Holiday rentals in Greenbackville

Serene Waterfront Metompkin Retreat - Entire Home

Discover serenity at the ultimate retreat on Virginia's Eastern Shore at our waterfront oasis. Indulge in sweeping panoramic views of the tranquil waters that stretch as far as the eye can see. Nature enthusiasts will delight in the abundance of birdlife, making it a true birdwatcher's paradise. Whether sipping coffee on the private deck at sunrise or enjoying a glass of wine while watching the sunset paint the sky, every moment here is a picture-perfect postcard. A truly unforgettable getaway.

Waterfront-Views from all rooms-CI bay sunset

Leighward Landing has everything you need for a fabulous vacation on Chincoteague Island. Located on South Main St. only 2 miles away from downtown shops and 4 miles to the entrance of Assateague beach state park. Our waterfacing beach house is perfect for larger families because of it's wonderful open floor plan and separate sleeping quarters on the second level. Enjoy gorgeous waterveiws from 6 of the 11 rooms. Newly renovated and incredibly well equiped-book early so you don't miss out!

Dog-Friendly Family Retreat Near Chincoteague Bay!

Picture a peaceful family retreat near Chincoteague Bay at this vacation rental in Greenbackville! Situated in Captain's Cove, this 3-bedroom, 2-bathroom home comes complete with a fully equipped kitchen, a large furnished deck ideal for outdoor relaxation, and a den to provide extra space for your family. Head to the marina for an adventure on the bay, then enjoy an evening by the fire pit in the private yard. Whether seeking serenity or on-the-water fun, you'll love staying at this gem!

Charming Island Home "Sandy Pines"

Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is). The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

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 :)

"Beebe Lynn" - Houseboat Getaway

A "Tiny house on the water". Your home-base for exploring Delmarva! Beebe Lynn is a vintage 32 ft Carver, 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. Beebe Lynn 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!

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.

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.

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.

Tiny Gorgeous Waterfront Cottage

This cottage is 10 feet from the water. You'll wake up on a quiet slice of heaven. The road side faces the west for a beautiful sunset over the quiet corn field. The back side, faces the East. You look directly across at Assateague Island over the Bay. Our house is off the beaten path. This is great because it's an extremely quiet location, but also you are 11 minutes from anything. The closest store is 9 miles away. we love quiet coffees on the pier

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.