House holiday rentals in Maryland Beach

4.9 out of 5 average rating, 608 reviews

A charming tiny house features wooden shingles and a welcoming front door. It is framed by colorful flowers in a garden, enhancing the outdoor landscape. A sign above the door adds a personal touch, while large windows allow natural light to fill the space.

Home in Ocean View

Tiny House at Good Earth, near Bethany Beach

A custom 165 sq. ft. "Tiny House" located right between our theater and the garden dining area. True to the show "Tiny House Nation".. cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TV and internet in the unit. We have 2 on-site restuarants, market, theater, and parking. Our AIRBNB village consists of 2 tiny houses, 2 cottages, tent sites, a loft appartment, and more! Staying at Good Earth is more than a beach trip!

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, 121 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 two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.

4.97 out of 5 average rating, 133 reviews

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

A spacious outdoor deck features cozy seating arrangements and a coffee table, with ocean views visible beyond. Relaxing chairs are positioned around, while the sparkling coastline and beach access paths are displayed in the background.

4.92 out of 5 average rating, 13 reviews

NEW!OceanView-Pool-Sundeck-Bike-Theater-Game Room

Welcome to Your Elegant Oceanview Escape Home Experience the perfect blend of upscale comfort and family-friendly amenities in this spacious 5-bedroom retreat designed to host unforgettable getaways. Overlooking the sparkling coastline, steps from the beach, this home sleeps 16+ and offers everything you need to relax, recharge, and reconnect. Highlights • Breathtaking ocean views from multiple decks • Pool and sundeck (Pool closes Sept 29th 2025) • Arcade/game room • Outdoor movie deck!

A charming bayside home features a covered porch adorned with twinkle lights, creating a welcoming entry. The exterior showcases light-colored siding, large windows, and landscaped greenery, complemented by playful flamingo decorations on the front lawn.

4.97 out of 5 average rating, 106 reviews

Beach Oasis w/ King Suite + Outdoor Shower & Pool

Looking for a romantic weekend away? Planning a family vacation? Enjoy this entire bayside home in the quiet, coveted neighborhood of Montego Bay. This spacious 3 bed/2 bath retreat has it all!! Enjoy sunsets, steamed crabs, or coffee on the large porch picnic table or relax in the gliders with a cocktail under the twinkle lights! There is 2 car off-street parking & the community offers two public pools, tennis courts, trails, mini golf & is just a short walk to the beach & Northside Park!

A modern kitchen showcases a spacious island with seating for four. Elegant cabinetry and stainless-steel appliances complete the design. Natural light floods the area, highlighting the marble countertop and the decorative accessories. A large TV is mounted on the wall for convenience.

5 out of 5 average rating, 50 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

4.86 out of 5 average rating, 113 reviews

A modern kitchen is showcased with a dark refrigerator and sleek stainless steel appliances. A central island features a light granite countertop, while decorative shelves display dishware against a vibrant blue wall. Pendant lights illuminate the area, enhancing the functional layout.

Home in Ocean View

Pet Friendly | New EV Charger - New 100’ Fence!

NEW Fence JUST INSTALLED! 7 Hudson is a COMPLETELY renovated, three-bedroom, two full bathroom / family & pet friendly cottage that has everything you need for the perfect getaway. With 55” TV’s in every room. Located less than one mile to the town of Bethany Beach and within walking distance to restaurants, walking trails, parks, and other attractions. There are no CO producing appliances. Hardwired CO monitors on both floors. Thank you for your interest. (King bedroom on 1st & 2nd floor)

5 out of 5 average rating, 115 reviews

The exterior of a two-story house is framed by lush greenery and neatly arranged flower beds. A covered front porch with white railings invites guests, while the clean lawn extends towards the street. The sky above showcases a mix of clouds and blue.

Home in Berlin

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

4.99 out of 5 average rating, 102 reviews

A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.

Home in Ocean Pines

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

A spacious living area features large windows revealing expansive ocean views. A cozy seating arrangement is positioned near a modern fireplace. Light-colored walls and a neutral coffee table complement the calming atmosphere, while sliding doors provide access to a balcony with additional seating.

4.96 out of 5 average rating, 26 reviews

Direct Bay Front Epic Sunsets Rooftop Pool

Book 3 nights, get 1 night FREE stays thru March 10. inquire before booking This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED 2 ASSIGNED PARKING SPOTS! Absolutely stunning 3BR 2.5BA luxury bayfront penthouse condo sleeps 10 guest comfortably! Beautifully furnished and gorgeous sunset views. Building amenities include rooftop outdoor pool, elevator, and 200ft fishing pier. One block away from the beach and local restaurants!

4.85 out of 5 average rating, 198 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, DE

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.

A charming bungalow features dark blue siding and large front windows, framed by neatly trimmed bushes. A concrete walkway leads to the front door, and a well-maintained lawn surrounds the home. The sky is partly cloudy, adding to the inviting exterior.