Places to stay near Jolly Roger at the Pier

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.

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.

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 sunsets over the bay views from a private balcony. Comes fully furnished and kitchen stocked with tons of gadgets. Extra care taken with UV light sanitization after every rental. 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.

3 Level Townhouse in Downtown OC w/ 2 car garage

Experience the luxury at this 3-bedroom, 3-level townhome nestled in the heart of Downtown OC! Situated just blocks from the world-famous Boardwalk and beach, with an array of dining and shopping at your doorstep. No more fretting over parking, as this townhome boasts an attached 2-car garage. Open main level, gleaming stainless steel appliances, and exquisite granite countertops in the kitchen, create a culinary haven that will tantalize your senses and make every meal preparation a delight.

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 :)

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!

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.

Bayfront Escape w/Stunning Sunsets & Private Dock

Wake up to peaceful bay views and end your day with stunning sunsets at this beautiful bayfront apartment. Just a short walk to the beach and the OC boardwalk, you get the perfect mix of relaxation and convenience. Enjoy your morning coffee by the water, spend your day on the beach, enjoy the sunset, fish, or take a sunset cruise from the dock. Family vacation, couple's trip, or a weekend escape, this spot offers the perfect mix of comfort, and unforgettable scenery.

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.

Oceanfront Retreat • Balcony Views • Rooftop Pool

Oceanfront Luxury at Belmont Towers 404 — Balcony Views, Steps to the Beach Welcome to your oceanfront escape in the heart of Ocean City.Our unit offers a rare blend of luxury, comfort, and unbeatable Boardwalk access — all with sweeping views of the Atlantic right from your private balcony. Whether you’re here for family fun, a relaxing getaway, or a beach‑week adventure, this upscale 3‑bedroom condo gives you the perfect place to unwind.

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!

Luxurious Bay Front Condo

Escape to luxury at our bay-front condo, just 2 blocks from the beach. This tranquil retreat is perfect for families, offering stunning views and modern comforts. Enjoy nearby sandy shores, and unwind in a serene setting. Ideal for creating cherished memories. Optional boat slips available please message for details. (We do not rent to seniors for senior week)