of a modern house is presented at dusk, featuring a welcoming porch with multiple seating areas. Illuminated windows reflect warm light, while a lamp post adds ambiance. A tidy driveway leads up to the home, framed by well-maintained landscaping.

5 out of 5 average rating, 63 reviews

Upscale Family Home in OC, Community Pool, Grill

Unwind in North OC at the Nautical Vibes House! • A new, stylish single-family home designed to make your stay comfortable and memorable • Equipped with EV Charger, full kitchen, 2 Smart TVs with Youtube TV, washer/dryer, and outdoor shower • In a quiet neighborhood, but still close to restaurants, bars & shopping. Just under a mile to the beach & Northside Park • Has 2 community pools, tennis courts & putt-putt course (between Memorial Day/Labor Day only, keycard provided)

4.98 out of 5 average rating, 104 reviews

The backyard features a well-maintained putting green, with white flags marking the holes. A spacious home with a covered patio and landscaped garden is visible in the background, surrounded by lush greenery and trees.

Home in Berlin

Assateague, Golf, Ocean City, all Within Minutes!

Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

A vibrant pot of red flowers is positioned in the foreground, with a wooden deck leading to a clear blue pool in the background. The pool area features a white fence and steps, surrounded by greenery and a cloudy sky above.

4.98 out of 5 average rating, 159 reviews

Stunning Bayview Home with Own Private Pool

This home can be occupied by a max of 12 adults with a total of 15 including children. Come relax in this gorgeous bay view single-family home in the lovely Caine's Woods neighborhood of Ocean City, adjacent to Fenwick Island. Imagine lazy days spent on the beach followed by a dip in the pool outside the kitchen door! GUESTS USE POOL AT THEIR OWN RISK! The pool is open from May 1- September 30. Obviously we can’t have it open during cold temperatures!

4.86 out of 5 average rating, 209 reviews

The cottage exterior is seen with a large deck featuring white railings and a blue and white striped awning. A set of outdoor furniture is arranged on the deck, and steps lead down to a grassy area. The well-maintained, light-colored siding complements the serene environment.

Home in Fenwick Island

Hall Cottage, Fenwick Island, Delaware

Charming, updated cottage. Wifi and space to work. Located between Bethany Beach, DE and Ocean City, MD, Fenwick is known as 'The Quiet Resort.' Two blocks to the beach. The cottage is the perfect size for a couple or small family. Sitting on a lovely, quiet block, between the ocean and the bay, the cottage is a quick walk to fine dining, pubs and shopping. The cottage comes with two beach chairs and an umbrella, an outdoor shower, and a beach parking pass.

5 out of 5 average rating, 21 reviews

High Tide @ Lighthouse Bay

Welcome to High Tide @ Lighthouse Bay, a spacious 4-bedroom, 3+bath townhome just steps from the beach in Ocean City, MD! With two living spaces, a beautiful kitchen, and a loft area for kids with a bunk bed, this home is perfect for large families or group retreats. Most bedrooms offer private access to patios, and you’ll enjoy breathtaking sunsets and the convenience of being within walking distance to the beach, restaurants, and nightlife!

5 out of 5 average rating, 124 reviews

A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.

Home in Newark

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.