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The very best in Chincoteague Island & Ocean City Vacation Rentals

Relax, Rejuvenate, and Reconnect...

2023 VRMA Rental Management Company of the Year

Welcome To Seaside Vacations & Sales

You deserve the best on your vacation, and Seaside Vacations is here to make sure that is exactly what you get - the very best - Customer Service, Premiere Properties, and special touches such as Express Check-in and our Concierge Services. No matter your destination, whether it’s Chincoteague Island, Virginia or Ocean City, Maryland, we have the vacation rental for you.

Looking to get back to nature, reconnect with your family, and bond over majestic water views, and family-friendly activities? Check out Chincoteague Island, VA. Each of our Chincoteague Rentals provides an abundance of amenities and comfort no matter what size party you bring with you. Take an island boat tour, go fishing or crabbing, and let your taste buds rejoice with our local Chincoteague cuisine. Let us show you why Chincoteague Island has been voted ‘Best Small Beach Town”, and “Happiest Seaside Town”. You may never want to leave!

Need more city life or action-packed activities for your next vacation? Then Ocean City, MD is the destination for you and your family. Seaside Vacation provides the best selection of Ocean City Vacation Rentals, each with their own unique amenities that include; pool access, water and harbor views, boat slips, and even exercise gyms. Each vacation rental is located close to all of Ocean City’s major attractions. Take a stroll on our famous OCMD Boardwalk, catch some rays at the beach, or satisfy that retail itch with the shopping options that only Ocean City could provide.

Looking for a Pet Friendly Rental? We've got you covered. Our Chincoteague pet friendly vacation homes and condos allows you to bring the entire family with you...including Fido. It really isn’t a family vacation without them, right?!

When you book with us, you're not just reserving a place to lay your head at night - Seaside Vacations is here to provide the ultimate vacation getaway. Let us help you plan an amazing Chincoteague Island Vacation or Ocean City Vacation. We live here, and love nothing more than to share all we love about our heaven on earth with you!