Holiday houses in Greenbackville

4.92 out of 5 average rating, 87 reviews

A gravel driveway leads towards a rustic boathouse with weathered wooden siding, framed by tall grasses and marshland. The iconic Chincoteague lighthouse can be seen in the distance, completing the scenic view under a clear sky.

Cabin in Chincoteague

The Boathouse: Charming & Historic Waterfront Stay

Welcome to the Boathouse! You read that right: Boathouse (not House Boat!) This house, which has been part of our family for generations, is the perfect home-base while you visit the special island of Chincoteague! Watch the lighthouse from across the marsh, go for a canoe ride through the channel, catch some crabs off the private pier, or make your way to the famous Assateague Beach - this cozy, quirky house is perfect for those seeking a unique and memorable adventure on Chincoteague Island!

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4.96 out of 5 average rating, 70 reviews

The exterior of a charming white cottage is showcased, featuring two sets of stairs leading to the front porch. The well-maintained lawn is punctuated by a small garden area, and a decorative figure can be seen near the entrance.

Cottage in Chincoteague

Waterfowl Watch Chincoteague & bikes Fall dates

Small family-friendly two bedroom cottage in a quiet area with a slight view of Little Oyster Bay. 1 mile to Maddox Blvd/ 3 miles to Assateague Is. A queen,bunk beds w/trundle & sleeper sofa. Private back yard, property is cute & clean, it is a beach cottage not a luxury resort. Get back to nature or explore many shops and activities. Fire pit,outdoor seating,charcoal grill, backyard games, Bikes(waiver required). Rental kayak service available year round. Jan-March monthly is avail inquire

LocationFamilyWalkability

A modern two-story home with a striking blue exterior stands amidst a backdrop of trees. A wide front porch features white railings and steps leading to the entrance. A spacious driveway provides ample parking space, with natural landscaping visible on the property.

4.97 out of 5 average rating, 77 reviews

BarDown | Chincoteague Retreat near Ponies & Beach

BarDown on Chincoteague Island is a brand new custom home built entirely to serve as the PERFECT beach house! Think relaxing stylish & functional. Envision quiet mornings with coffee on the front porch & enjoy afternoon cocktails on the screened in porch or a cookout on the back deck. All while overlooking quiet undisturbed wetlands and the neighboring pond. Walk to Veterans Memorial park & Explore all that the island has to offer BOOK WITH US NOW to experience your next amazing beach vacation!!

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A hot tub is situated on a wooden deck, bubbles rising gently from the water's surface. The vibrant blue exterior of the house is contrasted by pink trim. Sunlight reflects off the hot tub, creating a bright and inviting ambiance. A screened porch and balcony are visible in the background.

4.98 out of 5 average rating, 57 reviews

Hot Tub. Fire pit. Fenced Yard. Games. Downtown.

Mermaid & Mare – A Downtown Retreat with Hot Tub, Firepit & Pet-Friendly! Escape to an island retreat with two spacious bedrooms, each with an en-suite bath. First-floor bedroom – King bed, walk-in shower, deck access with hot tub. Upstairs bedroom – Jacuzzi tub, balcony with bay views. With 4 beds (1 King, 3 Queens), there’s room for family & friends. Amenities: Hot tub, firepit, cornhole & pet-friendly backyard, Smart TVs, screened porch, & bay-view decks. Walk to restaurants, bars & shops.

LocationFamilySleep quality

A spacious living area features a large sectional couch and a coffee table, surrounded by wooden flooring. A world map adorns the wall, and natural light streams in through the windows. The open layout flows into a dining area visible in the background.

5.0 out of 5 average rating, 58 reviews

The Magnolia House ~Linens Included~

You and your family will love this 100 year old fully restored home with its original hard wood floors, brand new chef’s kitchen, the 75’ TV and the extra large couch. Plan to pack your beach towels, your favorite swim suit and make yourself at home here in our Magnolia House. Located only 2 blocks from Maddox and only 5 miles from the beach. The bike trail to the beach starts right in our backyard. We hope to have created a space you can’t wait to come back to.

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Guest suite in Chincoteague

A cozy bedroom features a white, wooden bed frame with a floral-patterned coverlet. Two pillows and a decorative cushion rest against the headboard. A bedside table holds a lamp, and natural light enters through a window with soft curtains.

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!

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4.94 out of 5 average rating, 361 reviews

4.94 out of 5 average rating, 130 reviews

A modern kitchen is presented with white cabinetry and stainless-steel appliances, featuring a refrigerator, microwave, and coffee maker. A dining table is set for four, and a cozy seating area with a blue couch is visible. Natural light enters through a window, enhancing the space.

Cottage in Chincoteague

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!

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5.0 out of 5 average rating, 17 reviews

Captain's Loft

Relax with the whole family at the Captians Loft! A peaceful place to stay. Step into a sun drenched sanctuary designed for fun and relaxation. Discover the best of Chincoteague right from your doorstep! Captains Loft is perfectly positioned for foodies and explorers alike. You are just a short, breezy walk or bike ride from three of the island's most legendary spots: Captain Zacks restaurant, Island Creamery and Steamers!

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4.99 out of 5 average rating, 266 reviews

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

September 12-16 available. 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. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

ValueFamilyBathroom

5.0 out of 5 average rating, 14 reviews

Sialang - Waterfront, Pier, Hot Tub & Kayaks

Located just a few miles from Assateague Beach & the Chincoteague National Wildlife Refuge. Relax & enjoy picture perfect sunsets from this beautiful waterfront home. Private pier on Chincoteague Bay is the best spot for birdwatching, crabbing & kayaking (3 provided). Spend evenings on the screened in porch, relaxing in hot tub or enjoying the waterfront views from one of two spacious living rooms.

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Guesthouse in Pocomoke City

A comfortable living area features a spacious sectional sofa with decorative pillows, paired with two accent chairs. Light-colored walls and carpeting create a neutral backdrop, while a television rests on a wooden stand opposite the seating. Natural light is offered through nearby windows.

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.

LocationFamilyParks

4.94 out of 5 average rating, 193 reviews