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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!🐴🦪🌅

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!

Nature's retreat @ the Bug-a-Boo. Beaches nearby

We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

Pearl in the Pines: bikes, kayaks, EV charger

Nestled in the shade of tall pine trees in the private community of Oyster Bay, "Pearl in the Pines" is a charming coastal retreat equipped to meet any need. This bright and beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly, making 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.

A Private Quiet Eastern Shore Estate

Relax with the whole family at this peaceful place to stay. The town of Atlantic is surrounded by must-sees. NASA, Chincoteague Island, Assateague Beach, NASA shuttle launches, the wild ponies, and Ocean City. All are within driving distance and are great attractions. Our home has 3 bedrooms, 2 baths, and lots of space in the house. Depending on the rainfall, there is a pond in the backyard. During the dry season (July - Sep) the pond could dry up. The pond is can be fished in when full.

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!

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

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!

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.

Rumbley Cottage on the Tangier Sound-Private Beach

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.

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.