Vacation Rental Homes

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

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

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

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

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

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- No pets are permitted on the premises.

- Community amenities require passes for an additional fee.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities.

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

If you're familiar with the island you know that the best sunsets can be found on Main Street, and the sunsets waiting for you at Sunset Dreams (located on south Main Street), are NO EXCEPTION. A luxury waterfront townhome overlooking Chincoteague Bay, offering 3 bedrooms and two and a half baths - with a private pier, it's the perfect place to unwind and get on "island time". On the lower level you'll find the open area kitchen and dining area that features a stunning view of Chincoteague Bay and the salt marsh - that has everything you'll need to enjoy the various fresh catches waiting for you just off of the dock, or at our local seafood markets. A comfortable living area also boasts a beautiful waterfront view, with sliding doors that open up to a lovely little sitting porch - perfect for taking in the sunset with a cocktail without having to go too far. There is also a bedroom downstairs with two twins, a half-bath powder room, and a beautiful large sunroom/sitting area - great for sneaking away for a minute to get some work done or curl up with a good book. On the upper level you'll find the master bedroom with a queen bed, a full bath, and a beautiful waterfront view. Another bedroom with a queen bed is upstairs as well. A full bath can also be found upstairs in the hallway, and both bedrooms have televisions. Full sized washer and dryer for washing all those beach towels and bathing suits. You have full access to the dock across the street, so bring your fishing poles and crabbing gear (or visit Captain Steve's on Maddox Blvd to get what you need!). You're a quick two-minute ride to downtown to restaurants and the grocery, or an easy bike ride to the carnival or the sub shop to grab a quick bite to eat. Come stay with us and enjoy sweet dreams at Sunset Dreams, and bring along your favorite four-legged friend, as this rental is dog- friendly! Need more space? Rent "Saltwater" right next door! Note: The pier is shared with the other 2 adjoining townhomes.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

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

This great contemporary beach home is located at the edge of the community harbor area, a perfect location for you and your guests. As a pet friendly house, you'll enjoy the wide open spaces for your dogs. The home features an open floor plan with a lovely eat-in (and completely renovated!) kitchen and cook area that is flanked by a huge screened porch overlooking the community harbor. You can enjoy all your meals on the porch! In addition, you'll find bright, airy and spacious bedrooms with TVs including a master bedroom suite with King size bed and private bath. There's plenty of parking. You and your guests can crab and fish from the community dock, located just a few steps from your door. Enjoy a great vacation at Osprey!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 3. 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.

Only for the discerning traveler, 'Wildcat Retreat' is the newest in luxury vacation accommodations on Chincoteague Island. The reverse floor plan is over 2,800 square feet and offers views of the bay and marshlands where wildlife abounds from nearly every room. The first floor features 4 bedrooms, all en-suite with full bathrooms and a large recreational room with second kitchen and waterside deck. The second floor features the main living areas - living room, dining room, kitchen, powder room - as well as another waterside deck and screened porch. If you enjoy fishing and crabbing, or just sitting at the water's edge, you'll LOVE the 500' private pier that extends into the Chincoteague Bay! Vacationing with a large group? Check out the sister house 'Wildcat Haven' right next door!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 3. 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.

Nestled in the heart of historic Cape Charles, this meticulously renovated family residence stands as a testament to thoughtful design and artistic vision. Originally conceived as a duplex, this home has been masterfully transformed into a spacious single-family haven, where European sophistication meets coastal charm.

The first floor unfolds with an open-concept design, anchored by a gourmet kitchen that would delight any culinary enthusiast. Equipped with premium appliances and an impressive array of cooking accessories, including three distinct coffee-making options, the space beckons both casual cooks and seasoned chefs. The dining area comfortably seats eight, while a cozy coffee nook and music corner, complete with guitars and microphones, add playful touches to the living space. Through elegant French doors, discover an entertainment room featuring a carefully curated vinyl collection for music aficionados.

Ascending to the second floor, two identical queen bedrooms offer serene retreats, while the California king guest room provides a luxurious escape with its distinguished wingback chair and footstool arrangement. A dedicated study space ensures connectivity with fiber optic internet, perfect for remote work or planning your next coastal adventure. The crown jewel of the upper level is the remarkably spacious family bathroom, spanning 250 square feet of pure indulgence.

The outdoor space embraces coastal living with a welcoming front porch, expansive deck, and thoughtful amenities including a fire pit, and grill area. The corner lot location provides ample street parking, accommodating boats and extra vehicles with ease.

This home's proximity to Cape Charles' treasured attractions enhances its appeal, with the historic district and beautiful beachfront just moments away. A decade of careful curation by its overseas owners has infused this residence with a distinctive London-inspired aesthetic, creating an unexpected and delightful fusion of sophisticated urban style and relaxed coastal living.

Special Notes:

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. All pets must be disclosed prior to arrival.

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