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Waterman's Daughter

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Water View
Pet Friendly
Charcoal Grill
Internet

We are excited to introduce Waterman's Daughter! This stately townhome is located on a quiet lane off of East Side Drive. The first floor of the home features two bedrooms, both featuring full attached baths! A full size washer and dryer are conveniently located off the hall in between these bedrooms. As you make your way to the second floor of the home, you are greeted by a bright living space featuring a flat screen TV, fireplace, large windows, and doors that lead you out to the second floor balcony that features a table for two with a view. Right beyond the dining area of the home, you will find the fully equipped kitchen that features additional seating for three at the kitchen bar, a stove top oven, microwave, and dishwasher. The large Master bedroom is on the second floor of the home and features yet another full attached bath and wall-mounted flat screen TV. There's even a shared waterfront area - perfect for launching your kayak or canoe. This home is truly the perfect setting for your next Chincoteague Island vacation; clean, relaxing, and accommodating! Call us or book online today!

- 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.

Blue Pointe Bayside

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

Spectacular waterfront home on the end of a cul-de-sac! Bright, airy and immaculate! Four decks, including one off of the stunning 2nd floor Private Master Suite. Dramatic cathedral ceiling in the cozy, waterfront living room. A screened porch to host an outdoor dinner. Central heat for those off-season stays, and Central A/C for the summer stays, make this the perfect vacation house all year 'round. A sunny, well equipped, eat in kitchen for the gourmet cook. Down-draft cook top and gas grill; perfect for any meal. Beautiful sunsets on the Chincoteague Bay - Water views from every room! Large, hot water outside shower and an oyster shell path to the water so you can easily walk out to the bay to crab, fish and kayak.

- 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.

Vast Views

2 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water View
Pet Friendly
Boat Dock
Pool
Internet

Welcome to your perfect coastal getaway in charming Chincoteague Island! This newly remodeled townhouse offers the ideal blend of comfort and modern amenities, featuring two cozy bedrooms and three full bathrooms as well as an open floor plan perfect for entertaining! Step into a space where everything sparkles with newness, from the stylish fixtures to the thoughtfully placed flat-screen TVs in every room. The innovative touches, such as bathrooms equipped with cutting-edge built-in Bluetooth speakers, make this home perfect for both relaxation and entertainment.

The location couldn't be better for beach lovers and adventure seekers. Step outside to enjoy exclusive community amenities like a swimming pool and a pier with direct water access to Assateague Channel. Try your hand at fishing or crabbing, or tie up your boat - there’s no better way to end your day than with mesmerizing water and lighthouse views right from your vacation home! The community pool provides a refreshing escape on warm summer days, while the nearby Memorial Park offers tennis courts and a playground for your enjoyment.

The East Side location could not be more ideal - when you're not in the mood to cook, local restaurants are just a short stroll away, serving up fresh seafood and coastal favorites. The area's attractions are sure to keep you entertained, with Maui Jack's Waterpark and the pristine Assateague Beach both within easy reach. Nature lovers can explore the famous wild ponies and abundant wildlife that make this island so special.

This townhouse isn't just a rental – it's your piece of paradise that offers the laid-back coastal lifestyle that Chincoteague is famous for. Whether you're seeking a peaceful retreat or an adventurous beach vacation, this home delivers the best of both worlds.

This pet-friendly home also offers the option to rent neighboring units, making it ideal for larger groups or family gatherings! Make this brand new townhouse your sanctuary on Chincoteague Island, embracing a blend of comfort, convenience, and natural beauty all around. Your island lifestyle awaits!

- 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.

Casa del Mar

5 Bedrooms
4 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Hot Tub
Internet
Outdoor Shower

Casa del Mar - "House by the Sea" - is your home away from home... at the beach! Located in the heart of downtown Chincoteague Island, this grand home has been lovingly maintained and is conveniently situated within walking distance to the waterfront park, boutique shops, restaurants, movie theater and coffee shops! Casa del Mar is one of our newest vacation rental offerings, and we know you'll love it! The spacious, open floor plan features a family room and kitchen, as well as a formal living room and plenty of outdoor space. There's a master bedroom en suite, and the bathroom features a tiled shower and jacuzzi tub. Outside you'll find the perfect backyard, complete with a grill, outside shower. Perfect for relaxing in the evenings after a long day at the beach! And you can even bring the 4-legged family members as well! Don't delay; this one will book quickly! Floor Plan: Downstairs features the living room, family room, kitchen w/ dining area, dining room, master bedroom (King bed & Futon) and full bathroom (shower only). Upstairs features 4 bedrooms - one with a King, one with 2 Queens, one with a Queen, and another with a Queen. The King bedroom and 2 of the Queen bedrooms have attached bathrooms (tub & shower). There is a 3rd upstairs bathroom w/ tub & shower off of the hallway.

- 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.

The Pearl

4 Bedrooms
3 Baths & 1 Half
8 Guests
Cape Charles
Water View
Gas Grill
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 and golf cart 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, 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.

Sunrise View

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

**Island Living at Its Finest — Where Sunrises Steal the Show**

Welcome to the most breathtaking views Chincoteague Island has to offer. Nestled in the sought-after Oyster Bay I Community, this stunning three-bedroom, three-bathroom rental home is a haven for those who crave inspiration from the natural world. If you're an artist, writer, creator, or simply someone who finds peace in golden-hour magic, this is where you belong.

Step inside to discover a thoughtfully designed living space that includes a comfortable living room and an additional den — perfect for curling up with a good book or sketching the marshland views that stretch endlessly beyond your windows. Feeling playful? Challenge your guests to a round of bumper pool, because every retreat deserves a touch of friendly competition.

The real magic unfolds across multiple levels. Climb the spiral staircase to the third-level tower room, where panoramic vistas will leave you utterly speechless. Gorgeous sunsets paint the sky in hues you didn't know existed, and you'll find yourself reaching for a camera — or a canvas — night after night.

Outdoor living shines here with spacious decks ideal for entertaining and a screened porch complete with a ceiling fan, offering bug-free relaxation while the island breeze does the rest. It's the kind of space where conversations linger and worries disappear.

Beyond the home, adventure awaits. Explore the nearby Island Nature Trail for serene walks through coastal landscapes, catch waves at Assateague Beach where wild ponies roam, or bring the family to Maui Jack's Waterpark for splashing fun on warmer days.

This is more than a rental — it's an experience that feeds the soul. Reach out today to secure your island escape and experience these legendary sunrises over the bay.

- 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.

Cedar Cove

3 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Waterfront
Gas Grill
Internet
Outdoor Shower

Tranquility meets you at every turn at Cedar Cove, a custom-built waterfront home nestled amongst the pines in the Oyster Bay I community. The open floor plan allows for a bright and airy atmosphere in the common areas downstairs - an open living room with a gas fireplace to warm a chilly evening, and a bright and cheery fully-equipped kitchen. The primary bedroom is also found on the ground floor, with a queen bed and bath, flat-screen television, and private balcony overlooking the backyard and waterfront view. The bathroom also has an entrance from the entrance hall of the house, allowing it to act as a bathroom for guests downstairs as well. Upstairs you'll find a game loft complete with a foosball table, a futon, and plenty of board games to keep the kids busy on a rainy day. Two additional bedrooms are also upstairs, one with two full size beds and another with a queen size bed - both have televisions and balconies as well. A newly-remodeled full bath is also located upstairs off the loft area as well. Outside you'll find ample space for plenty of outdoor enjoyment with the family - a spacious deck with outdoor seating and dining areas, a firepit with comfortable Adirondack chairs, and an outdoor shower to rinse off the sand after a long day at the beach. Located in a quiet private community just off the "beaten path" - all the amenities Chincoteague has to offer are just minutes away on the bike or in the car. Bring your kayaks and launch right from the small dock located on the property, or grab a pack of chicken necks at the grocery store and catch a few crabs - round out the meal with a sack of oysters from Gary Howard's market just up the street (if all else fails he sells crabs at a reasonable price too). Then take the time to gather with family on the porch to enjoy the bounty the island has to offer - all from the comfort of Cedar Cove here on Chincoteague Island.

- 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.

Oyster Catcher

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet

Welcome to Oyster Catcher! This home offers a prime location, beautiful views and a deep water dock (6 feet at low tide)!  We encourage you to sit and relax on the large screened porch and enjoy all nature has to offer. Upon entering the home from the side door, you'll be greeted by the the fully equipped kitchen that provides all the essentials for meals at home, while overlooking some of the most beautiful views the Island has to offer. The living room does not lack views either- sit and relax while opening one, or all four, of the large panoramic folding doors that span across the kitchen and living area. Enjoy the sounds of nature or feel the cool salt air breeze. There is a first floor bedroom, with a full size bed and a separate full bath (tub/shower combo) - you have your own access to the screened porch from the first floor room.  The living room also has a queen sleep sofa.  Upstairs you will find two more bedrooms, one with two twins and another with a full. All bedrooms showcase breathtaking views of Deep Creek. Venture outside to the private guest cottage that holds much history from one of the Islands most plentiful seafood shacks. The guest cottage features a queen bed and full bathroom with shower, as well as a floating twin bed. Drop a line or a crab pot at the end of your private dock- maybe you will even get to enjoy a fresh catch for dinner! Oyster Catcher offers a private setting with bountiful plants and greenery, plenty of yard for whole family including your fur babies!  Other amenities include a gas grill and WIFI.

- 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.

 

Sunset on the Rocks

4 Bedrooms
3 Baths & 1 Half
14 Guests
Cape Charles
Waterfront
Pet Friendly
Internet

Experience coastal living at its finest in this stunning 4-bedroom, 3.5-bathroom abode nestled within the prestigious Butler's Bluff community of Cape Charles, VA. Boasting an impressive 4,900 sq ft of interior space, this home offers a perfect blend of luxury, fun and comfort.

The heart of this home lies in its expansive windows that frame mesmerizing views of the Chesapeake Bay. The interiors are thoughtfully designed to maximize both comfort and elegance, featuring a dedicated game room and a serene lookout sitting area ideal for enjoying breathtaking sunsets or a quiet morning coffee.

Outdoors, the property exhibits meticulously maintained landscaping that harmonizes with its secluded setting. Entertain or simply unwind in the outdoor seating areas that provide a private beach feel without leaving your home. The charm of this residence is enhanced by its proximity to downtown Cape Charles, where you can indulge in local restaurants, eclectic shops, tasty ice cream parlors, and entertaining mini-golf options, all just minutes away.

Pet owners will appreciate the pet-friendly environment, ensuring every family member is catered for in this idyllic locale.

This home not only promises a peaceful and picturesque setting but also offers practicality with its generous room sizes and versatile living spaces. Whether it’s hosting gatherings, family game nights, or simply enjoying the solace of the bay, this escape provides the perfect setting.

- Linens and towels are included with your reservation

- No smoking is permitted on the premises. 

- This home is pet friendly for an additional fee of $200 per pet. Maximum of two dogs; 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.

zLT - 5457 Warren Street

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Pet Friendly
Screened Porch
Internet

Discover your perfect island getaway at this delightful four-bedroom, two-bathroom house nestled in the peaceful Richardson's Landing community on Chincoteague's quiet north end. This comfortable home offers everything you need for a relaxing vacation, whether you're planning a family retreat or a fun-filled adventure with friends.

Step outside to your own private screened porch, where morning coffee tastes better and evening conversations last longer. The spacious yard provides plenty of room for outdoor games, barbecues, or simply soaking up the island sunshine. Inside, you'll find clean, comfortable living spaces that make it easy to unwind after busy days exploring the area.

The location puts you perfectly positioned to enjoy both tranquility and excitement. When you're ready for some splashing fun, Maui Jack's Waterpark is just a short drive away. Nature and beach lovers will appreciate the nearby Chincoteague National Wildlife Refuge, home to the famous wild ponies and incredible birdwatching opportunities. For your convenience, Island Foods Great Value grocery store ensures you'll have everything needed for home-cooked meals.

This newly available vacation rental combines the best of island living with modern comfort. You'll love the peaceful setting that still keeps you close to all the attractions that make Chincoteague special. From wildlife watching to beachcombing, your island adventure starts here in this welcoming home that's ready to become your home away from home.

- 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.

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.

Sunset Bay Villa 206

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Charcoal Grill
Pool
Internet

Villa 206 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with private luxury bath and private exit to the waterside balcony. Villa 206 will sleep 8, and there are a total of 4 TVs. A laundry room within the unit houses your washer & dryer. Your stay also includes use of the Sunset Bay marina, pool and fitness areas. Come. Enjoy! Note: This property does not have a boat slip, however, use of the marina is included. 7-night minimum stay is required during all seasons.

- 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.

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