Places to stay near Jolly Roger at the Pier

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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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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, 149 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
The front exterior of a charming two-story house is shown, featuring a pitched roof and light-colored siding. A bright blue door welcomes visitors. A white picket fence encloses the front yard, which is neatly landscaped with greenery and flowering plants.
Home in Ocean City
4.97 out of 5 average rating, 105 reviews

Dolores by the Sea- Family Groups ONLY

This recently remodeled 1950's house is walking distance to the beach, boardwalk, & fabulous restaurants. Tucked away from the hustle & bustle in a quiet neighborhood this cozy home is the perfect place to relax after a fun filled day at the beach. This home has 4 bedrooms & up to 7 beds. With a wheelchair ramp & a fenced in yard this house is perfect for family gatherings & making memories. Please note that due to neighborhood restrictions we cannot book to unrelated renters under 27 years old

Guest favourite
Condo in Ocean City
5.0 out of 5 average rating, 18 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 balcony setup features a dining table with four chairs, overlooking expansive views of the water and sky. The scene captures the coastal ambiance, with a distant glimpse of the town and boats along the shoreline.
Apartment in Ocean City
5.0 out of 5 average rating, 31 reviews

Assateague Views! Top Floor -Assateague House #505

Welcome to your perfect getaway at Assateague House, a beautifully appointed 2-bedroom, 2-bathroom condo with breathtaking southerly views of Assateague Island and a Bay Front Pool! This serene and spacious retreat is just steps from the Ocean City boardwalk, offering the best of both worlds—relaxing coastal scenery and easy access to shops, dining, and entertainment. ***Linens Not Included (Bedsheets, Pillowcases, Beach,Bath, Dish Towels) ***Linens can be arranged through a local linen company.

Superhost
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, 537 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
4.95 out of 5 average rating, 55 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!

Superhost
Condo in Ocean City
4.86 out of 5 average rating, 59 reviews

3BR Belmont Towers on Boardwalk ,Ocean & Bay Views

Enjoy PANORAMIC OCEAN & BAY VIEWS in one of Ocean City's NEWEST Buildings-Belmont Towers directly on BOARDWALK! Unbeatable location! ALL LINENS INCLUDED AND IN PLACE 24/7 Fast Customer Service Highlights Include: *huge balconies w/ direct access from living room & bedroom *outdoor pool *putting green *fitness center *washer/dryer *smart TVs in each bedroom *jetted tub in master bathroom *steps to Jolly Roger, Thrashers & many other restaurants *2 Free garage parking spaces

Guest favourite
A bright living area is furnished with a large sectional sofa adorned with turquoise cushions. A television is mounted on the wall, and a sliding glass door opens to a balcony with views of the ocean. A cozy electric fireplace adds warmth to the space.
Condo in Ocean City
4.86 out of 5 average rating, 37 reviews

Sunkissed Ocean Haven

Welcome to Sunkissed Ocean Haven, a stunning 3-bedroom, 3-bath beachfront retreat in Ocean City, MD! Fully renovated in 2023, this luxurious unit features en-suite bathrooms for all bedrooms, a spacious kitchen, and a wet bar. Enjoy panoramic ocean views from the primary bedroom and living room, breathtaking sunsets, and direct beach access. With a pool, sauna, fitness center, and parking garage, plus top restaurants and nightlife nearby, this prime location offers it all!

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
4.91 out of 5 average rating, 138 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
4.92 out of 5 average rating, 24 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*

Superhost
A welcoming living area is characterized by a turquoise wall and features a light blue couch paired with a colorful patterned chair. A white coffee table sits centrally, and a lamp provides soft illumination. Natural light enters through multiple windows, enhancing the airy feel.
Bungalow in Ocean City
4.5 out of 5 average rating, 52 reviews

Riptide Beach House

This three-bedroom retreat is full of charm and excitement. Step inside and be delighted. The first bedroom offers a comfortable double bed, perfect for a restful night. The second bedroom features a spacious king bed. In the third bedroom, you'll find two cozy double beds, ideal for sharing good times and relaxation. With everything you need to unwind and create lasting memories, your perfect getaway is right here. Let’s have some unforgettable moments together!

Guest favourite
Condo in Ocean City
4.83 out of 5 average rating, 121 reviews

Gated Renovated 2 Level Condo Downtown OC Bayview

Welcome to a Newly Renovated Two level condo in downtown Ocean City. Sunny 2 bedroom 2 bath with views of sunsets over the bay from a private balcony. Comes fully furnished and kitchen stocked with tons of gadgets. Smart TV’s in every bedroom and living area with Disney plus, YouTube tv, and Netflix. Feel Secure with gated building and parking. No car needed as restaurants, activities, boardwalk, jet ski rentals all within 2 blocks.

Popular amenities for holiday rentals near Jolly Roger at the Pier