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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.

Hosta Cottage

1 Bedroom
1 Bath
2 Guests
Mainland
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

There is a fanciful quality to this secluded property where nature’s beauty and luxurious accommodations coexist in quiet harmony.    Located on the banks of Holden’s Creek, a headwater of the Chesapeake Bay and a 20-minute drive to the pristine white sand Atlantic beach on Assateague Island, The Creek Guest Cottages are private, convenient, and offer bespoke modern amenities. Explore life off the beaten path and take a true vacation. Whether you are kayaking or paddle boarding on the creek, sitting by the fire pit, biking down country roads or going to the beach, you will find plenty to do or enjoy doing nothing at all.  The views of the creek are magical at any time of the day or night from inside your cottage or from any vantage point on the 3-acre property. The cottage has been designed and decorated by a professional interior designer.

'Hosta Cottage' has partnered with our friends at Sun Outdoors Resort (located less than 2 miles from the house) so that all guests may enjoy the fun resort amenities FREE OF CHARGE. This extra bonus includes a private beach w/ water rentals, pool, playground, "snak shak", comfort stations & more! 

On-site amenities include:  a gas grill, 20’ radius fire pit, 2 kayaks, a SUP, and 2 bicycles.  There is a boat launch on the property and two docks (one floating). Linens and towels are provided.

The Hosta Cottage: 850 square ft. Full Kitchen and Laundry. French Limestone Floors and tiled bathroom. Sleeps 2 (Queen Bed). Separate Private Outdoor Dining area (not included in square footage above). Outdoor Shower. Smart TV. WIFI.

In addition to Hosta Cottage, the compound is also home to two other luxurious dwellings: Porter’s Barn and Creek House. All combined, The Creek Compound will accommodate 18 with no parking problems. Please note that this listing is for Hosta Cottage only; the other two homes - Creek House and Porter's Barn - must be booked separately. A direct inquiry should be sent for special event pricing or if you wish to rent the entire compound.

- 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 one small dog only.

- 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.

Star of the Sea

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Pet Friendly
Gas Grill
Internet

Introducing a charming, newly renovated house, offering a perfect blend of comfort and convenience. This single-family home features an inviting sunroom, a brand-new kitchen, four well-appointed bedrooms, including a serene primary bedroom, and two modern bathrooms, all professionally decorated with a delightful beach theme.

Designed to accommodate up to eight guests, the house boasts spacious rooms that ensure ample space for relaxation and entertainment. The living areas flow beautifully outdoors to a superb deck, ideal for enjoying your morning coffee or sunset dinners, surrounded by a spacious yard.

Nestled in a vibrant neighborhood, the property promises a vacation of ease and accessibility. It’s centrally located near the heart of the town, close to a pristine beach, restaurants, and family-friendly activities, including mini-golf and Maui Jack's Waterpark. Nature enthusiasts will appreciate the proximity to the Assateague Island National Seashore, a spectacular location for wildlife and scenic views, while the nearby Downtown Chincoteague Waterfront Park provides excellent opportunities for leisurely activities.

Experience the joy of living where every day feels like a vacation. This retreat is not just a place to stay, but a home away from home. Come and see for yourself!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Home is pet friendly with additional pet fee. 

- 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.

Surf & Turf

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Charcoal Grill
Gas Grill
Internet
Outdoor Shower

Welcome to your new coastal retreat on charming Chincoteague Island! This delightful three-bedroom, two-bathroom home offers the perfect blend of comfort and convenience for those seeking a relaxed seaside lifestyle.

Step inside to discover a thoughtfully updated interior that's clean, bright, and vacation ready! The home features not one, but two living room areas—because sometimes you need some extra space and a separate sanctuary for escaping when someone insists on watching that show you can't stand. Whether you're entertaining guests or simply enjoying a quiet evening, you'll appreciate the flexibility this layout provides.

Located just off South Main Street, you'll enjoy easy access to everything this beloved island community has to offer. Nature and fitness enthusiasts will appreciate the proximity to Veteran's Memorial Park - perfect for morning walks, afternoon picnics or letting the kiddos expel some energy! Adventure seekers can head to Maui Jack's Waterpark for family fun, while the stunning Assateague Beach beckons with its pristine shoreline and legendary wild horses roaming freely along the sand.

This modest, yet inviting, home captures the essence of coastal Virginia living without unnecessary pretense. It's comfortable, practical, and positioned in one of the most enchanting island communities on the Eastern Shore!

- 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.

Heron's Cove On Salt Meadow

4 Bedrooms
5 Baths
12 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Peaceful and stunning waterfront home! Located on a quiet side-street, Heron's Cove features a reverse floor plan with all bedrooms on the first floor, and the main living-level on the second floor. This allows you to capture and maximize the fabulous bay views! The second floor also features a great room with cathedral ceilings, fully equipped kitchen, gas fireplace and screened gazebo. In addition, there's multiple open decks and a shared dock (with Egret's Cove) into Little Oyster Bay. There are three bedrooms that each have a king size bed, and one bedroom that has two sets of bunk beds. Each bedroom has a private bath. Luxurious comfort while surrounded by Chincoteague's natural beauty and wildlife! Floor Plan: Downstairs (first level) features 4 bedrooms, all with attached private bathrooms. Two of the downstairs bedrooms and the sitting area have private waterside balconies. Upstairs features an open floor plan with the kitchen, living room and dining area. There is also a full bathroom (shower only) upstairs.

- 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.

Channel Winds

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Internet

Welcome to your dream island getaway on Chincoteague Island! This waterfront townhouse sits right on the Assateague Channel, serving up jaw-dropping views of the lighthouse that'll make your morning coffee taste even better.

With three bedrooms and two and a half bathrooms, there's plenty of room for the whole crew. The primary en suite bedroom is the real showstopper here, featuring a private balcony that overlooks the water. Imagine waking up, stepping outside, and watching the sun paint the channel gold. Not a bad way to start the day, right?

The outdoor living space is where the magic really happens. Two levels of waterside decks give you plenty of room to spread out, soak up the views, and just breathe. Fire up the gas grill for a seafood cookout while the kids explore, or simply kick back and watch the boats drift by. Life moves a little slower here, and that's exactly the point.

Adventure seekers, this one's for you. Kayaks, a paddle board, and bicycles are all provided, so you can hit the water or cruise the island without packing extra gear. The famous Assateague Wildlife Refuge and its stunning beach are just a short trip away, perfect for spotting wild ponies and catching some waves.

Right around the corner, you'll find Veteran's Memorial Park with a playground, tennis courts, basketball, and more to keep everyone entertained. Need groceries? Island Foods is a quick ride up the road. And for some splashy fun, Maui Jack's Waterpark is nearby too.

This is island living at its finest. Don't let this one slip away, book your island vacation today!

- 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.

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.  

Shady Side

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water access, suitable for a kayak or canoe. The house features two queen bedrooms and a full bath downstairs. Upstairs you'll find two additional bedrooms, one has two twins and the other has a queen bed. There is also a full bath on the second floor. The loft features a futon with a full mattress. The large back porch is equipped with a gas grill and picnic table for your cookouts and crab feasts! 

- 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.

Grey Heron

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Gas Grill
Screened Porch
Internet
Outdoor Shower

Majestic views await you from every room at Grey Heron, a charming raised contemporary located on North Main Street. Enjoy the unparalleled island sunsets from the private dock, spacious screened in porch and dining area, or with it's floor to ceiling windows and numerous cozy seating areas - from anywhere else in the home! Vintage artwork from local artist Hall Lott, known for his cover artwork for the Chincoteague Island Easter & Decoy Festival and Pony Swim posters, adorn the walls at every turn. Plush, cozy furniture in the living area as well as a round-about room featuring stunning 180-degree views of Chincoteague Bay and salt marsh give you plenty of space to enjoy company comfortably. A fully equipped kitchen (range, dishwasher, refrigerator) to prepare meals for family and friends, which is connected to the great room featuring a beautiful working fireplace and natural wooden floors. Grey Heron features 3 bedrooms, each boasting their own private balcony. On the upper level (accessible by the spiral staircase in the great room) you'll find the master bedroom - with the largest balcony, overlooking the sweeping vista of the bay and marsh. A comfortable king sized bed and television, as well as a full bath. The floor to ceiling bay window delivers plenty of natural island sunshine into the bedroom. Downstairs you will find the other two bedrooms - both with queen sized beds, a small balcony, and a cozy sitting area with view of the bay and marsh. Bring your bushel basket and crab right off the dock, then enjoy the bounty of the Chincoteague Bay from the screened-in porch. Bring your kayaks as well and launch them right from the private launch found off the bulkhead on the property. An outdoor shower to hose off after a sandy day at the beach. Plenty of space outside to enjoy family activities, and pet-friendly so bring your furry friends - they love basking in the sun on the dock as much as people do!

- 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.

Farmhouse Sunset

3 Bedrooms
2 Baths
8 Guests
Cape Charles
Town & Country
Gas Grill
Internet

New vacation home listing! Completely renovated and ready to impress, this inviting lower-level three-bedroom, two-bath duplex rental offers comfort, flexibility, and a location that makes everyday living refreshingly convenient. Designed with boaters and coastal enthusiasts in mind, the home sits just minutes from the Chesapeake Bay, giving you quick access to the water without turning every outing into a full expedition.

Inside, the residence feels fresh and updated, with renovations that bring a clean, polished look throughout. The layout is well-suited for a variety of living arrangements, and the duplex configuration adds versatility for those needing extra room. For larger groups or extended stays, there is even the opportunity to rent both the upper and lower portions, creating a practical setup with space to spread out.

Outside, plentiful parking is a standout feature, especially for tenants with multiple vehicles, a boat, or visiting guests. Convenient highway access makes commuting and weekend plans simple, while nearby essentials add to the home’s everyday appeal. The location also offers a practical route toward the Chesapeake Bay Bridge-Tunnel, helping regional travel feel a bit less complicated. Royal Farms is close by for fuel and quick stops, and Food Lion is within easy reach when it is time to stock the kitchen.

Whether you are seeking a comfortable year-round vacation spot, a well-placed coastal retreat, or a flexible rental near the bay, this home checks the boxes with ease and a little style to spare. 

- 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.

Off Belay

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

Welcome! This spacious, luxurious home offers everything you need for a relaxing vacation. Located in the Smugglers Cove community, Off Belay is situated on a small creek, perfect for any nature enthusiast. Upon entering this gorgeous vacation home, you will be enamored with the thoughtful décor and tasteful furnishings. Beautiful hardwood floors lead you to the gourmet kitchen with an expansive kitchen island, including a 5 burner gas range. The living room boasts high ceilings,  plenty of seating,  a wood burning fireplace, and tv as well as access to the large screened in porch and open deck. The first floor also offers a primary queen suite with an attached bath (shower only), and a private den with tv and a queen sleeper sofa. You will also find another full bathroom, washer/dryer and utility sink just down the hall. Upstairs, there are two more bedrooms: a king room with a jack and jill bath as well as a twin room. Walk out to the large deck from the second floor and take in all the views Off Belay has to offer! There is plenty of out door space for entertaining, sitting and relaxation. 

- 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. 

- 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.

Poole's Cove

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Gas Grill
Screened Porch
Internet
Outdoor Shower

Nestled just off Main Street with the water as your backdrop, Poole's Cove is a lovingly curated escape that feels inspired and inviting. Every detail of this thoughtfully decorated home invites you to slow down, breathe deeply, and truly settle in.

The layout is designed for both togetherness and solitude. The primary bedroom suite anchors the main house, while a breezeway connects you to a separate wing with two additional bedrooms and bathrooms — perfect for families or couples who want space to gather and space to retreat.

Step into a large screened-in deck and up to the rooftop deck, where water views, golden sunsets, open skies, and unforgettable stargazing await. When you're ready to unwind indoors, the upstairs office and library is a wonderful place to lose yourself in a good book.

And the best part? Poole's Cove has just undergone a complete top-to-bottom renovation. Brand new kitchen, floors, bedrooms, bathrooms, and furnishings throughout — plus significant exterior updates. The Poole's Cove you've always loved is now better than ever.

This isn't just a place to stay. It's an experience.

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Please note: Due to this home's unique floor plan and open deck railings, it may not be suitable for young children. This is a non-smoking, pet-free property. Linens and towels are available.

- 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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