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All Done

3 Bedrooms
3 Baths & 1 Half
8 Guests
Chincoteague Island
Water View
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

All Done is located on the popular East Side Road, just minutes from downtown, Maddox Blvd (Beach Road), Memorial Park and the beach on Assateague Island. There are snippet water views of the Assateague Lighthouse and Channel. It is a brand-new home just built in Spring of 2024, and features an open first floor plan joining the kitchen, dining and living rooms into one, as well as a first floor bedroom with full bath. The second floor has 2 more bedrooms including individual full bathrooms, with a walk-in shower in the primary bedroom. There is a spacious laundry room also conveniently located on the second level. The outside of All Done includes a screened porch on the side of the home, and a spacious front porch with ample rockers to enjoy the sunsets over the tree line. There is also a charcoal grill, a large yard for games and parking for up to 4 cars.

- 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. 

- 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.

The Pearl

4 Bedrooms
3 Baths & 1 Half
8 Guests
Cape Charles
Water View
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

Welcome to "The Pearl" - and your next chapter of coastal living in the sought-after Bay Creek community on Virginia's Eastern Shore. This brand new four-bedroom, three-and-a-half-bathroom home is a stunning retreat where modern elegance meets small-town charm, and every detail has been thoughtfully curated for refined living.

Step inside to discover a light, bright, and airy interior that immediately puts you at ease. Professionally decorated from top to bottom, the home showcases a sophisticated aesthetic that blends coastal warmth with contemporary flair. The upscale kitchen serves as the heart of the home, outfitted with premium finishes and designed to inspire both casual meals and memorable gatherings. Generous living spaces flow seamlessly throughout, while serene pond views from the home create a tranquil backdrop you will never tire of admiring.

The spacious primary bedroom offers a private sanctuary, complemented by three additional well-appointed bedrooms that provide ample room for family and guests alike. With three and a half beautifully finished bathrooms, morning routines remain effortless no matter how full the house may be.

Beyond the front door, the Bay Creek community elevates everyday life into something truly extraordinary. Guests enjoy access to world-famous golf courses, resort-style pools, a state-of-the-art fitness and life center, scenic walking trails, and an on-site restaurant. Just a short distance away, the beloved Cape Charles Beachfront awaits with its golden sands and breathtaking Chesapeake Bay sunsets. Stroll through the charming town to explore Central Park, local boutiques, and a vibrant dining scene. Convenient grocery shopping at nearby Food Lion ensures daily errands are a breeze, while the iconic Chesapeake Bay Bridge-Tunnel connects you effortlessly to the greater Hampton Roads region.

This is more than a rental — it is a lifestyle. Book your vacation and experience the best of Eastern Shore living for yourself.

SPECIAL NOTES:

This rental home is NO SMOKING and NO PETS.

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 with 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, paddleboarding, 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.

- 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.

Stella del Mare

3 Bedrooms
2 Baths & 1 Half
10 Guests
Chincoteague Island
Water View
Charcoal Grill
Internet
Outdoor Shower

Stella del Mare - or "Star of the Sea" in Italian - is about as charming as it gets. Located on South Main Street, this beautiful newly-remodeled home has everything you could want in a coastal cottage. Enjoy coffee on the front porch while watching the island come to life in the morning, or sip on a cocktail while waiting for the sun to set. The ground floor features an open floor plan with fully equipped kitchen - gas range, refrigerator/freezer, dishwasher, coffee maker. A beautiful breakfast bar area, as well as dining area. And a beautifully decorated living area with tv. The master bedroom is located on the ground floor featuring a king bed and full bath attached. Another full bath is located on the ground floor as well. On the second floor you'll find two additional bedrooms - one with two full beds, and the other with twin bunks, as well as a comfortable futon. Perfect spot for the kiddos! A comfortable living area in the middle to put a movie on for the kids. There is also a full bath located upstairs as well. Walk downtown for some shopping, then come back to the house and order a cheesesteak from the best sub shop in town - located just across the street. Or, maybe you'll catch a whiff of the oyster fritters frying down at the carnival grounds and walk down to sample one. Go ahead, you're on island time! Newly added patio on the back with lovely seating area to enjoy your meals al fresco, or just to sit and chat and enjoy the sunshine. You're sure to find plenty to put a smile on your face at Stella del Mare - the star of the sea. Floor plan: Downstairs (main level) features an open living/dining room and kitchen with breakfast bar. The master bedroom with connected bathroom (tub and shower) is also downstairs. Upstairs there's an open living room/sitting area, a full bathroom (with separate shower and tub) and two more bedrooms. One bedroom features a Double and Queen bed, and the other bedroom features a bunk bed (2 Twins) with a pull-out Twin trundle, as well as a Queen size futon. There is a portable Pack-n-Play crib and high chair for guest use as well.

 If you're traveling with a larger group but like the separate of "your own place", check out 'Stella Della Baia' ! Book both homes and receive a 5% discount off of each!

- 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.

Cape Charles Cottage

4 Bedrooms
2 Baths & 1 Half
10 Guests
Cape Charles
Pet Friendly
Gas Grill
Internet
Outdoor Shower

Welcome to Cape Charles Cottage in the historic district! We are 6 blocks to the beach and 4 blocks to Mason Avenue (shops, restaurants).Whether on foot or by golf cart, getting around town is a breeze! We can host up to 10 guests with 4 bedrooms and a bonus room with a daybed/trundle that pulls to side by side twins. One bedroom has an ensuite bathroom and the others share a hall bath with a tub/shower. The kitchen is fully equipped!

Our home is designed as a family getaway so you can pack light! Parents will appreciate convenient amenities like a high chair, full sized crib, kids books, games and toys. But our house isn't just for kids. Adults can enjoy our 2 stand up paddle boards, beach chairs, plus a grill, fire pit, and Adirondack chairs in our big, shady backyard. Rinse off in the outdoor shower after a day at the beach! We also provide two beach cruisers for your use as well as a kid's bike.

Although our house has a cozy cottage feel, many people have commented on how spacious it feels, with plenty of room for everyone to spread out. In terms of the bedroom setup, there is a bedroom on the main floor with a queen bed (note you will need to go upstairs for the shower/bath). On the second floor, you'll find our "family suite" a bedroom with an ensuite bathroom and a connected bonus room with a daybed that can fold into 2 side by side twins (ideal for kids)! Also, on the second floor are two additional bedrooms, one with a queen bed and one with a king. There is another bathroom on the second floor with a tub/shower combo. There is a powder room on the main level by the kitchen.

With two smart TVs you can easily access all your favorite streaming apps — one in the living room and one in the kid's room upstairs. You'll find smart speakers throughout, allowing you to choose a soundtrack for your beach week. Easily check in with our smart lock accessed via passcode.

Walk, bike or golf cart around town to shops, bakeries, a park with a playground that hosts summer concerts, restaurants, a candy store, a distillery, a bookstore, a shaved ice shack, a cidery, and of course the beautiful beach! With its gentle waves and soft sand, this beach is ideal for relaxing. Make sure you don't miss the sunset, it's gorgeous here. Custom, 6-seater golf cart are available for convenient transportation throughout the community complete the ultimate experience (additional fee of $100 per day or $600 per week required).

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly for an additional fee per pet. The 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.

Sunrise/Sunset

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Town & Country
Gas Grill
Internet

Looking for an island home that won't drain your savings? This two-bedroom, two-and-a-half-bathroom townhouse delivers comfortable Chincoteague Island vacationing with a price tag that actually leaves room for ice cream cones and beach days.

The heart of this home is its standout four-season room, a bright and breezy spot built for year-round enjoyment. Curl up with a book in the dead of winter or throw the windows open when the salt air calls — either way, you'll find yourself drawn back to this cozy corner again and again. An electric fireplace adds a flicker of warmth to chilly evenings, perfect for unwinding after a day of island wandering.

Both bedrooms sit upstairs, tucked away from the main living areas for a little extra peace and quiet when it's time to rest. Step outside and you'll discover a fenced yard, ideal for letting pets roam, hosting a casual cookout, or simply claiming your favorite lawn chair under the open sky.

Location? You've hit the jackpot. Veteran's Memorial Park is practically next door, complete with a playground, courts, and plenty of green space. The annual Carnival is just around the corner for summertime fun, while Island Foods handles grocery runs in a flash. When adventure calls, Maui Jack's Waterpark and the legendary Assateague Beach — wild ponies included — are a short hop away.

Affordable, comfortable, and perfectly positioned. What are you waiting for?

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Pets (dogs only) are permitted with an additional pet fee of $150 per pet. 

- 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.

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.

Delmarva

1 Bedroom
1 Bath
2 Guests
Cape Charles
Pet Friendly
Internet

Nestled in the heart of historic Cape Charles, this exquisite one-bedroom condominium embodies coastal living at its finest. This newly constructed residence represents the pinnacle of architectural refinement, where simplicity meets sophistication in a harmonious blend of form and function.

Step into a meticulously designed living space where each detail has been thoughtfully curated. The living room features a fireplace and large TV, while the bedroom showcases a sumptuous king-sized bed, large TV and private balcony overlooking downtown - all complemented by a custom bathroom featuring splendid tile work. Truly a sanctuary of tranquility after a day of bayside adventures.

What truly distinguishes this property is its coveted upper-level position, affording the most captivating vistas of both the charming downtown area and the magnificent Chesapeake Bay beyond. As the golden light of sunset bathes the water in amber hues, you'll appreciate the privileged perspective this elevation provides.

The crown jewel of this condo is undoubtedly the rooftop terrace — an oasis where you can sip morning coffee or evening cocktails while overlooking the shimmering waters. The full wet bar sheltered beneath an elegant pergola makes entertaining a delight rather than a duty. One might say it's the perfect spot to raise a glass to coastal living without raising your stress levels!

The unparalleled location places you mere steps from Cape Charles' most coveted attractions. Stroll to boutique shops where local artisans display their crafts, savor culinary delights at nearby restaurants, or indulge in handcrafted spirits at Cape Charles Distillery. For sweeter cravings, premium ice cream awaits just around the corner.

The pristine beach, with its gentle waves and golden sands, lies just a few blocks away. No need to concern yourself with traffic. Similarly, the picturesque harbor invites leisurely promenades as boats gently rock against the backdrop of a painted sky.

This remarkable vacation home doesn't merely offer accommodations; it presents a lifestyle where luxury meets location in perfect equilibrium. Come and see for yourself!

PLEASE NOTE: 'Delmarva' 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.

- This property is pet friendly with an additional fee of $150.  All pets must be disclosed prior to arrival. Only 1 small dog is permitted, less than 50 lbs. 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.

Salty Oyster

5 Bedrooms
6 Baths
14 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Internet

Welcome to the crown jewel of Chincoteague Island vacationing! This completely renovated five-bedroom, six-bathroom home offers a rental experience that transcends the ordinary, delivering the kind of coastal luxury that transforms a vacation into a lasting memory.

Every detail of this stunning home has been thoughtfully reimagined from the ground up. Floor-to-ceiling windows flood the main rooms with natural light and frame what are arguably the best views on the island. Rise each morning to gorgeous sunrises painting the water in shades of gold and amber — a private spectacle that never grows old, though you might find yourself setting your alarm earlier just to catch every moment.

The open great room serves as the heart of the home, seamlessly connecting the living, dining, and kitchen areas into one magnificent gathering space. Top-of-the-line appliances, including a wine fridge and ice maker, outfit the kitchen, making meal preparation a genuine pleasure rather than a chore. Whether you are hosting an elaborate dinner for the entire group or simply enjoying a quiet morning coffee, this space accommodates every occasion with effortless elegance.

Each of the five bedrooms features its own private bathroom, ensuring every guest enjoys personal comfort and privacy throughout their stay. Spacious and expansive decks extend the living areas outdoors, providing ample room for relaxation, alfresco dining, and soaking in the island atmosphere.

Nestled within the popular Oyster Bay I neighborhood, this home places you in an enviable position to explore everything the island has to offer. Nearby attractions include the scenic Island Nature Trail for peaceful walks, the beloved Island Creamery for indulgent treats, and Maui Jack's Waterpark for family-friendly thrills. The pristine shores of Assateague Beach, home to the island's famous wild ponies, await just a short drive away.

This exceptional vacation home represents Chincoteague Island living at its absolute finest. Book your stay and see what it's all about - there's no doubt you'll want to return time and time again!

- 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.

Sunset Dreams

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Internet
Outdoor Shower

If you're familiar with the island you know that the best sunsets can be found on Main Street, and the sunsets waiting for you at Sunset Dreams (located on south Main Street), are NO EXCEPTION. A luxury waterfront townhome overlooking Chincoteague Bay, offering 3 bedrooms and two and a half baths - with a private pier, it's the perfect place to unwind and get on "island time". On the lower level you'll find the open area kitchen and dining area that features a stunning view of Chincoteague Bay and the salt marsh - that has everything you'll need to enjoy the various fresh catches waiting for you just off of the dock, or at our local seafood markets. A comfortable living area also boasts a beautiful waterfront view, with sliding doors that open up to a lovely little sitting porch - perfect for taking in the sunset with a cocktail without having to go too far. There is also a bedroom downstairs with two twins, a half-bath powder room, and a beautiful large sunroom/sitting area - great for sneaking away for a minute to get some work done or curl up with a good book. On the upper level you'll find the master bedroom with a queen bed, a full bath, and a beautiful waterfront view. Another bedroom with a queen bed is upstairs as well. A full bath can also be found upstairs in the hallway, and both bedrooms have televisions. Full sized washer and dryer for washing all those beach towels and bathing suits. You have full access to the dock across the street, so bring your fishing poles and crabbing gear (or visit Captain Steve's on Maddox Blvd to get what you need!). You're a quick two-minute ride to downtown to restaurants and the grocery, or an easy bike ride to the carnival or the sub shop to grab a quick bite to eat. Come stay with us and enjoy sweet dreams at Sunset Dreams, and bring along your favorite four-legged friend, as this rental is dog- friendly! Need more space? Rent "Saltwater" right next door! Note: The pier is shared with the other 2 adjoining townhomes.

- 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: two pet max.

- 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 Lookout

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water View
Charcoal Grill
Internet

This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run and play, or fish and crab at the waterfront Memorial Park. The first floor is an open room consisting of the kitchen, dining area and living room (with queen sleeper sofa). You'll also find a full bath on this level. The second floor offers a queen bedroom with a private deck that has unlimited views of the Assateague Channel! The second bedroom has two twin beds and you'll find another full bathroom upstairs as well. Come and see for yourself! (Waterfront areas, dock, pier and playground area pictured are public property/Memorial Park.)

- 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.

Bayside Bliss at Cape Charles

3 Bedrooms
2 Baths & 1 Half
10 Guests
Cape Charles
Gas Grill
Internet
Outdoor Shower

Welcome to your idyllic retreat in the charming coastal community of Cape Charles. This brand new three-bedroom, two-and-a-half-bathroom residence offers the perfect blend of comfort and sophistication for your Eastern Shore getaway.

Step inside to discover thoughtfully designed living spaces, including a spacious living room and a versatile loft area upstairs (with Queen Sleep Sofa) —perfect for a quiet reading nook, or entertainment zone. The convenience of a first-floor primary bedroom suite means accessibility and privacy for the discerning tenant.

The backyard presents a picturesque setting with a scenic pond, offering tranquil views and a peaceful atmosphere for morning coffee or evening relaxation. Imagine watching herons glide across the water as the sun sets—nature's own entertainment system!

The stunning Cape Charles Beachfront is nearby, providing endless opportunities for seaside adventures. After a day of exploration, return home or indulge in a delicious meal at the local restaurants. This exceptional rental property offers more than just a place to stay—it's a gateway to the coastal getaway you've been dreaming about.

- 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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