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La Vie

3 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Pool
Internet

Views! Views! Views!  Enjoy the expansive panorama from all three levels of this prime waterfront location on Chincoteague Bay. With 180 degrees of natural beauty graced by blissful sunsets, “La Vie” invites you to live the life at its most relaxed.

As soon as you enter the home, its light and airy floor plan lifts your spirit, calms your mind, and promises to rejuvenate your body. Meticulously maintained, continuously updated, La Vie features a fully equipped granite counter gourmet kitchen with a new large six burner induction stovetop.  You’ll likely want to cook, or eat, or relax as it gives  you a chance to take in the breathtaking water views.  Watch the sun set from anywhere in this large open space second floor central living area.

The home’s entry level features a newly furnished queen bedroom with sliding glass doors opening to the incredible views on your waterfront deck. Plus another large bedroom has two twin beds!  If you need another bed yet, pull the curtain shut to a cozy alcove and sleep soundly on the full sized sofa bed. Extra privacy abounds in the 3rd floor suite!  Enjoy more of the spectacular water views from your king-size bed, private balcony, or wicker lounge chairs.  Immerse yourself in the large jacuzzi-style tub. La Vie offers plenty of space to share this retreat for friends and family!

Stream away on any one of the four new UHD 4k smart TVs with multiple HDMI ports.

The amenities aren’t confined to the house:

  La Vie also includes access to a 700-foot-long shared pier for fishing or launching kayaks.

  Don’t forget your boat! La Vie includes exclusive use of boat slip #1

  A summertime pool located right across the street.

  Shaded parking directly under the unit.

  The historic fireman’s carnival grounds across the street; open most July weekends.

  On Pony Swim week,  the world famous Chincoteague Ponies parade right in front of La Vie (July).

  The town July Fourth fireworks are launched about 100 yards away. 

However long your stay may be, you’ll make lasting memories and take the positive energy, beauty, and majesty of La Vie and its surroundings home with you. La Vie, “the life,” is short of La Vie en Rose, which can mean life is as beautiful as you wish to see it.

- 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. All pets must be disclosed prior to arrival. Pet restriction: No cats.

- 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

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Herbie's Hideaway

3 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beautiful views of Assateague Island. The oversized chef's kitchen offers ample room for family gatherings and preparing meals, and it compliments the spacious dining area that opens up to the large screened porch. Beautiful custom windows and large sliding doors complete the open and airy floor plan. The geothermal heating/ac system lends to your ultimate vacationing comfort! Close to Memorial Park (playground, basketball, tennis, trails, water access) and directly across the street from a family restaurant! For larger groups or family reunions, check out nearby Moon Rising or Wildflower!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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.

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Almost Heaven

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Internet

Private pier with boat docking, Waterfront, Pet friendly, Internet, A/C, Fireplace, Charcoal grill. Vintage charm with all modern comforts!

Welcome to your new favorite island getaway! This charming Victorian cottage on Chincoteague's popular South Main Street offers the perfect blend of traditional character and modern comfort. With 3 bedrooms and 2 bathrooms, there's plenty of space for family and friends to unwind after a day of island exploring and adventures.

Step onto the open front porch and prepare to be amazed — breathtaking bayside sunsets await you nearly every evening. Pour yourself something refreshing, kick back in a rocking chair, and watch as the sky transforms into a canvas of orange and pink hues over Chincoteague Bay.

One of this home's standout features is the private pier extending directly into the bay, complete with boat dockage capabilities. Imagine morning fishing sessions, dropping a crab line to try your hand at catching dinner, or evening cruises right from your rental home! No need to haul your boat to a public launch — your nautical adventures begin here.

Traveling with 4-legged family members? No problem here - 'Almost Heaven' welcomes your pet(s)!

Location? Simply perfect. You're just minutes from downtown's delightful shops, restaurants, and even the downtown movie theater. Grocery runs are a breeze with Island Foods just a short drive away. For summer fun, Maui Jack's Waterpark is nearby, and the stunning Assateague Beach is waiting to capture vacation memories, and for your footprints in the sand.

The primary bedroom on the first floor offers a peaceful retreat after long days exploring island trails or collecting seashells. The second floor features two more bedrooms and a full bathroom (shower only). This isn't just a rental — it's your ticket to the relaxed island lifestyle you've been dreaming about. Make it your "home away from home'... at the beach!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- 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.

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Artist Apartment

2 Bedrooms
1 Bath
6 Guests
Wachapreague
Water View
Gas Grill
Screened Porch
Internet

Discover coastal charm and artistic flair at this newly renovated condo nestled in the picturesque village of Wachapreague, Virginia. Perfect for those who love the outdoors, this "Artist Apartment" sits above the Current Reflections-Fine Arts Gallery, providing a unique living experience that merges creativity with comfort. Guests have their private entrance at the back of the Art Gallery building, ensuring your peace and privacy on the second floor, including the rooftop deck access.

Spanning the second floor, this condo boasts two versatile bedrooms and a well-appointed kitchen ready to handle your culinary adventures. Whether you're a novice cook or a seasoned chef, you'll find everything you need to whip up delicious meals. The living spaces are furnished for comfort and style, ensuring a cozy ambiance that feels like home.

Step outside to the exclusive low roof deck, where dining, sunning, and relaxing take a whole new meaning. Complete with partial cover, an outdoor TV, and a fridge, this space is tailor-made for enjoying those beautiful coastal sunsets.

When you're ready to explore, the location could not be better. The condo is just footsteps away from delicious dining options like the Island House Restaurant, famous for its "Frozen Orange Crushes" and fried flounder. Nature lovers will appreciate the proximity to eco-tours, kayak rentals, and water taxis to nearby barrier islands – perfect for bird watching and shelling excursions.

Immerse yourself in the serene and artistic lifestyle of Wachapreague in this one-of-a-kind rental. Whether you're here to fish, kayak, or simply unwind among the creations of local artists, this condo offers the perfect retreat for every endeavor.

- No smoking is permitted on the premises. 

- Linens and towels are provided for your stay. 

- 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.

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Pocahontas

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Nestled in the vibrant heart of Cape Charles, this exquisite one-bedroom condominium represents bayside town living at its most refined. Recently transformed through meticulous renovation, the home seamlessly blends simplistic sophistication with coastal charm to create an atmosphere of understated luxury.

The thoughtfully designed interior showcases an open living space with a fireplace and large TV, sumptuous primary bedroom featuring a king-size bed that promises restful nights after sun-soaked days. Step through the doors onto your private balcony, where panoramic views of downtown and the marina create an ever-changing tableau of maritime activity and small-town vibrancy.

Culinary enthusiasts will appreciate the full kitchen appointed with premium new appliances, inviting both casual meals and ambitious dinner preparations. The custom-tiled bathroom elevates daily routines to spa-like experiences, reflecting the property's commitment to refined comfort.

Location defines true luxury, and this residence delivers magnificently. Mere blocks from the shimmering shores of the Chesapeake Bay, you'll find yourself effortlessly immersed in the coastal lifestyle. The convenience of having Cape Charles' most coveted attractions just steps from your door cannot be overstated—savor artisanal spirits at the local distillery, browse distinctive boutiques and art galleries, indulge in gourmet ice cream, or select from diverse dining options.

For the discerning individual seeking a harmonious blend of tranquility and accessibility, this sanctuary offers a rare opportunity to embrace the quintessential Cape Charles experience.

PLEASE NOTE: 'Pocahontas' 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.

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Anchors Away

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Pet Friendly
Gas Grill
Pool
Internet
Outdoor Shower

Welcome to "Anchors Away," a captivating waterfront home now available for rent, offering an unparalleled living experience. This remarkable property boasts four generously sized bedrooms and three well-appointed bathrooms, providing ample space for comfort and privacy.

Nestled in a vibrant community known for its welcoming atmosphere and scenic beauty, this home is designed to impress with its stunning waterfront views that can be enjoyed from the spacious decks - perfect for entertaining or simply unwinding in nature's embrace.

The first-floor suite offers convenience and accessibility, ensuring that everyone can enjoy this home's charm without compromise. The interior is just as impressive, featuring granite countertops and stainless appliances that add a touch of elegance to the functional and stylish kitchen. 

With parking space for up to four vehicles, you'll find this property not only beautiful but also practical. The pet-friendly policy ensures that your beloved companions can join you in calling "Anchor's Away" home.

This house is more than just a place to vacation; it's an opportunity to make life-long memories for those who value beauty, community, and comfort. Whether you're gazing at the serene waters from your deck or enjoying the modern amenities inside, this home invites you to live your best life.

Don't miss the opportunity to make "Anchor's Away" your new haven. Contact us today to experience firsthand everything this exceptional rental property has to offer.

- 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: No cats

- 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.

- Community amenities require passes for an additional fee.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities. No Sunday check-ins or check-outs are permitted. 

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Dragonfly Point

4 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

"DRAGONFLY POINT" is a magnificent waterfront property on Oyster Bay & canal. Surrounded by water on three sides of the home, you see the bay and canals from every window! The abundance of decking for entertaining will amaze you with easy access on both floors. Upper family room/loft with unobstructed views. The home has beachy-chic feel with built in bookcases, shiplap, custom fixtures and bathrooms, and more. Two master bedroom suites - upper and lower. Totally fenced in yard that has mature plantings, kayak launch with concrete pad, 120' pier that extends into the bay, comfortable screened porch and much more! Many updates recently including washer & dryer, brand new kitchen & appliances, new bathrooms, etc. SIMPLY BREATH TAKING VIEWS! Come for a stay at Dragonfly Point - it's one you surely will not forget!

- This property has a 7 night minimum stay year 'round. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- 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.

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Touch of Grey

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Internet
Outdoor Shower

Welcome to "Touch of Grey," a delightful waterfront rental that blends comfort, style, and convenience into a perfect living space suitable for a variety of lifestyles. This well-appointed house includes three bedrooms, two bathrooms, and a range of updated amenities that ensure a seamless living experience.

Inside, discover a thoughtful layout featuring smart TVs throughout, high-speed WIFI, and a mix of privacy and social spaces that cater to both relaxation and entertainment. The screened porch offers a serene retreat, perfect for enjoying the outdoor air without the bother of pests, and the open deck invites you to bask in the stunning views that surround you.

Step outside to explore the  outdoor space that this property generously offers. A large deck overlooks the tranquil waters, ideal for peaceful mornings or lively evening gatherings. The highlights of the outdoor area include a personal boat dock, which provides immediate water access for boating enthusiasts. Meanwhile, the fire pit setup paves the way for memorable weekend cookouts with friends and family. This home also provides 6 bikes for guest use! 

Pet-friendly provisions mean that your beloved animals are just as welcome as you are, making it a true home for everyone. Functional features are balanced with aesthetic touches to create an inviting environment throughout.

"Touch of Grey" not only promises a picturesque setting but also ensures practicality with its various updates and amenities. Whether you’re drawn to the waterside way of life or simply seeking a tranquil place to call home, this property addresses all facets of modern living. Experience the blend of natural beauty and contemporary comforts in a place ready to be called home.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- 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.

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Hailey's Round House

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Screened Porch
Internet

Check out Chincoteague’s newest Piney Island vacation rental! Hailey’s Round House is in a prime location on Chincoteague, in a quiet development road but just a short walk to the bridge to Assateague and the Maddox Boulevard shops and restaurants!  You could take a bicycle or short drive to the Assateague beach and access to all of the bicycle trails around Chincoteague and Assateague to enjoy the wild ponies or many of the restaurants on Chincoteague.   

Hailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed.  You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay! 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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.

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Seas the Day at Bay Creek

2 Bedrooms
2 Baths
6 Guests
Cape Charles
Town & Country
Pet Friendly
Gas Grill
Pool
Internet

Welcome to 'Seas the Day at Bay Creek' - a beautiful townhome located at Churchill Downs in the coveted Bay Creek Resort in Cape Charles, VA. Offering a perfect blend of comfort and luxury, you'll be "wowed" from the moment you walk through the door of this discerningly and thoughtfully decorated home. With two designated  bedrooms and two full bathrooms, and a bonus private sleeping area, this spacious home provides an ideal living space for individuals and families alike.

Step inside and be greeted by the elegant features of this home. The granite countertops in the professional chef's kitchen are not only visually stunning but also functional for all your culinary adventures. Enjoy your morning coffee in the cozy breakfast nook, or indulge in a meal. The modern and open concept of the kitchen is perfect for entertaining, and if you appreciate wine, you'll love the convenience of having a dedicated wine fridge to store your collection. The high ceilings, TV and fireplace add character and warmth to the living area. If you need more space or privacy, the sunroom offers windows with abundant natural light from every angle, and a large 65" TV awaits all of your entertainment needs. 

The primary bedroom is conveniently located on the first floor and offers its own private bathroom, ensuring relaxation and tranquility after a long day. The second bedroom (loft-style) encompasses the entire second level and features a Queen size bed. The 3rd sleeping space is completely private and leads to the outdoor patio space. This room offers a cozy sleeper sofa. 

Outside, you'll find a beautifully landscaped patio complete with comfortable furniture and a grill - perfect for hosting gatherings or simply enjoying some outdoor relaxation. This set up is sure to host one of your most memorable cook-outs! Your fur babies will also enjoy the large fenced in yard!

This rental home also includes access to community amenities such as a pool, gym, private restaurant, and even an optional golf course. Nature enthusiasts will appreciate the nearby nature preserve, offering opportunities for peaceful walks or jogs in nature's embrace. Don't miss out on the chance to make this gorgeous duplex home your new "home away from home"!

BED CONFIGURATION: Primary Bedroom 1 = King bed; Bedroom 2 (Loft) = Queen bed; Private Sunroom = Queen sleep sofa; Living Room = Queen sleep sofa

SPECIAL NOTES:

This rental home is NO SMOKING and PET FRIENDLY (with fee). Pet fee is $200 per pet. All pets must be disclosed prior to arrival. 

Linens and towels are included with your reservation.

Usage of the Bay Creek Resort amenities requires an additional fee of $75 per day*.

BAY CREEK RESORT AMENITIES:

Waterfront area perfect for kayaks, canoe, fishing or crabbing.

27 hole World-class golf course (requires additional golf fee).

Golf lessons and clinics available for all skill levels.

Member lounge will billiards and entertainment.

Cardio and weight training studio.

Two outdoor pools w/ decks and furniture.

350 acre Nature Preserve w/ trails and wildlife viewing.

Clubhouse with private restaurant and dining experiences.

Structured activities and programs such as bird watching, paddle-boarding, beach yoga, kid's camps & more. 

*Fee is subject to change without prior notice or authorization. Bay Creek Amenity offerings can be seasonal and may change without prior notice or authorization.

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Seas the Day

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Screened Porch
Pool
Internet

You will LOVE the quiet duplex community where this home is situated. Bright, open floor plan, with adjoining screened and open-air porches - perfect for sipping coffee in the morning or relaxing with a cool drink after a day at the beach. The first floor bedroom offers a private bathroom and the sweetest window nook - bring your book! Two additional bedrooms upstairs share a full bathroom and all bedrooms are tastefully decorated in their own fun personal themes! Hosting a group that requires more space? Rent Seas The Day's sister, 'Sea La Vie', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bunk bed + a Twin Trundle bed!**

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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.

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Stingray

2 Bedrooms
2 Baths
4 Guests
Chincoteague Island
Waterfront
Internet

Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, features all amenities, as well as master bedroom suite with king bed & waterside balcony. Many extras like a flat screen TV and a Lazy Boy leather recliner. The open floor plan is great and features a breakfast bar between the kitchen & dining area!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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.

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