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Escape at Deep Hole Hideaway

2 Bedrooms
1 Bath
6 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Internet

Enter a world of tranquility at Deep Hole Hideaway! Need a break from the daily grind? We've got you covered! Our chic and well-equipped living space will make you feel right at home. And when your tummy rumbles, our kitchen is your culinary sanctuary. Two snug bedrooms await you, furnished with a Queen bed, a Twin daybed, plus a sleeper sofa for your whole posse! The elegant and refreshing décor will overwhelm you with happiness as soon as you step through the front door!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. Cats are considered on a case by case basis. 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.

Beach Bettie's

3 Bedrooms
1 Bath
6 Guests
Smith Beach
Waterfront
Internet
Outdoor Shower

Discover coastal living at its finest in this enchanting three-bedroom cottage nestled along the pristine shores of the Chesapeake Bay. This waterfront retreat offers an unparalleled opportunity to experience the serene beauty of Virginia's Eastern Shore while enjoying the perfect blend of comfort and bayside charm.

The thoughtfully designed interior features three inviting bedrooms and a full bathroom, creating an ideal space for multi-seasonal getaways. Water-facing windows throughout the home frame spectacular views of the bay while allowing natural light to cascade through the living spaces, creating an atmosphere of warmth and tranquility.

Step outside onto your private slice of paradise, where meticulously maintained landscaping creates a picturesque setting for outdoor entertainment and relaxation. Multiple seating areas have been strategically placed to maximize the breathtaking vistas, making it the perfect spot to unwind while watching the sun paint the sky in brilliant hues during the legendary Chesapeake Bay sunsets.

This exceptional property's location offers the best of both worlds – peaceful seclusion with convenient proximity to beloved local attractions. Just minutes away, you'll find the renowned Cape Charles Beach, where soft sands and gentle waves await. The historic downtown district, with its charming boutiques, restaurants, and galleries, is also within easy reach. Nature enthusiasts will appreciate being near the Savage Neck Dunes State Natural Area Preserve, offering pristine hiking trails and unspoiled coastal wilderness.

Whether you're seeking a peaceful year-round residence or a memorable vacation retreat, this bayside haven provides an extraordinary opportunity to embrace the coveted coastal lifestyle. The combination of waterfront splendor, thoughtful design, and prime location creates an unmatched living experience on Virginia's celebrated Eastern Shore.

Special Note: The loft room is accessible by a ladder and, because of such, is not an advertised sleeping area. There is a Full-size bed in the loft, however, no linens are provided for this bed. 

- 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 Duty

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Pool
Internet

Off Duty offers 3 bedrooms, 2 bathrooms, a large screened porch, front deck with bay views, and a large outdoor space for your enjoyment. Bring your fur babies along, because this home is pet friendly! Upon entering the home, you will find yourself in awe of the large open floor plan, boasting high ceilings and tons of waterfront views for your enjoyment. Downstairs you will find two bedrooms, one with a queen sized bed and deck, as well as a bedroom that has a full sized bed and a twin bunk bed. Upstairs is an additional bedroom with a queen bed and full bath, along with a sitting area looking over the downstairs living space. Don't feel like sitting inside? Go out to the large screened in porch and enjoy the sounds of nature, or sit downstairs under the home one afternoon and enjoy some fresh catch on the picnic table while enjoying a beverage at the tiki bar. Got a boat? No problem! Off duty has a boat lift and ladder at the dock! The Captain's Cove community offers 3 pools (2 outdoor & 1 indoor), tiki bar, Marina Club and restaurant, 9-hole golf course, kids playground, dog park and more! (with fee) And you're only 20 minutes from Chincoteague & Assateague Islands (the beach), and 30 minutes from Ocean City, MD (boardwalk & amusements).

- No smoking is permitted on the premises.

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 4.  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.

-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. 

Island Thyme

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Gas Grill
Hot Tub
Internet
Outdoor Shower

There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-in kitchen and dining area, and a huge wrap-around deck -- perfect for enjoying the quiet, peaceful setting. The many extras include a hot tub (on back deck), and Foosball table. And, it is conveniently located at the back of the Chincoteague Carnival grounds, so you can walk to the carnival (July only) on those warm summer nights! So come and stay a while; you're on Island Thyme now!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Pets are not 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.

The Lighthouse

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Waterfront
Boat Dock
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

Nestled in the picturesque Captain's Cove community, this exquisite three-bedroom, two-bathroom waterfront residence represents the pinnacle of sophisticated coastal living. The stunning new construction boasts an airy, well-conceived open floor plan that seamlessly blends indoor refinement with the serene beauty of unobstructed bay views.

The chef's kitchen stands as a culinary sanctuary, where premium finishes and state-of-the-art appliances await the discerning home cook. In the evening hours, the ambient glow of the fireplace creates an atmosphere of unparalleled comfort and tranquility. For entertainment aficionados, each bedroom features a Smart TV—including the primary bedroom suite.

Perhaps most alluring is the property's 4-season room and direct bulkhead access to the bay, with boat dockage available for nautical enthusiasts. One might say this home doesn't just offer a lifestyle—it launches one.

The distinguished community amenities elevate everyday living to resort-quality experiences, featuring both indoor and outdoor swimming pools, a fitness facility, and an on-site restaurant. The adjacent marina and golf course create a playground for those with a passion for waterfront and fairway pursuits.

This exceptional property affords the advantage of being merely 20 minutes from the wild horses and pristine shores of Chincoteague Island, with the Assateague Island National Seashore's and beach just beyond. For those seeking more vibrant diversions, Ocean City's renowned boardwalk and attractions await just 30 minutes away, while Maui Jack's Waterpark offers family entertainment nearby. As one of Coastal Shore's newest offerings, don't sleep on this one. It will book quickly!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- No pets are permitted on the premises.

- 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.

- 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.

Cockleshell Cottage

3 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage! This modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs features 2 more bedrooms (Double and Double/pull-out Twin trundle), and a full bathroom. Cockleshell Cottage is handicap accessible. Relax and enjoy the breeze on the open front porch or back screened porch. Call us today; this home books fast!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. Pet Restriction: Small dogs only, under 35 lbs. NO CATS. 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.

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.

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

This property is pet friendly. An additional fee of $200 per pet will apply. Maximum pets allowed: 2. 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 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, 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.

Misty's Thicket

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Charcoal Grill
Screened Porch
Internet

Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends. Upstairs, you find a great master bedroom with en-suite, a full bathroom off the hallway, and a second bedroom that features a bunk bed and a queen size bed that looks out onto the second-level screened in porch affording amazing Chincoteague Island views.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pets are not 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.

Oyster Shack

3 Bedrooms
2 Baths & 1 Half
8 Guests
Cape Charles
Town & Country
Pet Friendly
Internet
Outdoor Shower

Introducing the newest gem in Cape Charles! Perfect for those seeking a serene retreat, this charming vacation rental boasts three cozy bedrooms, including a spacious primary bedroom, complemented by two and a half well-appointed bathrooms. Nestled in the heart of town, this delightful home invites comfort and exudes modern elegance.

Step inside to discover a beautifully crafted layout where each square foot is maximized for enjoyment and ease. You'll love the convenience of your own peaceful backyard, ideal for morning coffees and evening relaxation. Plus, it’s a pet-friendly haven, so your furry friends can join in on the fun!

Staying here, you're seconds away from sinking your toes in the beautiful beach, ensuring endless days of sun-soaked adventures. Need a break from the sun? Dive into the refreshing experiences available at the nearby at Cape Charles Mini Golf!

For those who love cooking with fresh ingredients, the local Beach Market is just a short trek from your doorstep, making it nearly effortless to gather necessities for a spontaneous beach picnic or a cozy family dinner.

Whether you’re in for a weekend getaway or a longer relaxing stay, this house is more than just a place to stay—it’s the backdrop for your next chapter of cherished memories! Ready to kick off your sandals and stay a while? This Cape Charles beauty is waiting to welcome you! 

 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 4. Pet restriction: NO CATS. 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.

 

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. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. Pet Restriction: NO CATS. 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

Egret's Walk

2 Bedrooms
1 Bath
5 Guests
Chincoteague Island
Town & Country
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

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 Value 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. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. 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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