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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!🐴🦪🌅

Island House: Kayaks, Bikes, Beach Gear & Firepit

Welcome to Happy Ours! Relax with the whole family at this peaceful Chincoteague home. Walk to the park (Pony Swim!). This beachy cottage offers all the charm with plenty of space, in a quiet area with a huge property. This is a family home that we enjoy with friends & family year-round. We would love to share that experience with you! If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Chincoteague has to offer!

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!

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.

Rest A'Shored charming Chincoteague getaway

Spacious open floor plan great for entertaining family and friends with all the modern amenities you need! Eat inside at the large dining room table or enjoy the cool evening breeze outside on the fully screened in porch. 3 bedrooms and 2 full baths can comfortably accommodate 2 families with children or 3 couples. Located on Willow street, you are just a short walk to the Chincoteague carnival grounds and Main Street. We are dog friendly as we know they are really part of the family!

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 :)

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!

The Magnolia House ~Available Aug.24th 30th~

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.

Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

Location, Location, Location! Sunny Claire puts you in the heart of historic downtown Chincoteague, just minutes from Assateague Beach and the National Wildlife Refuge. Steps from top restaurants, shops, and attractions, this charming retreat features a 6-person hot tub, cozy porches with partial water views, and sunset-ready vibes. Enjoy a King Sleep Number bed, linens and towels provided, an outdoor shower, and a water filtration system for a carefree stay.

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!

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!

Summer's Seaside Cottage | Near Ponies & Beach

Welcome to Summer's Seaside Cottage -- a breezy, costal retreat designed for slow mornings, salty air, and unforgettable island evenings on Chincoteague Island. Whether you're here for the wild ponies, beach days, or simply to unwind, this is the kind of place that instantly feels like a vacation.