Places to stay near Assateague Island National Seashore

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

Jay's Retreat: dock, kayaks, EV charger, bikes

Welcome to Jay’s Retreat, a charming waterfront oasis nestled in scenic Oyster Bay. This beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood. End your days by the fire pit, soaking in the peaceful bay views and coastal breeze.

Adorable Beach Cottage Just Steps From Town & Bay

Escape to Wiggle Bay, a darling 1955 2 BR sunny cottage nestled in the heart of "one of the most beautiful, charming small towns in Virginia." Enjoy a bay breeze on the screened front porch--heaven! Perfectly located on a quiet street, just steps from local shops, a coffee house, and the waterfront park, where you can watch the boats, enjoy the sunset and feed the ducks. Just 2.3 mi to Assateague Seashore/Chincoteague Refuge. Ideal for a peaceful and convenient getaway!

"Jolly"- Houseboat Getaway

"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

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.

Baywatch North-Waterfront & Roaming Ponies

Lovely space! 2 bedroom/1 bath vacation efficiency, decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!

2 Bedroom Apartment

Centrally located between Chincoteague Island and Ocean City, MD. This pet friendly two bedroom apartment which offers laundry and a spacious kitchen is only steps away from Shad Landing state park and Public Landing. This ground level guesthouse apartment is located 200 feet from our main house is on an over 12 acre partially wooded parcel. Plenty of privacy and room for boat trailer parking.

Bayfront Modern Retreat • Dock, Kayaks, Views

Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginia’s Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.

Bayfront Cottage w/ Amazing Views

Whether you’re enjoying time by the firepit or sipping coffee on the couch, the views of Sinepuxent Bay and Assateague Island make this cottage the ideal spot for your next vacation. The cottage is located in a quiet neighborhood and is only a short drive from Assateague Island, the historic town of Berlin, and the Ocean City Boardwalk.