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Places to stay near Jolly Roger at the Pier

Book unique holiday rentals, homes and more on Airbnb

Top-rated holiday rentals near Jolly Roger at the Pier

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Condo in Ocean City
5 out of 5 average rating, 15 reviews

Downtown Condo, Parking, Walk to Beach & Boardwalk

Modern 2BR/2BA downtown Ocean City condo with bay view, balcony, elevator, pool, and parking. Sleeps 6 with 1 king and 2 queen beds. Walk about 1,000 ft to the inlet beach, boardwalk, rides, pier, dining, festivals, and downtown events. Enjoy a full kitchen, dishwasher, washer/dryer, smart TVs, WiFi, linens, bath towels, beach towels, chairs, umbrella, and cooler. Includes 1 assigned parking space plus 1 shared first-come space with passes. Perfect for families, couples & event-goers year-round.

Top Guest favourite
A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.
Condo in Ocean City
4.99 out of 5 average rating, 138 reviews

Gorgeous Beachfront! King Bed, Direct Ocean View!

Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

Top Guest favourite
Condo in Ocean City
5 out of 5 average rating, 13 reviews

BeachBox IV • Walk to Boardwalk • Bayside Pool

Just looking? ❤️ Add us to your Wishlist. Questions? 💬 Message for a quick reply. Beautifully decorated corner unit, just 2 blocks to the Boardwalk, beach and all of OC's downtown attractions. Guests rave that it's impeccably clean, well-stocked, & family-friendly, with thoughtful touches throughout. Relax by the bayside pool or enjoy coffee on the open balcony. Enjoy free parking, smooth check-in, & friendly hosts. Whether your first visit or a repeat stay, this cozy retreat feels like home.

Superhost
A row of newly built townhouses is displayed, showcasing vibrant blue siding and white trim. Each unit features a small patio deck and a private garage. The rooftops are accented with gables, framing the expansive sky above. Paved pathways and landscaping can be seen at the front.
Home in Ocean City
4.8 out of 5 average rating, 35 reviews

Gina’s Square Beach Homes Unit C

Come enjoy our newly built townhouses in the heart of downtown Ocean City. Family friendly, spacious, 2 patio decks, private 2 car garage. Full size kitchen and dining room area. 2 bedroom, 2 bathrooms. Master bedroom with a Queen size bed and TV. Secondary room with 1 twin, pyramid bunk bed with twin and Full bed. Queen size sofa bed. Major appliances including washer/dryer. Free WiFi provided. 5 minute walk to the boardwalk and seconds away from the Ocean gateway bridge, perfect for fishing.

Superhost
The exterior of a multi-level townhome is shown, featuring a mix of beige and blue siding. Multiple balconies with white railings are visible, along with landscaped shrubs and trees. The street in front is paved, with a clear view of the surrounding neighborhood.
Townhouse in Ocean City
4.76 out of 5 average rating, 54 reviews

Steps to OC boardwalk with partial bay views

Big & beautiful bayside townhome in downtown Ocean City. Enjoy 3 floors, 3BRs (sleeps 8), 3.5 baths & a 2-car garage. Boasts 2300 square feet & an open concept floor plan, perfect for spreading out & relaxing. Located around the corner from the bay, boardwalk, beach, fishing, park, skateboard park & the outdoor bayside restaurant, "De Lazy Lizard," perfect to watch stunning sunsets. Private balconies on all levels to relax on lazy evenings or enjoy a cup of coffee to start the day off right.

Top Guest favourite
Bungalow in Ocean City
4.88 out of 5 average rating, 145 reviews

🌅🎢Bungalow 1 block to boardwalk on 4th st!

Private yard 🌞 Outdoor shower 🚿 Premium cable/ NFL RedZone/ MLB ticket! 🎟️ Beach 🚲 s Beach chairs and 🏖️! Come enjoy our 1940s bungalow, just one block from the boardwalk, one block from the bay, and brand new downtown park. Our cozy retreat offers a unique blend of vintage appeal and modern amenities. Enjoy the provided beach chairs and umbrella, afternoons in the yard, rinse off under the outdoor shower after the beach, cook in our fully stocked kitchen, or explore town on a bike.

Top Guest favourite
The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.
Townhouse in Ocean City
4.97 out of 5 average rating, 525 reviews

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Top Guest favourite
A modern living area is featured with a comfortable sectional sofa accented by colorful throw pillows. A wooden coffee table sits centrally on an area rug. The large window provides a view of the waterfront, with sliding glass doors leading to a balcony.
Condo in Ocean City
4.96 out of 5 average rating, 49 reviews

Downtown-Pool-Boardwalk-Bay Views-Marina-Boat Slip

Luxury waterfront condo conveniently located two blocks from the world famous attractions on the Ocean City boardwalk. A short walk will have you sitting on the beach in minutes. Afterwards, take a dip in the community pool. Be sure to watch for the charter boats as they bring in their daily catch to the marina below. Enjoy happy hour on your private balcony overlooking beautiful bay sunset views. Whatever you're looking to do, our unit is perfectly situated in the heart of it all!

Top Guest favourite
Vibrant orange and yellow lilies are in full bloom, positioned in the foreground along a pathway. The path leads towards a waterfront area, with chairs visible in the background. A clear sky and soft sunlight enhance the peaceful ambiance of the setting.
Townhouse in Ocean City
4.96 out of 5 average rating, 48 reviews

Bayfront - Walk to Beach & Boardwalk - King Bed

Welcome to our Home Beach Resort! Just a 5-minute walk to Ocean City Beach, boardwalk, bars, restaurants, and amusement parks. 🌅 Bayfront Views – Enjoy stunning sunrises from the master bedroom and sunsets on the bay. 🏡 Comfort & Convenience – Fully furnished home with a private gated boardwalk. 🎣 Outdoor Fun – Fish and crab right in front of the house! ☕ Modern Amenities – Fully equipped kitchen, Keurig coffee maker, WiFi-6. Book now for the ultimate Ocean City getaway!

Guest favourite
Home in Berlin
4.97 out of 5 average rating, 35 reviews

White Marlin Cottage>HOT TUB<

Property Is Located Along RT 611 Within 3 miles to Ocean City Beach and 7 miles to Assategue Island Beach also within 3 miles of a Marina at the Bay to drop your boat in the water to enjoy fishing,crabing,swimming,skiing etc... White Marlin Cottage has a back yard patio with string lights , hot tub, grills, camp fire pit , a cast iron sink to clean your fish ,A sand box for children a yard where children can enjoy games and driveway space to park your boats etc...

Top Guest favourite
The open concept living area combines a kitchen, dining space, and lounging area, featuring light-toned cabinetry and modern appliances. A round dining table with two stools is positioned near a window, while a cozy couch and media console are arranged for comfort and convenience.
Apartment in Ocean City
4.92 out of 5 average rating, 125 reviews

Bright and Airy Oceanside Condo

Wake up to stunning ocean sunrises from your private balcony and enjoy bay sunsets just outside your front door. This oceanside condo in midtown Ocean City, MD is steps from the beach!! Beachside with no street to cross. Park your car for free in our covered lot. Enjoy a walkable location near top restaurants, bars, nightlife, and attractions like Seacrets, Fager’s Island, Macky’s, breakfast at barn 34 and mini golf. Ideal for a convenient Ocean City beach vacation.

Guest favourite
A spacious living area is furnished with a large sectional sofa and two armchairs, creating a comfortable seating arrangement. A coffee table sits in the center, while a flat-screen TV is mounted on the wall. Large sliding glass doors open to a balcony with ocean views.
Condo in Ocean City
4.91 out of 5 average rating, 22 reviews

Fabulous Boardwalk Oceanfront w/ Pool

Beautiful 3 bedroom, 3 bathroom, 3rd floor oceanfront condo on the Ocean City Boardwalk! This unit sleeps up to 11 guests and offers free Wi-Fi, HDTVs, large balcony that overlooks the boardwalk, gourmet kitchen, beach chairs and umbrella in locker. New 75" Samsung TV in Living room, *Linens are not provided, but can be added to your reservation for a fee **NO RENTALS TO ANY GROUPS UNDER THE AGE OF 25** Families with children are welcome! *No Smoking, No Pets*

Popular amenities for holiday rentals near Jolly Roger at the Pier