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Historic Charm & Modern Comfort : Downtown Escape

Surrounded by an array of restaurants, bakeries and a variety of unique boutiques and experiences, this apartment offers the perfect blend of charm and convenience. Juliette balconies invite fresh air and natural light, creating a Parisian-inspired ambiance. Inside, a fireplace creates a cozy setting. The state-of-the-art kitchen, designed in a striking 1950s vintage style, features Smeg appliances and bold crimson red accents, seamlessly blending retro elegance with modern functionality.

Bay Breeze on Tazewell (Sun-Sun rental June-Aug.)

Bay Breeze on Tazewell is a recently remodeled Cassatt cottage with historic charm and modern amenities. The home includes a fabulous, sunny kitchen stocked to meet your needs. We provide fresh linens and towels for your stay. In the shed, you will find lots of items for the beach, a wagon, and bikes which we are happy to share. Bay Breeze is just a short walk to the beach, various restaurants, boutiques, and marina. If our home is not available, try our new Airbnb home ...Harbor View!

Coastal Red Barn Retreat

Located on the coastal seaside of Cape Charles, this barn was originally built in 1893. It has been lovingly restored to reflect the area's rich history, while providing modern comforts for today's guests. The Red Barn is nestled in the midst of scenic farmland, yet is only a few miles from the charming downtown, with its eclectic restaurants and unique shops. Enjoy the fresh breezes of the Atlantic and watch the sunrise over the fields from the comfort of the barn's private deck.

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

"Live Life Sunnyside Up" - Minutes From The Beach!

Welcome to "Live Life Sunnyside Up" on the Shore! Take a trip off the busy beaten path and kick your feet up at our little slice of paradise. Kid friendly with plenty of amenties for you and your family. On a quiet street, less than 4 miles from the historic town of cape charles and beach, get ready to take a load off and enjoy the many treasures Cape Charles has to offer! Just 5 short minutes from the Oyster Boat Ramp, fishermen are sure to find their honey hole here!

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Historic 3BR • Spacious • Fire Pit + Wood

• 3BR/2.5BA, 4 blocks to beach & downtown • Very spacious, open-concept w/ 2 living areas + kitchen peninsula seating 6—plenty of room to spread out • Private backyard w/ fire pit + Adirondack chairs (wood for 1st fire included!) • Spacious deck over fenced yard + front porch for morning coffee • Master bath w/ walk-in shower, dual sinks & closet • Outdoor shower + cornhole • Paddle boards, beach toys & towels • Dog-friendly (well-mannered pups welcome

The Ladybug - arcade, dog-friendly, firepit, & EV

A peaceful, design-forward farmhouse escape just minutes from Cape Charles. Packed with unique features like a retro arcade, Peloton, firepit, Ninja SLUSHi, EV charger, Roku TVs with private listening, smart speakers in every room, and Spotify speaker groups. Guests love the vinyl collection, fast WiFi, chef-ready kitchen, and views of the Magothy Bay Preserve. Pet-friendly, kid-friendly, and built for connection and comfort.

Eastern Shore Secluded Getaway

Have fun with the whole family at this cabin inspired fully furnished apartment. Located 20 minutes from Cape Charles our dwelling sits on 175 acres of property. The Sunset views are one of a kind and the location is very remote. There is one bedroom, a bunkbed, and also pullout couch for sleeping spaces.  The kitchen has all the amenities of home and there’s also a full dining room area.  We do provide linens and towels.