View all of our Vacation Rentals | Choose your Destination

We offer a wide variety of Ocean City & Chincoteague Island vacation rentals in Maryland and Virginia. Below you will find different categories based on location or your desired amenities. You can choose rentals that are great for pets, have a pool or a view, central air conditioning  - we have something for everyone! Start exploring today, we can't wait to help you find the perfect Chincoteague rental.

Chincoteague Vacation Rentals

Ready for a Vacation you wont forget? Chincoteague Island has been voted "Best Small Beach Town" & "Happiest Seaside Town." We call it pure paradise! Seaside Vacations has so many beautiful Vacation Homes on the Island - whether youre looking for a Waterfront Dream Home or a Quaint Cottage, we have the perfect Home Base for your adventures. Located on the Eastern Shore of Virginia, Chincoteague is your escape from the large beach resorts. Experience Chincoteague Island and live like a Local in a Home rather than a Hotel. Enjoy walking to restaurants, shopping, or just spend the day on your private boat dock. We even have pet friendly rentals so you can bring everyone, including your pet. Seaside Vacations provides quality properties that will give you and your family a great stay during your Chincoteague Island Vacation. While you are here, you can enjoy Historic Downtown, take a Boat Tour, frolic on the Beach at Assateague National Seashore, and visit our Famous Wild Ponies at the Chincoteague Wildlife Refuge. Spend the day fishing in Chincoteague Bay or visiting our quaint Shops downtown. There is so much to do, you wont know where to begin! Call us today to book a vacation property for your family, a long weekend getaway, or a family reunion. Whatever your needs in a rental property may be, Seaside Vacations is here to assist you.

Ocean City Vacation Rentals

Voted One of the Top Beaches in the USA! Seaside Vacations offers the best in Ocean City Maryland Vacation Rentals from the Board Walk to the High Rise district. We have a selection of one to four bedroom condos, all with water views and great amenities. Vacation in luxury as you take in breathtaking ocean and bay views. Or stay in the heart of the action at one of our penthouse in the middle of Ocean City, MD. Select from a vacation rental with 2 to 4 bedrooms that can comfortable sleep up to 12 guests. Fully furnished vacation condos ready to make your vacation the best if can be. Close to the best parts of Ocean City, MD, our vacation rentals will make your stay relaxing and convenient for your entire family. Select from our Ocean City vacation rentals from below and book direct with us to save the service fees charged by the other vacation rental sites.

Captains Cove, VA

Captains Cove is a wonderful water privileged community nestled on the shores of Chincoteague Bay. Featuring a championship nine hole golf course, three swimming pools, fitness center, boat ramp & transient slips, full service dining and much more, every member of the family will find something to do here. Captains Cove is a short 20 minutes from Chincoteague and 40 minutes to Ocean City, MD. There is so much to explore will be back!

Pet Friendly Rentals

Here at Seaside Vacations, we are pet people, too, and realize that no Family Vacation is truly complete if our four-legged family members are left behind! Individual house descriptions indicate if dogs are allowed and if so, the number of dogs allowed. Premises that allow pets only allow friendly, housebroken, flea-free dogs that are on a veterinarian approved monthly flea/tick treatment and prevention program. Families that bring dogs are required to follow Seaside Vacations pet policies and pay non-refundable pet rent for each dog as applicable with their reservations.


Check out all of our vacation rentals with beautiful views of the water. Enjoy everything from a large home for family and friends to a luxurious romantic vacation getaway thats perfect for couples.


These vacation homes are directly on the water. Having a waterfront vacation rental offers convenient water access, beautiful views, and more privacy. Enjoy your next vacation with friends and family with a waterfront rental.

Pool/Pool Access

These vacation rental homes have access to a swimming pool. Being able to relax and swim in the pool just makes a vacation with your family and friends that much better!

All Vacation Rentals - MD & VA

The Best Selection of Vacation Rentals from Chincoteague to Ocean City! From Chincoteague, Virginia to Ocean City, Maryland, Seaside Vacations has an unmatched selection of Vacation Homes and Condos to suit your rental needs. From Luxury Oceanfront to serene Bay Views, and everything in between, make Seaside Vacations your one-stop source for your Vacation Rental needs. No one will work harder to provide you with your dream vacation! If youre looking for Navy Housing or other intermediate type stays for work around Wallops Island Flight Facility, give us a call - we can help!

Long Term Rentals

If you need Long Term Rentals in Chincoteague VA, Seaside Vacations has a large selection to choose from, and we frequently have access to rental homes that may not appear on our website. Seaside Vacations is the leader in Long Term Rentals within minutes of Wallops Island, Chincoteague, and Captains Cove. Be sure to give us a call if you do not see what you need available. Availability changes frequently in Long Term Rentals, so act quickly to secure the perfect rental for you.