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A 'Teague of Our Own

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

Welcome to A 'Teague of Our Own! This in-town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated in 'beachy-chic' decor! The living room has abundant seating, complete with a flat screen TV and electric fireplace for those off-season stays. The kitchen is stocked to a chef's standards - there's nothing you won't find including a gas stove, sharp knifes and an herb garden. You will also find a queen sized sleeper sofa in the living room. The three bedrooms are upstairs, and the full bathroom (tub and shower) is downstairs. The enclosed porch with sliding windows allow for room to spread out in any weather. Large carport to keep a vehicle and all your gear under cover. A huge yard for cookouts, games and showering in the outdoor Tiki-shower. This fabulous vacation home truly has it all and has become one of our most popular rental homes. Don't delay; book today! 

- 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 will apply. Pet restriction: one small dog 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.

Pony Dreams

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Gas Grill
Screened Porch
Internet

Welcome to your perfect Chincoteague Island retreat! This brand-new three bedroom, two bathroom house offers the ideal blend of comfort and coastal charm for your vacation getaway. The open floor plan creates a seamless flow between living spaces, making it perfect for gathering with family and friends after days spent exploring this beautiful, picturesque island.

The heart of this home is its fully stocked kitchen, equipped with everything you need to prepare memorable meals using fresh local seafood. Step outside to discover your own screened "crab shack" gazebo – a delightful covered space where you can enjoy meals while staying protected from the elements. Fire up the gas grill for outdoor cooking adventures, whether you're preparing the day's catch or hosting a casual barbecue. 

Location is everything, and this property delivers. Situated close to Maddox Boulevard, you'll have easy access to the island's main thoroughfare leading to pristine beaches. The nearby Bay to Beach Trail access point offers scenic walking and biking opportunities just minutes from your door. Families will appreciate the proximity to Maui Jack's Waterpark for splash-filled fun, while nature lovers can venture to the renowned Assateague Beach to spot wild ponies and enjoy miles of unspoiled coastline.

This thoughtfully designed home provides modern amenities in a relaxed vacation setting. There's plenty of parking, including a space for your boat/trailer (up to 21'). Whether you're planning beach picnics with provisions from your well-appointed kitchen, or simply unwinding after adventures in the comfortable living spaces, every detail has been considered for your enjoyment. Experience the magic of Chincoteague Island living in this exceptional rental home.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises. 

- Linens and towels are included with your reservation.

- 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.

Serenity at Oyster Bay

3 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water View
Gas Grill
Screened Porch
Internet
Outdoor Shower

Aptly named, "Serenity at Oyster Bay" is just what you'll find at this delightful vacation home. Located in the highly-demanded community of Oyster Bay I, you'll enjoy the peaceful, quiet area nestled amongst the tall pines and marsh grasses. The main living area features a fantastic open floor plan; perfect for gathering the family and entertaining. The back of the house features a bright sunroom that looks out over a natural preserve - cozy up with a cup of coffee and a nice book! This home also features 3 bedrooms, 2 full bathrooms (completely remodeled) and has undergone a lot of fresh new upgrades! There's a little sitting deck out back, a screened porch, covered picnic/game area (with cornhole boards), fish cleaning station, and so much more! And, as if that's not enough, there are water views and you're very close to the Oyster Bay Community water access! Don't delay - Serenity at Oyster Bay is sure to book quickly!

- 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

4 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Hot Tub
Internet
Outdoor Shower

Welcome to your serene retreat at Bayside Bliss! This stunning waterfront rental offers a perfect blend of tranquility and convenience, ideal for those who appreciate nature and outdoor activities.

Spanning four generously sized bedrooms and three full bathrooms, this home is a perfect fit for families or groups seeking both comfort and space. Enjoy preparing meals in a fully-equipped kitchen and dine al fresco on the enclosed porch while taking in the breathtaking water views. This space  provides a peaceful spot for morning coffees and cozy evenings alike. You will find one bedroom with a queen size murphy bed, and full bath on the first floor, with all other bedrooms located on the second floor. 

Outdoor enthusiasts will fall in love with the outdoor dock. Whether you’re a fan of boating, fishing, or simply enjoying a sunset over the water, these amenities ensure every day feels like a vacation. The gas grill makes outdoor entertaining a breeze, surrounded by ample deck space that welcomes gatherings under the stars.

The property's location enhances its charm. Nestled just minutes away from essentials, it is conveniently located close to everything you will need to make your vacation enjoyable.

This home not only promises a comfortable and stylish living arrangement but also proximity to local amenities and natural beauty. Embrace a lifestyle marked by peace and relaxation at this Chincoteague charmer. Ready to make it your temporary haven? Contact us today to book your reservation at Bayside Bliss!

- The home does have a hot tub in the enclosed porch but will not be available for this 2024 season.

- 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.

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.

Wildflower

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

Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is a second screened porch overlooking that water from the great room. The second level has a large waterfront master suite with a private balcony, two more bedrooms and another full bath. Close to Memorial Park right across the street from a family restaurant! (Spiral staircase in home, may not be suitable for small children.) For larger groups for family reunions, check out nearby Moon Rising or Herbie's Hideaway!

- 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.

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. An additional fee of $150 per pet will apply. Maximum 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.

Belle of the Bay

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

Truly the "Belle of the Bay", this beautiful custom waterfront home is tucked away at the very tip of one of Chincoteague's most popular residential communities - Oyster Bay I. This means you'll enjoy unobstructed 360 degree water and marshland views from nearly every space in the home. The decor and local art collection alone will "wow" you! Watch the sun rise as you sip your morning coffee from the balcony or screened porch. Enjoy the quiet and privacy as you watch the wildlife that surrounds this fabulous property. The main house features 3 bedrooms, 2 full bathrooms, and an additional loft sleeping area (twin trundle bed). The detached garage features another living area/bedroom (2 Twin beds) that is available for guest use (lower level garage is not accessible by guests). NOTE: Living room fireplace is not functional. 

- 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.

Ms. Kitty's Bayside Bungalow

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

Welcome to Ms Kitty's Bayside Bungalow!  A charmingly remodeled home now available for rent on Eastside Drive. This delightful two-bedroom house offers comfortable living with modern amenities in a serene bayside setting. Each bedroom is furnished with a plush double bed, ensuring a restful night's sleep.

As you step inside, you'll be welcomed by a fresh, contemporary interior that has been newly updated to provide both style and function. The living area is equipped with a Smart Tv and Roku as well as a work desk, perfect for entertainment and relaxation. The kitchen features all the necessary appliances and ample space, making it ideal for cooking and dining.

One of the highlights of this home is its expansive, fenced backyard. It’s an ideal space for pets  and for you to enjoy outdoor activities. The nice deck area offers a perfect spot for barbecues or simply soaking up the calm atmosphere of the neighborhood. Also enjoy a large firepit for smores in the evening hours!

Situated within close proximity to Memorial Park, the location offers convenience with easy access to the boat launch, fishing pier,  playgrounds, basketball and scenic views—perfect for outdoor enthusiasts and families alike.

This rental home captures the essence of convenient and laid-back bayside living. Whether you're looking for a peaceful retreat or a cozy place close to amenities, Ms Kitty's Bayside Bungalow provides an excellent choice for individuals, couples, or small families. 

- 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: 2. Pet Restriction: NO CATS. Breed restrictions apply. (Please inquire). 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.

Dockside

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

Located on the Assateague Channel, this is your chance to watch the ponies from your own deck. A wonderful panoramic view awaits you; to the left is the Assateague Bridge; to right of the bridge is the Assateague Lighthouse and ponies; and to the far right is Tom's Cove and the ocean inlet. Come and fish from your own dock and tie your boat along side! Inside you will find central heat/air, 3 decks, all appliances, gas grill, satellite TV & DVD player and internet access. Enjoy evenings resting beside the wood fireplace (off-season).

Please note: Parking is limited to 2 spaces (this includes a boat/trailer if you are bringing one). Max. boat size for docking is 20'. If alternate parking accommodations are needed, please ask. 

- 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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