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Experience coastal living at its finest in this meticulously preserved 1913 four-square home, perfectly positioned between Cape Charles'most coveted attractions. Just a leisurely one-and-a-half block stroll takes you either to the pristine beaches of the Chesapeake Bay or to the vibrant town park, where summer concerts, tennis matches, and recreational activities create a symphony of community life.

This distinguished residence, graced by Crepe myrtles that line its tranquil street, offers an elegant blend of historic charm and modern comfort. Four well-appointed bedrooms and one-and-a-half bathrooms provide ample space for both family living and gracious entertaining. The home's refined character shines through in its gleaming wood floors, while the upgraded kitchen boasts contemporary appliances for the discerning chef.

Outdoor living reaches new heights with both covered front and back porches, perfect for morning coffee or evening relaxation. The piece de résistance is an elevated screened gazebo nestled in the fenced backyard, accompanied by custom decking that creates an ideal setting for al fresco dining. Practical amenities include an outdoor shower for post-beach rinses and a dedicated fish cleaning station with sink – a nod to the coastal lifestyle.

Convenience meets charm with flexible parking options, including space for two vehicles via the rear alley access, complemented by ample street parking. Situated in the historic district, this home offers privileged access to Cape Charles' boutique shopping, dining, and cultural attractions, making it an ideal residence for those seeking a sophisticated coastal retreat.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- One adult dog is permitted with an additional pet fee of $200. Must be small to medium size (under 50 lbs.) and housebroken. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

We're pleased to offer you 'Utter East'! Tucked off of a quiet side street in the middle of the island, this home features everything you'd need for a wonderful, relaxing vacation. If you love outdoor space, you'll love the huge screened porch, expansive decks, and beautifully landscaped fire pit sitting area on the pond. Inside the home, downstairs you'll find the living room, an additional den/family room, eat-in kitchen, dining room, two bedrooms and a full bathroom. Upstairs features two more bedrooms and another full bathroom. Don't delay; this home will book quickly! "Where sky and water meet, Where the waves grow sweet, Doubt not, Reepicheep, To find all you seek, There is the UTTER EAST." - From "The Chronicles of Narnia" by C.S. Lewis

- Linens and towels are included with your reservation.

- No smoking/vaping is permitted on the premises, including porches and outdoor areas.

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Discover the charm of coastal living in this delightful 2-bedroom, 1-bath cottage nestled in a serene area north of Chincoteague town center. This home offers a unique blend of comfort and tranquil views of the surrounding marshland and creek. Watch the abundant wildlife from the comfort of your living room, adding a touch of nature’s television to your daily routine.

Inside, the home is accented with personal decor touches that provide a warm, inviting atmosphere. Though compact, the layout ensures efficient use of space, creating cozy yet comfortable living areas. Step outside and you're just a short drive from Assateague Beach, where wild ponies roam freely – a sight that never fails to amaze. For your everyday needs, Island Foods Great Valu is conveniently located nearby, and for a sweet treat, the Island Creamery can be reached within a few minutes' drive, offering the best ice cream on the shore.

This home is perfect for those looking for a peaceful retreat with the convenience of community features within reach. Make this cottage your own secluded getaway and enjoy the laid-back lifestyle that Chincoteague is famous for. Experience the joy of waking up to soothing water views and the melodious sounds of local wildlife every morning!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Newly available on the vacation home market, this two-bedroom, one-and-a-half-bath condominium offers a refined living experience in the heart of downtown Cape Charles. Seamlessly blending quality craftsmanship with simplistic, yet thoughtful, design - this home delivers an ideal mix of comfort and coastal charm.

Step inside to find a sun-splashed living room enhanced by skylights, an ambient fireplace, and a wall-mounted TV—perfect for relaxed evenings or rainy-day movies. The open layout flows effortlessly into the primary suite with king bed and the custom-tiled primary bathroom, revealing attention to detail at every turn. Upstairs, a second bedroom includes an adjoining powder room, offering privacy and convenience for discerning guests.

Where this home truly shines is outdoors. Ascend to the rooftop terrace, where panoramic views of the marina and Chesapeake Bay stretch before you. Entertain under the pergola-covered wet bar—ideal for sunset toasts or brunches with a coastal breeze. The terrace transforms the condo into an entertainer’s dream or a quiet retreat to recharge under the sky.

Situated mere steps from Cape Charles beachfront, you’ll be soaking in the salt air faster than you can say “flip-flop.” With boutique shops, the Cape Charles Distillery, local restaurants, and ice cream parlors within strolling distance, this bayside sanctuary keeps daily conveniences charmingly close. Even grocery runs are a breeze, with a Food Lion just minutes away.

Whether you’re hosting friends for rooftop cocktails or simply kicking back by the fireplace with a book, this home invites you to relax, recharge, and delight in the Cape Charles lifestyle.

PLEASE NOTE: 'Maryland' is one of 5 luxury apartments offered within the 'Cape Dunes' complex. This being the case, some amenities and spaces are shared. This includes the washer & dryer, ice maker and roof top terrace. Parking is on-street and not reserved. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Your home away from home... enjoy the water views, bring your boat and use your own dock, or just relax and listen to the whispering pines. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV, and PET FRIENDLY! Great views of Oyster Bay from the front and back decks, and there's a large screened porch for outdoor enjoyment. On the lower (first level) of the home you'll find a large open room with a Queen and 2 Twin beds, as well as a large utility room and bathroom with shower. The main living level (second level) of the home features the living room, kitchen & dining area, as well as 3 bedrooms (K/K/Q) and 2 full bathrooms. Note: This property has a 7 night minimum stay during all seasons.

-Parking only for 4-5 Cars

- SPECIAL NOTE: This rental home has a 7 night minimum year 'round. 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. Pet restriction: limited to two pets, cats are not permitted.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.