Holiday rentals in Greenbackville

"Serendipity"- Houseboat Getaway

A "Tiny house on the water". Your home-base for exploring Delmarva! Serendipity is a vintage 36ft Holiday Mansion, nestled at Baywater Landing Marina in the stunning salt-water marshes of the Chincoteague Bay. From here, you are 35 minutes from Ocean City, MD, and 45 minutes from Chincoteague Island, VA. Serendipity 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!

Private Home in Quiet Beach Country setting

Take a wander off the beaten path for cozy, quiet setting where ALL the stars come out at night. Quick access to area beaches, parks, ocean & rivers for water activities of all sorts and great country backroads that are cycling friendly! Unplug & relax from the hectic city life. The screened back porch offers an outdoor dining area with shaded mornings & fantastic evening sunsets. Enjoy a firepit with smores. RATE based on number of Guests. Over 2BRs/4 guests will increase rates modestly.

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Sharkeys | Coastal Cabin-Water View + Sunset

10 minutes to the BEACH! Relax with the whole family at this peaceful 2-BR getaway featuring a full kitchen. Enjoy a bayside water view sunset from your covered deck. Linens, towels, & hand soap are provided. Located right next to our sister rentals, Roy’s Place & Nor’easter it’s perfect for friends or family traveling together who can stay close while enjoying their own space. Nestled on quiet North Main Street—just 6 miles from Assateague Beach and 1.5 miles from town.

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Cozy Barn Loft: Country Views & Central to Beaches

Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

Island View House

On Chincoteague Bay’s iconic Public Landing waterfront - 180 degree view of Assateague Island's horizon from Ocean City to Chincoteague. Perfect for sunrises, sunsets, sky gazing, bird watching and watersports. Sleeps 6, two bedrooms two baths, private dock, raised decks, and sunroom. 30 feet from the water. Public Landing has great swimming, boating, fishing and crabbing. Public pier boat ramp, and beach are within short walking distance and there are no fees.

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!

Sunset Dreams

Sunset Serenity: Walk to Pony Parade & Downtown The Space Experience the best of island living in this sun-drenched, two-story townhouse. Tucked away on a peaceful side road, our home offers a quiet escape while keeping you minutes from the heart of the action. Relax in the airy living room and enjoy the glow of the sunset after a long day at the beach—this is your perfect coastal basecamp.

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.