10 One of a Kind Places to Lay Your Head on Virginia’s Eastern Shore

Posh hotels, national brand lodging and five-star resorts can be found anywhere, but if you want to stroll miles of private beach, sleep with wild ponies in the yard or set up camp in a lodge on a private island the Eastern Shore of Virginia is the place for you. Get off the beaten path and find accommodations you’ll never forget.

A Private Off-the-Grid Island
Holly Bluff Guest House
Holly Bluff Island, VA
Everyone has dreamed of escaping to a private island with just the bare necessities and their swim suit at one time or another. On Virginia’s Eastern Shore you can make that dream a reality. Holly Bluff is a privately owned island off the tip of the 70-mile peninsula that makes up the Eastern Shore. Getting there is half the fun.

Holly Bluff Guest House

The island is accessible by kayak with the help of an outfitter or by boat. A sandy beach gives way to a network of boardwalks that connect to the guest house, which was originally built as a hunting and fishing lodge in the 1930’s. Marshes and water views surround the house. Inside, the guest house has no electricity. Propane is used to power lanterns, heat water and run refrigerators and a stove. The water at the house comes from a cistern. It is a truly off the grid getaway. When it comes time for dinner, you can cull oysters and pull crab pots from along the shoreline for the freshest seafood feast possible. After the sun sinks over the water it’s time to enjoy the peace and quiet, no traffic noise, no street lights, just the sound of the water lapping against the shore.
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A Yurt by the Bay
Kiptopeke State Park Yurt
Cape Charles, VA
Camping has a certain romantic appeal, but sleeping in a tent on the ground is not for everyone. A yurt offers the best of both worlds. You’re out in nature, cooking over a fire, without modern convenience, but you get to sleep in a real bed, it is heated and air conditioned and there is enough space inside for lounging. What makes the yurt at Kiptopeke State Park extra special is that it has a spectacular view of the Chesapeake Bay.

Kiptopeke State Park Yurt
Kiptopeke State Park Yurt

The yurt is also surrounded by a large wooden deck where you can cook, eat meals or watch the sunset over the water. The yurt also has electricity and a water spigot. There’s even a fridge to store your food in. The bathhouse where campers can clean up is just steps away. There is plenty to keep you busy inside the park including a beach, a fishing pier, kayak and bike rentals, nature trails and a boat launch. The concrete ships that serve as a breakwater off the park’s coastline are an attraction in themselves.
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A Safari Tent Under the Stars
Chesapeake Bay KOA
Cape Charles, VA
Camping on the Beach is great, but before you can relax and enjoy nature someone has to pitch the tent and set up the sleeping bags, right? Not if you stay in a safari tent at Chesapeake Bay KOA. These luxury tents have front porches, comfy queen beds and a sitting area. Plus, they have a great view of the Chesapeake Bay and are just a few steps from the resort’s private beach.

Camp in luxury in a safari tent at Chesapeake Bay KOA. Chesapeake Bay KOA Photo

A Modern Retreat with Acres of Private Beach
Pickett’s Harbor Beach House

Cape Charles, VA
Nothing can make you feel more like a celebrity than stealing away to a sleek, modern getaway tucked down a wooded lane with 27 acres of private beach. The house may be all clean lines on the outside, but that doesn’t mean it’s cold on the inside. The modern interior is accented with comfy, beachy furniture in the great room, fluffy comforters on the beds and touches of coastal decor.

Goffigon Home JPEGS_Page_12
Picketts Harbor Beach House. Photo courtesy of Tom Goffigon.

The sleek kitchen is sure to make you feel like a chef. If you’re more of a grill master you’ll love the setup on the porch. Outside, a deck wraps around the house with views of the water. A boardwalk connects the house to the beachfront, which stretches for miles in either direction and it’s all yours.
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A Victorian Cottage on a Tiny Island
Pretty Byrd Cottage
Pungoteague, VA
In case an 18th Century estate way off the beaten path isn’t secluded enough for you, Evergreen Farm is home to an even more private abode. Pretty Byrd Cottage is a dollhouse-like Victorian cottage perched on a tiny island in the middle of a lake on the estate. Guests can reach the cottage by taking a short walk across a footbridge or they can opt for the scenic route and navigate a paddle boat around the lake. There are plenty of places to enjoy the view outside with two balconies and a deck. The cottage is surrounded by little gardens that make it even more picturesque. Inside the house is furnished with Victorian decor, complete with a dining room with a great view. It’s the perfect place for a romantic getaway for two, but the extra space in the sleeping loft means it could also be a quiet family getaway.
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A Historic Waterfront Home
If you’re a history buff you’ll love this house. The oldest part of this home on the Eastern Shore of Virginia’s Atlantic coast dates back to the 1600s and played a role in the Revolutionary War. The house even has a ghost story in the history books. The house is situated on 50 acres and has waterfront views, including a glimpse of the barrier islands that separate the Eastern Shore from the Atlantic. A network of wetlands separates the property from the water, which makes for great kayaking and nature watching. Some of the rooms are decorated to give a nod to the home’s deep roots, while others have been given a pop of color. The large dining room and the plethora of bedrooms make this house a great destination for the whole family.
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A Sprawling Waterfront Estate
Matchotank Country Home

Onancock, VA
If you read Jane Austen novels and swoon over the idea of having a rambling manor house with a park-like setting and a pond to stroll around, look no further than Matchotank Country House. The 3,800 square-foot historic farm house is situated on 50 acres with waterfront views, a stocked freshwater pond and a private dock. This getaway is perfect for kayakers and boaters as well, with easy access to Matchotank Creek and the Chesapeake Bay.

Matchotank Country Home.

The house was designed for relaxing, with an enclosed porch and a massive slate patio overlooking the water. Inside, living spaces like the reading room and den have a cozy feel thanks to fireplaces and water views. There are plenty of fun activities without ever leaving the grounds. There is a paddle boat, a row boat, a horseshoe pit, crabbing off the dock, fishing in the pond and plenty of wildlife watching. Bikes and kayaks are also provided.
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A Tiny Cottage on Main Street
Chincoteague, VA
If you dream of owning a tiny house someday there is a place for you on Chincoteague. This studio-style cottage is in the heart of downtown Chincoteague with easy access to restaurants, shops and entertainment. It might be pint-sized, but this little house has everything you need for an island getaway. The main room has a kitchen equipped with a fridge, microwave and hotplate. There is a small dining area and a living room with a sleeper sofa. The sleeping area houses a bed big enough for two. Off the main room is a bathroom with a shower. This coastal cottage is as cozy as can be and is located close to all the fun of downtown Chincoteague.
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The Room Where Misty of Chincoteague Was Made Famous
Miss Molly’s Bed and Breakfast
Chincoteague, VA
The most famous Chincoteague resident of all time was a pony named Misty. She became a star thanks to Margurite Henry, who wrote the book Misty of Chincoteague about the wild Chincoteague pony and two children who dreamed of buying her at the annual auction where the Chincoteague Volunteer Fire Company sells foals from the wild pony herd.

Miss Molly’s Inn

The book was published in 1947 and Henry penned it in a room at Miss Molly’s. You can still stay in that room today. The Margurite Henry room has a luxurious king sized bed, a sitting area and a private bath. There’s even a fireplace. The inn itself also has plenty of amenities, from bikes to beach chairs and snacks. They’ll even pack a lunch for you to take to the beach.
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A Cape Cod Cottage with Ponies in the Yard
Baywatch Cottage

Chincoteague, VA
If you’ve always dreamed of seeing the Chincoteague ponies then this house is a must. You can sip coffee on the deck while watching ponies in the yard. This house is surrounded by nature’s beauty. It faces Oyster Bay to the south, salt marsh to the north and a pony pasture to the west is filled with some of Chincoteague’s famous ponies. There is a deck and a dock outside so guests can take in the scenery or watch the abundant wildlife. Inside it has plenty of room for the whole family, as the house sleeps six.
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For a complete list of accommodations on Virginia’s Eastern Shore click here.

You may also like: Six Great Beaches on Virginia’s Eastern Shore

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Annual Fests for Foodies, Virginia’s Eastern Shore

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