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Trembling Bay

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet

This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. Come and see for yourself; you won't be disappointed!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pet Friendly with a fee, No cats, 2 dogs max. ($150 per pet) 

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

An Unfettered View

2 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Internet
Outdoor Shower

This beautiful 2 bedroom ranch home has a quiet, out-of-the-way location situated on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck. It's perfect for crabbing, kayaking & canoeing! An Unfettered View features all amenities including a private master suite with full bath, central air, all appliances including dishwasher, washer/dryer, wireless internet service and a wonderful family room on the waterside of the home. Tastefully furnished and very accommodating, this is a great vacation spot! An Unfettered View is wheelchair accessible.

- 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.

Diving Duck

5 Bedrooms
2 Baths & 1 Half
10 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Hot Tub
Internet
Outdoor Shower

If you're looking for the complete vacation package, look no further! This 5 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room with access to the waterside deck, a large dining area, kitchen with all the counter space you'd ever need, a half bathroom, and the master bedroom with private bath (with custom tile shower and soaking tub). Upstairs features a landing area with sofa and foosball table, 4 more bedrooms and another full bathroom. Aptly named, 'Diving Duck' is the perfect spot for watching the ducks and wildlife pitch in the bay just out the back door. There's even a floating dock perfect for launching canoes and kayaks! And as if all of that is not enough, the Captains Cove community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. (Fee applies for usage of community amenities.) This rental home is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions). What more could you ask for? Book your stay at 'Diving Duck' today! Additional game room with wet bar and pool table, and a private hot tub. All of this in addition to interior updates and renovations!

- 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. Although the rental home can accommodate up to 10 guests, only 8 guests are permitted to use the community amenities (pool, etc.) at a time.

- 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. 

 

Sunkissed Shores

4 Bedrooms
4 Baths
15 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Sunkissed Shores invites you to experience waterfront living at its finest. This expansive four‑bedroom, four‑and‑a‑half‑bathroom retreat sits directly on Chincoteague Bay, offering sweeping water views and unforgettable sunsets from every room. Each bedroom features its own private balcony and ensuite bath, including two king suites on separate levels for added privacy. A cheerful bunkroom provides flexible sleeping for families and groups, and thoughtful touches like two pack ’n plays and a highchair make traveling with little ones effortless.

The heart of the home is the stunning great room, where soaring ceilings and dramatic walls of windows bring the bay right inside. During cooler months, the seasonal fireplace transforms this space into a warm, inviting haven—perfect for watching winter sunsets or enjoying a quiet evening indoors. A fully equipped  kitchen—with generous counter space, quality cookware, and every gadget you could need—makes meal preparation and entertaining a pleasure. Just off the living area, an enclosed all‑weather gazebo opens to a large waterside deck, creating the perfect setting for crab feasts, morning coffee, or simply relaxing as the sky shifts from gold to pink each evening.

Upstairs, the game loft offers entertainment for all ages with a classic 1980s Space Invaders arcade machine, a commercial‑grade 4‑player arcade table with over 2,500 games, a 77" TV, board games, a chess/checkers table, and a giant wall‑mounted Connect 4. A queen sleeper sofa provides additional space for guests, and each upstairs bedroom sits in its own private wing for a peaceful retreat.

Step outside to your private pier, where you can fish, crab, or launch kayaks directly into the bay. The bulkheaded shoreline offers easy access to the water, and the eastern side of the property provides serene sunrise views over the marsh—giving you the rare opportunity to enjoy both sunrise and sunset from the same home. With unmatched views, thoughtful amenities, and room for everyone to unwind, Sunkissed Shores stands apart as a place where memories are made and every day ends with a sunset worth savoring.

- 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.

Stingray

2 Bedrooms
2 Baths
4 Guests
Chincoteague Island
Waterfront
Internet

Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, features all amenities, as well as master bedroom suite with king bed & waterside balcony. Many extras like a flat screen TV and a Lazy Boy leather recliner. The open floor plan is great and features a breakfast bar between the kitchen & dining area!

- 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.

Sunrise View

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
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 WATERFRONT 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. View the water from almost anywhere…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, where every room has a view!  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 — day after day.

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. Quietly listen to music and watch the Purple Martins swirl about … just off the porch. It's the kind of space where conversations linger and worries disappear. It's magical.

Boaters delight in the fact that they can tie-up their boat right at the home. Using the community boat ramp makes this easy. Boat, kayak or fish right from the property.

Beyond the home, adventure awaits. Explore the nearby Island Nature Trails 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.

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.

 

Creek House

5 Bedrooms
4 Baths
14 Guests
Mainland
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

Creek House, Privately located in an imaginative setting; nature and history are perfectly coupled with luxurious accommodations.

Rounding the corner of the private country lane, you'll sense something special unfolding before you. What can best be described as an imaginative setting, nature and beauty are perfectly coupled with luxury - a modern 5 bedroom home that's part of a family compound is before you. It sits at the edge of Holdens Creek, where the Pocomoke Sound meets the Chesapeake Bay. You’ve reached Creek House!  Newly renovated and nothing short of spectacular, the WOW factor kicks in as soon as you enter.  Large living spaces with breathtakingly scenic and panoramic water views captivate you. There are Waterside balconies on every level and world class amenities at every turn.  Professional interior finishes bring true elegance to the home’s aesthetic of simple, sexy... and just plain cool. The natural flow from space to space is perfect for a couple to enjoy a romantic getaway or for a large group gathering.  With room for 14 guests, the generous bedrooms offer waterside balconies and marble bathrooms. The kitchen/ dining area can host any size party.

In the garage level of the home, enjoy a game of ping pong on the regulation size table or play a game of cards with the family! Also enjoy the shared use of 2 single kayaks, 1 canoe, and 1 paddleboard.

'Creek House' has partnered with our friends at Sun Outdoors Resort (located less than 2 miles from the house) so that all guests may enjoy the fun resort amenities FREE OF CHARGE. This extra bonus includes a private beach w/ water rentals, pool, playground, "snak shak", comfort stations & more! 

Where is Creek House located? Only a 20 minute drive to Chincoteague Island, Creek House is situated on one of the most beautiful slices of Virginia's Eastern Shore. Day trips to the beach are easy and convenient. Other beach towns like Ocean City, MD and Cape Charles, VA are less than an hour away.  

Creek House has a boat launch, two docks, five porches and a 20’ radius fire pit with outdoor lighting and wi-fi (Bluetooth) speakers system. Simply staying on the property to enjoy a vacation with down time is an option with endless possibilities. The entire compound is available for events and can accommodate up to 18 people (each of the three dwellings are rented separately). Pets will be considered upon request. 

In addition to The Creek House, the compound is also home to two luxurious cottages: Porter’s Barn and Hosta Cottage. Please note that this listing is for Creek House only; the other two cottages - Hosta Cottage and Porter's Barn - must be booked separately. A direct inquiry should be sent for special event pricing or if you wish to rent the entire compound.

GPS is inconsistent on Holden’s Creek Road. Please follow Holden’s Creek Road approximately 1/2 mile and take the first right Drive down the private gravel driveway (labeled: Porterville RD)  past the horse pasture. Take a left at the Y and follow the driveway to the property.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- This property is pet friendly on a case by case basis, with a pet fee per pet. Pet fee is $200 per pet. All pets must be disclosed prior to arrival.

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

Sunrise Shore

3 Bedrooms
3 Baths & 1 Half
14 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Pool
Hot Tub
Internet

Spend your precious vacation time at this truly stunning, one-of-a-kind architectural masterpiece! From the moment you walk in the French entry doors, you'll be "wowed" by the floor to ceiling windows and 3-sided glass fireplace. The chef's quality kitchen is brand new with stainless steel appliances and granite counter tops. There are multiple decks for enjoying some relaxing downtime and taking in the unobstructed views of Oyster Bay. Professionally decorated with clean, modern Bohemian-chic decor and furnishings, you'll find yourself surrounded by simple, upscale comfort. There's a 70" TV in the living room, and all the bedrooms feature their own flat-screen TVs and Amazon Echo devices. Stream all of your favorite shows from Hulu, Netflix or Disney+! "Sunrise Shore" is located in one of Chincoteague Island's most popular waterfront residential communities - Oyster Bay I. Conveniently located to Maddox Blvd. (Beach Road) and downtown Chincoteague, yet far enough to escape the hustle & bustle. | | The main level of this home features the main living areas (kitchen, dining room, living room), a powder room, a pool shower bathroom ,and the master bathroom en suite. The upstairs features 2 more bedrooms, both with private balconies, and a full bathroom. There's also an additional loft sleeping area. | | The outdoor areas offer exceptional entertaining and relaxation space. Cool off in the 10' x 40' saltwater in-ground pool, or gaze at the stars as you spend the evening in the 6-person hot tub. Dine al fresco on one of the many decks, all while enjoying the water views. There's plenty of room in the yard for a game of corn hole or catch.

- 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.

Castlebar

5 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Luxury waterfront home in Salt Marsh Landing - an upscale residential community on the northern tip of Chincoteague Island. Spectacular sunsets! A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Tastefully appointed and architecturally pleasing, Castlebar features a main level great room flanked by wall of beautiful custom windows and high cathedral ceilings. The views of Chincoteague Bay are priceless. The open kitchen area features ample counter space for meal prep, and the large harvest dining table is perfect for gathering the whole group for a meal. There are hardwood floors, and a two-sided fireplace that is shared with the adjoining cozy den. The first floor also features a full bath and large bedroom that looks out on the bay. The second floor hosts the primary bedroom suite, containing a private bath with separate shower and whirlpool tub. A sliding French door leads out to a balcony providing more views of the bay to enjoy. Two additional bedrooms and full bath complete this floor. Amenities also include a private, full sized outdoor shower, wireless internet service, additional under-counter ice maker & more. Castlebar is available 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.

Day Dream Believer

4 Bedrooms
4 Baths
10 Guests
Cape Charles
Waterfront
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

Welcome to 'Day Dream Believer' on Virginia's coastline in Cape Charles, VA. This remarkable house is now available for rent, offering a fantastic opportunity to experience luxurious coastal living. With 4 bedrooms, 4 bathrooms, and ample parking for 4 vehicles, this new construction home caters to luxury, comfort and convenience!  This beautiful home is located in the coveted resort community of Bay Creek and is awaiting your ideal vacation experience.

As you step inside, you'll be greeted by the exquisite craftsmanship and attention to detail that defines this property. The stunning quartz countertops add a touch of elegance to the spacious kitchen, which will aspire the chef within you. Boasting a  48” Wolf stove/oven with 4 burners and a 24” griddlehard surface countertops, a breakfast nook and uncompromised views; this room is open to the spacious living area with high ceilings and abundant natural light. Whether you're hosting a feast or enjoying a quiet meal with family, this kitchen is sure to impress. Spread across three levels, the home offers plenty of room for everyone to find their own space. Take in the grandeur of the vaulted ceilings while cozying up next to the inviting gas fireplace on chilly evenings. With two primary bedroom en suites, this property caters to those seeking privacy and luxury. Each bedroom is designed with your comfort in mind, providing a serene retreat after a long day. Enjoy the convenience of having your own private bathroom where you can unwind in style. In fact, on the 3rd floor you are greeted with the spacious owner's suite, complete with a private sitting area that is perfect for reading, watching your favorite show, or enjoying a cup of coffee. 

On the lower level, you have the convenience of a two car garage for loading and unloading - complete with another bedroom, full bathroom, and featuring a tub/shower combo. Restore and relax out back, while taking in the beautiful water views or make your way into town where you will find all the charming town of Cape Charles has to offer. This remarkable vacation spot will leave you with only one regret - that you didn't book a longer stay!

But that's not all – residing in this house means gaining access to the resort amenities at Bay Creek Resort. Dive into a world of relaxation and entertainment as you indulge in community offerings such as golf courses, swimming pools, dining options, nature preserve and more. Discover a lifestyle that blends tranquility with fun-filled activities right at your fingertips.

Located in beautiful Cape Charles, VA, this house positions you just moments away from pristine beaches and charming downtown shops and restaurants. Embrace the coastal lifestyle as you soak up the sun on sandy shores or embark on boating adventures along the Chesapeake Bay. Don't miss out on this incredible rental opportunity at Day Dream Believer! Experience the epitome of beach and resort living with its modern features, community amenities, and prime location. 

BED CONFIGURATION: Primary Bedroom 1: King & Queen Sleeper Sofa (in separate sitting area) // Primary Bedroom 2: Queen bed // Bedroom 3: Queen bed // Bedroom 4: Queen Sleeper Sofa

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, 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.

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