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Shreiner's Tradition

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet
Outdoor Shower

As one of our newest vacation rental offerings, we're pleased to be have this downtown charmer! Shreiner's Tradition is a renovated 2+ bedroom home located just outside the downtown area. Enjoy walking to restaurants, shopping, ice cream and the movie theater! This home features an eat-in kitchen, 2 living room/sitting areas, 2 bedrooms upstairs (each has a double bed) and a walk-through room with bunk beds. Not to mention the great front porch - you'll enjoy mornings and afternoons sipping coffee or relaxing after the beach!

- 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 pet pet. All pets must be disclosed prior to arrival. Pet restriction: 2 dog limit and 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.

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 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.

Donovan's Reef

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

Charming Chincoteague coastal cottage doesn't even begin to describe this place, but it's a start. Cheery, bright, and colorful - with some form of island history gracing every nook and cranny. Find the perfect mix of old and new in this unique home. Close enough to the main drag on Maddox Boulevard and Main Street - but out of the hurly-burly here on Ocean Boulevard. Wake up a few minutes before everyone else and head across the street to get fresh donuts from Mister Whippy or chocolate croissants from Amarin to surprise everyone with. You'll be the hero for the day, until someone else brings home oysters that night. Oh, and bring your furry friends along, because this one's PET FRIENDLY! This property features lots of nooks for sleeping spaces - a loft upstairs, featuring skylights that let the bright island sunshine flood in. Up here you'll find a cozy king size bed in one room, and two twins in another, with a full bath that features a gorgeous tiled stand up shower. Downstairs you'll find two more bedrooms - one with two twins, and the other with a king. Three different comfortable living areas, one of which is an outdoor sunroom - and that room has doors that connects to the downstairs king - in addition to the main living area. Small backyard area for letting the puppies play or eating lunch outside at the picnic table. The retro mid-century kitchen has everything you'll need to prepare that island seafood dinner with what you catch down at the town dock, and a lovely dining area to enjoy it as a family. Donovan's Reef is located in the heart of downtown Chincoteague, allowing you an easy walk to all the shopping the island has to offer. Stop by Chincotiki on your way home and grab an orange crush or two!

- 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.

Sand Dala

5 Bedrooms
3 Baths & 1 Half
12 Guests
Cape Charles
Gas Grill
Pool
Internet
Outdoor Shower

Discover sophisticated coastal living in this brand new five-bedroom, three-and-a-half-bathroom home that seamlessly blends modern elegance with comfortable functionality. This thoughtfully designed residence features an interior designer's curated touch throughout, creating spaces that are both chic and inviting for everyday living.

The home showcases contemporary finishes and stylish furnishings that complement the coastal setting perfectly. Each room has been carefully appointed to maximize comfort while maintaining a refined aesthetic that speaks to discerning tastes. The primary king bedroom downstairs, with four additional bedrooms upstairs (king bedroom upstairs is also ensuite), provide ample space for family and guests, while the three full bathrooms and powder room ensure convenience for all guests. And, to sweeten the deal, a GOLF CART is included at no additional charge!

Located within the prestigious Bay Creek Resort community, residents enjoy exclusive access to an impressive array of amenities that rival the finest vacation destinations. Take advantage of multiple swimming pools for leisure and exercise, or spend peaceful afternoons on the private beach overlooking the Chesapeake Bay. The full-service fitness center supports an active lifestyle, while miles of scenic nature trails offer opportunities for hiking and wildlife observation. The community's private dining options provide convenient culinary experiences without leaving the neighborhood.

For those seeking broader cultural experiences, some leisurely shopping, or a movie at the timeless theater, historic downtown Cape Charles lies just minutes away.  Visit charming shops, restaurants, and local attractions that celebrate the area's rich maritime heritage.

This exceptional rental opportunity combines the luxury of resort-style living with the comfort of a thoughtfully designed home. Whether you're seeking a peaceful retreat from city life or an active coastal lifestyle, this property delivers an unparalleled vacationing experience in one of Virginia's most desirable waterfront communities.

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 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.

Mermaid Crossing

3 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Internet
Outdoor Shower

Comfortable home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2 full baths, well-equipped kitchen, dishwasher, washer/dryer, outdoor shower, 1-car garage, Direct TV, wireless internet, DVD, BBQ grill, 4 adult beach cruisers (bring your own helmet), 2 kayaks, crab traps and net, games, books, puzzles, and some beach gear!

- Linens and towels are included with your reservation.

- No smoking is 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.

Joint Venture

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Water View
Pet Friendly
Internet

Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll to Maddox Blvd (Beach Road) and enjoy ice cream, mini golf or any of the shops & restaurants. Bike or drive to the beach! Joint Venture offers a water view of Little Oyster Bay (tidal creek) that can be enjoyed any time of year. This property offers Wi-Fi and is pet friendly! Don't miss out!

- 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.

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 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.

-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. 

Hailey's Round House

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Screened Porch
Internet

Check out Chincoteague’s newest Piney Island vacation rental! Hailey’s Round House is in a prime location on Chincoteague, in a quiet development road but just a short walk to the bridge to Assateague and the Maddox Boulevard shops and restaurants!  You could take a bicycle or short drive to the Assateague beach and access to all of the bicycle trails around Chincoteague and Assateague to enjoy the wild ponies or many of the restaurants on Chincoteague.   

Hailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed.  You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay! 

- 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 312

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pool
Internet

Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are TVs in all the bedrooms, and a computer desk to work from. Villa 312 will sleep 8, and features lots of extras including beach gear and baby gear for your use, as well as a 14' boat slip. Your rental also includes the use of the Sunset Bay pool and fitness area. Located adjacent to our historic downtown area, where you'll find gourmet food shops, boutiques, a public library, galleries and fine dining - all with a short stroll. Come and enjoy a Sunset Bay vacation! | Note: This villa has access to a 14' boat slip.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Heron Landing

2 Bedrooms
1 Baths & 1 Half
6 Guests
Chincoteague Island
Charcoal Grill
Internet

Three words : Charming. Coastal. Cottage. Located just off of Ridge Road, in the center of the island, you'll find this adorable abode. 'Heron Landing' is newly remodeled. Downstairs you'll find an open floor plan with a fully equipped kitchen - with range, refrigerator, and dishwasher. A breakfast bar to enjoy a quick bite before you head to the beach. A comfortable and cozy living area with television. A half bath and washer and dryer can also be found downstairs for your convenience as well. A small porch with sliding door is located off of the living room, allowing you to crack open to let in the island breezes flowing over Assateague Channel. Upstairs you'll find the two bedrooms, both with queen beds. Beautiful, rustic, nautical themed decor. A full bath with tub/shower is also located upstairs as well. Enjoy your cup of coffee or cocktail on the cute patio area outside, or just to get a little extra island sunshine. Memorial Park is an easy walk or bike ride down the street, with a great pier for fishing and crabbing, tennis courts, and walking paths.

- 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.

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 119

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

Immerse yourself in luxury for days at this pristine waterfront villa! This condo unit provides the most spectacular views of the Chincoteague Bay, coupled with some unforgettable sunsets. Sunset Bay Villa 119 offers first floor living throughout with easy access to the condo amenities. Not to mention, convenient walk-out access to the marina boardwalk and boat dock. An open floor plan, including lots of windows that boast those beautiful bay views! Upon entering you will find two bedrooms- One is furnished with two twin bunks, as well as a TV. The 2nd bedroom features a queen size bed and also offers a spectacular waterfront view. There is a shared bathroom with a tub/shower combo in the hall, as well as a washer and dryer in the laundry room. As you make your way further into your beach abode, you will find a large open kitchen featuring granite countertops, BRAND NEW stainless steel appliances, and all the essential cookware to prepare delicious meals during your stay. The primary en-suite is situated so as to fully encompass the most captivating water views, while also offering a luxury bathroom with a tiled shower and jacuzzi tub. Enjoy a relaxing evening beverage while sitting on the balcony watching the sun set, or a nice cup of coffee in the morning. The balcony is accessible from both the primary bedroom suite and the open living area.  Enjoy the convenience of close-by restaurants, shops, movie theater and much more with the proximity of Sunset Bay to the Downtown Chincoteague area. ** NEW FOR 2025: Brand new appliances, new flooring and other upgrades! You won't be disappointed! **

- 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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