Fall Fun and Nearby Rentals in Ocean City, Maryland

After summer passes, Ocean City, MD has a fresh new feel. There’s an easygoing vibe and eclectic activities, so it’s easy to see why locals love living here. We recently previewed some of the biggest events coming to town for the fall. Now, we’re giving you the inside scoop on the best places to stay so you don’t miss a minute of the family fun.

Check your calendar and make plans for an autumn getaway. Book one of our recommended rentals below, or see the entire selection.

A Short Walk to Sunfest (September 19-22)

Celebrate the end of the summer season at Sunfest Weekend, Sept. 24-27 in Ocean City, MD.

Celebrate the end of the summer season at Sunfest, September 19th – 22nd in Ocean City, MD.

Sunfest is always one of the most popular fall events in Ocean City. This year will be no exception. The Inlet transforms into a vibrant celebration where the whole family can enjoy a lively mix of arts and crafts vendors, food vendors, kite displays and outstanding live music all day and night.

Make one of these rentals your Sunfest home base so you can walk there and back easily.

  • 509 Philadelphia Ave.—Bring family, friends, family of friends and your pets because this enormous single-family home sleeps 18! Enjoy six bedrooms, two bathrooms, a nice backyard, a white picket fence—the works! Located Downtown on 5th Street, you’re an easy walk from the Ocean City Boardwalk and Inlet area. Or feel free to hop on the bikes that come with the house. There’s always a great view of the main strip from your lovely front porch.
  • Bahia Vista I 104—The numbers add up for this beautiful bay front condo: Three bedrooms, two bathrooms, sleeps 10, four blocks from the Boardwalk. When you’re not out and about at Sunfest or strolling the shore, soak in the upscale décor or relax on your balcony along the marina. You have vast, beautiful views of the bay, which is mere steps away from your chair.
  • Bahia Vista I 408—You’ll feel right at home, yet still on vacation, in this luxurious four-bedroom, three-bathroom bay front condo. The interior is professionally decorated and exquisitely furnished, with high-end finishes in each room. The biggest draw for this property is the private, wrap-around balcony with picturesque views of the bay, which glows gorgeous reds, purples and pinks at sunset.

Keep the Cars Parked for Wine on the Beach (September27-28)

Wine lovers can enjoy themselves responsibly at the 25th Annual Wine on the Beach Festival.

Bottle of red? Bottle of white? Perhaps a little of both? Wine lovers can enjoy themselves responsibly at the 25th Annual Wine on the Beach Festival, or Wine Fest. Sample, savor and purchase concoctions from more than a dozen Maryland wineries and craft beers from local breweries at the Ocean City Inlet. Dance the day away to a variety of live music provided by some of the region’s favorite artists and bands. Book one of these rentals within walking distance of Wine Fest and you can put a cork in the idea of driving.

Enjoy extra windows, more natural lighting and a private gazebo balcony with ideal views of the beach and Boardwalk.
  • Belmont Towers 601—You can’t get much closer than this: a three-bedroom, three-bathroom oceanfront condo right on the Boardwalk in Downtown Ocean City. It’s a corner unit, which means extra windows, more natural lighting and a private gazebo balcony with ideal views of the beach and Boardwalk. (Yes, the people watching is still strong in September). There’s even a gym on-site if you want to get in a good workout before you get festive.
  • Belmont Towers 808—Keep your eye on Wine Fest throughout your stay in this spacious, two-bedroom, two-bathroom condo. Recently renovated, it’s a side unit with a south-facing balcony, promising ocean-to-bay views as well as a clear shot of the Inlet festival tents and Assateague Island in the distance.
  • Royal Palm Court 2—Ideal for small groups, this adorable one-bedroom, one-bathroom bayside condo is loaded with recent updates, including an upgraded kitchen and new TVs, furniture and flooring. Get to the Inlet easily with a short walk or a tram ride.

Don’t Miss a Moment of Endless Summer Cruisin’ (October10-13)

Cruisin' Ocean City Boardwalk
Cruisin’ Ocean City Boardwalk

If you haven’t been to Ocean City for this spectacular showcase of classic and custom cars, make this the year you bring your crew. It’s a gearhead utopia, with 2,000-plus vehicles on display in multiple parades and exhibitions at the Inlet and Ocean City Convention Center. Set your course for one of these downtown rentals near the Inlet and join fellow car enthusiasts for something new each day.


This Oceanfront condo that overlooks the Beach, Boardwalk, amusement rides & more! 
  • Belmont Towers 604—For parade time, the best seat in the house is literally in your house. Or your balcony, to be more specific. Stay at this three-bedroom, three-bathroom oceanfront unit on the Boardwalk and enjoy perfect views of the car parades from your balcony each morning. Want to get a closer look?You’re only a short walk to the Inlet.
  • Time-N-Tide 7—At the quiet end of the Boardwalk off 26th Street, this three-bedroom, two-bathroom condo puts you right in the heart of the parade route. Just slide open the balcony door and you’re overlooking Philadelphia Avenue and all the classic cars rolling their way through town.
  • South Beach 703—Consider this the Cadillac of condos—a luxurious three-bedroom, three-bathroom home in an oceanfront building on 7th Street in Downtown Ocean City, MD. This beauty comes fully loaded with free linens, an indoor pool and gym, and views of the ocean, bay and Boardwalk.Staying here lets you get to the Inlet in no time flat.

Find Your Home for Fall Events in Ocean City, Maryland

You can book a beach rental near these and other fall events at a great low rate!

Make plans to visit Ocean City, MD during its second season. You can book a beach rental near these and other fall events at a great low rate! Vantage reservation specialists are standing by to help. You can also browse all options and book direct at www.VantageOceanCity.com. Remember to book direct through Vantage so you get the lowest possible rates and the best possible selection.

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About Vantage

Founded in 2007, Vantage Vacation Rentals specializes in delivering exceptional experiences for both vacation property owners and their rental guests in popular Maryland destinations such as Ocean City, Annapolis and the Eastern Shore of the Chesapeake Bay, as well as the Delaware beaches and North Myrtle Beach, South Carolina. Vantage serves owners with extensive property marketing and promotion as well as comprehensive property management services to help maximize rental income opportunities. With over 550 managed properties, Vantage makes it easy for vacationing guests to find and reserve the perfect option—then enhances their stay with exclusive benefits and discounts. To learn more about Vantage Vacation Rentals, visit VantageOceanCity.com, EasternShoreVacations.com and VantageMB.com.