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Serendipity

3 Bedrooms
1 Baths & 1 Half
6 Guests
Chincoteague Island
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also offers a first floor bedroom (Queen) and half bath.

- 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.

The Great Escape

5 Bedrooms
3 Baths
11 Guests
Cape Charles
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover the charm of Cape Charles in this beautifully restored 5-bedroom, 3-bathroom house, available for your next vacation adventure. Nestled in the heart of downtown, "The Great Escape" places you just minutes away from a vibrant selection of shopping, dining, and entertainment options, including local ice cream shops and mini-golf. Whether you're enjoying the bustling town scene or relaxing at home, this property offers both convenience and comfort.

Step onto the inviting open front porch where you can sip your morning coffee while soaking in the town views. Alternatively, the screened porch provides a tranquil retreat to unwind in the evenings without the pesky insects. Inside, you’ll find a clean and comfortable interior with ample living space that caters to both large and small families alike.

"The Great Escape" is ideal for those seeking a blend of small-town charm and modern amenities, all within walking distance of Cape Charles' delightful attractions. Whether you're settling down with your family or looking for a scenic change of pace, this vacation home promises a lifestyle of ease and excitement. Don’t miss out on making this house your new home away from home — book your getaway today!

- 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.

 

Saltwater

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Welcome to ‘Saltwater', formerly known as 'Logan's Sunset.' A lovely 2 story waterfront townhouse on Chincoteague Bay with gorgeous views from both floors. Experience beautiful sunsets and NASA rocket launches from the front balcony. The screened back porch offers a great source of private outdoor entertainment as it boasts a comfortable six-person dining area. All three bedrooms have their own flat screen tv with cable. The main bedroom includes a desk perfect for working from home, virtual learning and streaming. Saltwater includes high-speed internet and free Wi-Fi. The main bedroom has it's own ensuite full bath with jetted tub/shower. The additional bedroom has a private full tub/shower. The 3rd bedroom has a bunk with two full size beds with an additional twin bed.  Guests can also enjoy the coastal outdoor shower. The private expansive 600 foot shared deep water dock provides hours of endless Saltwater fun! 

Need more space? Rent "Sunset Dreams" right next door! 

Saltwater has a fully stocked kitchen including an outdoor charcoal grill.

- 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.

Star of the Sea

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

Introducing a charming, newly renovated house, offering a perfect blend of comfort and convenience. This single-family home features an inviting sunroom, a brand-new kitchen, four well-appointed bedrooms, including a serene primary bedroom, and two modern bathrooms, all professionally decorated with a delightful beach theme.

Designed to accommodate up to eight guests, the house boasts spacious rooms that ensure ample space for relaxation and entertainment. The living areas flow beautifully outdoors to a superb deck, ideal for enjoying your morning coffee or sunset dinners, surrounded by a spacious yard.

Nestled in a vibrant neighborhood, the property promises a vacation of ease and accessibility. It’s centrally located near the heart of the town, close to a pristine beach, restaurants, and family-friendly activities, including mini-golf and Maui Jack's Waterpark. Nature enthusiasts will appreciate the proximity to the Assateague Island National Seashore, a spectacular location for wildlife and scenic views, while the nearby Downtown Chincoteague Waterfront Park provides excellent opportunities for leisurely activities.

Experience the joy of living where every day feels like a vacation. This retreat is not just a place to stay, but a home away from home. Come and see for yourself!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Home is pet friendly with additional pet fee. 

- 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 Sea Star

3 Bedrooms
2 Baths & 1 Half
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet

Welcome to Blue Sea Star! You'll fall in love with this fabulous 3 bedroom home from the moment you walk in the door. Bright open spaces, lots of windows, wood floors, first floor master bedroom/bathroom, and too much more to name! Located on a quiet cul-de-sac in the popular Oyster Bay II Community just off of North Main Street. Conveniently located just a few minutes from the downtown waterfront park, shopping, restaurants, movie theater and more! Blue Sea Star features a screened back porch, open side and front porches - perfect for relaxing with a cup of coffee in the morning, or cool drinks after a day at the beach, and a great backyard. As a pet friendly rental, you can even bring your four-legged family member!

- 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.

Cockleshell Cottage

3 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage! This modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs features 2 more bedrooms (Double and Double/pull-out Twin trundle), and a full bathroom. Cockleshell Cottage is handicap accessible. Relax and enjoy the breeze on the open front porch or back screened porch. Call us today; this home books fast!

- 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. Pet restriction: limited to two small dogs 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.

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.

Cozy Nest

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water View
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Welcome to "Cozy Nest," a charming home available for your next vacation experience, offering an idyllic retreat with stunning water views! This inviting property spanning over 900 sq. feet can accommodate up to 6 guests, making it an ideal choice for families, friends, or anyone looking to immerse themselves in comfort and tranquility.

 

"Cozy Nest" features two well-appointed bedrooms and two full bathrooms, ensuring privacy and convenience. The primary suite bedroom, encompassing the entire second floor, offers a peaceful haven for relaxation with its serene views, private bath, and private deck access. The first floor provides flexible sleeping arrangements with two twin beds in the bedroom, and a sleeper sofa in the living room. The full bath on the first floor rounds out the convenient layout.

 

The heart of this home is its beautiful outdoor spaces. A screened porch provides a bug-free zone to enjoy the fresh air and scenic surroundings, while the open deck invites you to bask in the sun, stargaze at night, or dine al fresco against the backdrop of picturesque water views. These outdoor areas are perfect for entertaining or simply unwinding after a day's adventures.

 

Pet lovers will be delighted to know that "Cozy Nest" is pet-friendly, and welcomes your furry friends to join in on the family fun. Additionally, with three parking spaces available, guests will find ample parking for their vehicles.

 

Located in a serene setting with captivating water views, this property offers the perfect blend of relaxation and convenience. Whether you're seeking a peaceful getaway or a comfortable base from which to explore the area, "Cozy Nest" promises a memorable stay for all who visit.

- 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.

Gone Coastal

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet

Enjoy the cool breezes coming off the Chincoteague Channel while relaxing on the porch at Gone Coastal! Nestled in a grove of pines and tucked just off East Side Drive, this charming unit has everything your family desires for a wonderful stay on Chincoteague Island. Bright and cheery nautical decor will help to put you on "island time". Featuring two bedrooms, two and a half baths, a spacious living and dining area, and a fully-equipped kitchen. The two bedrooms are on the upper level. The master features a full bed with flat screen television, full bath, and balcony with sliding door and comfortable outdoor furnishings. An additional bedroom featuring a full size bed and double bunk, and a full bath is located in the hallway upstairs as well. On the ground floor you'll find a spacious living area with large flat screen tv, plush seating, and plenty of reading material. The eat-in kitchen features everything you'll need to prepare and enjoy meals "at home" - electric range, roomy refrigerator, dishwasher, coffee bar, and dining table. A full-sized washer and dryer are located in a utility closet just off the kitchen, and a barbecue grill is located on the back porch for your convenience. Located centrally on the island - you're a quick bike ride or easy walking distance to the commerce on Maddox Boulevard or downtown Main Street, or to Memorial Park located just down Eastside Drive. Pop into one the oyster farms and grab a sack to bring back and enjoy with a glass of wine as the sun sets on another day Gone Coastal. Please Note: No boats or trailers are allowed at the complex.

- 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.

Windshadow

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining area. Walk through the French doors off the living room to a large screened porch and sky deck overlooking the Chincoteague Bay. There is a first floor King bedroom with en-suite bath and two twin bedrooms on the second level. Windshadow is a premier PET FRIENDLY vacation rental.

- 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.

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.

Play by the Bay

3 Bedrooms
2 Baths & 1 Half
6 Guests
Cape Charles
Town & Country
Internet
Outdoor Shower

New to the rental market, "Play By The Bay" is a brand-new 3-bedroom, 2.5-bath house designed for easy coastal living in Cape Charles—where your biggest daily decision is beach time or backyard time.

Step inside to fresh finishes and a bright, open layout that keeps everyone connected, from morning pancake duty to game night. The upgraded chef’s kitchen is the star of the show, with plenty of workspace for slicing, sautéing, and showing off your “I totally meant to do that” plating skills. The main living area flows naturally for lounging, streaming, and post-sunshine naps.

The primary en suite offers a calm retreat, while two additional bedrooms provide flexible space for guests, kids, or that quiet workspace that you may need on occasion. With two full baths plus a convenient half bath, morning routines stay conveniently civilized.

Outside, enjoy a large yard set up for fun—bring your competitive spirit for lawn games or simply claim a chair and supervise like a professional. Bicycles are included, because Cape Charles is better at a relaxed pace and parking worries are not invited.

You’re close to historic downtown Cape Charles for shops, dining, and strolling, and the beachfront is an easy ride away when the water starts calling your name. Groceries are nearby too, so ice cream runs can remain an important part of your schedule.

Ready to make this coastal getaway your 'home away from home'? Book today and start your annual vacation tradition!

- 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.

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