Waterfront holiday rentals in Assateague Island

Pony Pines!Your Waterfront Getaway Cottage Awaits!

Imagine a quiet retreat on the water where the sunsets are magnificent, and wildlife such as geese, raccoons, deer, owls, and egrits are to be experience in the backyard. Pony Pines offers a firepit, a master bedroom with a jacuzzi tub, and a clawfoot tub on the main floor. We have 2 Kayaks for your use on the canal, and a storage shed with some of the beach accessories you may need for your days at the Ocean. Linens are provided! Relax with your whole family at this peaceful, Happy Place.

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

Ocean Pines Getaway

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

"Serendipity"- Houseboat Getaway

Serendipity is docked at an active marina with watermen and pleasure cruisers, nestled off the Chincoteague Bay. Sleeps up to 4 adults craving coastal tranquility. From the boat, the Chincoteague Bay is in view and ready to be explored. Enjoy a full spectrum of awe-inspiring coastal wetlands, historic downtown areas, and beaches all within a few minutes' drive. Truly, the perfect setting for a much deserved recharge. 35 Minutes from Ocean City, Assateague Is, and Chincoteague Is.

Mosaic Life Escapes -Bayfront Million Dollar Views

At Mosaic Life Escapes the BAYFRONT is our back yard! Safe gated community home. Water access for paddle boards & kayaks. Community fishing/crabbing pier 2 pools 3 ponds arcade room, playgrounds, paddle boats. 2 bd home w/a million dollar view. Minutes from Ocean City, Assateague Island & Casino. WiFi + 3 smart TVs We have implemented additional sanitizing procedures between guest stays to ensure a clean house! Perfect for a family or romantic get away!

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Sunset Haven Downtown

Broadband WIFI newly installed and dependable! This special place is located in the heart of historic downtown Chincoteague above a wine shop/jewelry boutique. Your backyard is a waterfront park with our famous Love Chairs! Watch the sunset from your waterfront window or deck. Walk to shopping, restaurants, and more! An apartment with old time charm and new polished adds to feel as modern as needed! Onsite Laundry- Linens provided

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.