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Virginia Lee

2 Bedrooms
1 Baths & 1 Half
4 Guests
Cape Charles
Internet

Experience vacation living at its finest in this modern two-bedroom, one-and-a-half-bathroom condominium nestled in the heart of Cape Charles. This thoughtfully designed retreat features an open floor plan complemented by a full kitchen with brand-new appliances for the culinary enthusiast.

The inviting living room showcases eye-catching skylights that flood the space with natural light, while a large television and cozy fireplace create the perfect atmosphere for relaxation. The comfortable primary bedroom offers a king bed and connects to a custom-tiled bathroom, while the upstairs bedroom includes an adjoining powder room for added convenience.

What truly distinguishes this property is its spectacular rooftop terrace, complete with a wet bar sheltered by an elegant pergola — ideal for entertaining guests or enjoying breathtaking sunset views over the Chesapeake Bay.

The condo offers unparalleled convenience, situated just blocks from Cape Charles' pristine beachfront and within easy walking distance to the town's vibrant center. Imagine strolling to local restaurants, browsing unique boutique shops and art galleries, or finishing the day with a hand-crafted cocktail or libation at one of the towns favorite night spots — all without needing to use your car.

Whether seeking a peaceful weekend getaway or an extended coastal retreat, this charming condominium offers the perfect blend of modern comfort and small-town bayside living.

PLEASE NOTE: 'Virginia Lee' is one of 5 luxury apartments offered within the 'Cape Dunes' complex. This being the case, some amenities and spaces are shared. This includes the washer & dryer, ice maker and roof top terrace. Parking is on-street and not reserved. 

- No smoking is permitted. 

- 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.

 

Sunset Bay Villa 118

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Waterfront
Boat Dock
Pool
Internet

Come and sit a spell. Grab a cocktail and watch your worries sail away as you enjoy the cozy private outdoor seating area to be found at Sunset Bay Villa 118. The unit is on the ground level, providing easy access after a long day at the beach. Beautifully styled with nautical decor and special attention to detail. Situated on the edge of the bay, this villa offers a private balcony with walk-out access to the marina and a reserved 40' foot deep-water boat slip. Villa 118 at Sunset Bay boasts an en-suite bedroom with king bed, private bath featuring a stand up shower AND a bathtub - along with private outdoor patio access from the bedroom. Two other bedrooms feature a king in one, and a twin in the other. Fully equipped kitchen and dining area with coffee maker, refrigerator/freezer, dishwasher, electric range, and plenty of countertop for that family seafood feast you will want to make while you're with us. Have a few friends sit at the bar while you mix up a few cocktails, then enjoy "people-watching" on the Chincoteague Channel as the evening picks up. Once the sun goes down you can retire to the cozy living area in the heart of the villa. Maybe a movie on the flat screen? Or perhaps a game of chess? No matter what you decide on, you and your guest will most certainly enjoy your stay at Sunset Bay Villa 118. | Please Note: This unit includes a deep-water boat slip and use of the marina.

- 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.

Blue Crab Bungalow

1 Bedroom
1 Bath
5 Guests
Chincoteague Island
Pet Friendly
Internet
Outdoor Shower

Welcome to this charming bungalow located in the center of Chincoteague Island! This delightful house offers a cozy and comfortable living space, making it the perfect place to call home. With 1 bedroom and 1 bathroom, this property is ideal for individuals or a small family looking for a serene retreat. As you step inside, the throw-back retro kitchen adds character to the home and makes cooking an enjoyable experience. Whip up your favorite meals while reminiscing about the good old days. The kitchen is equipped with all the necessary appliances to satisfy your culinary desires. You'll be greeted by the warmth of the main bedroom featuring a comfortable queen bed. The second sleep area serves as both a sleeping and an office space, with a twin pull-out sofa providing versatile accommodation options. Whether you work remotely or simply need a quiet space to focus, this flexible layout has got you covered! The bungalow is close to town and 'Beach Road' - convenience is at your fingertips. Enjoy easy access to local amenities such as shops, restaurants, and entertainment options. Whether you're in the mood for a leisurely stroll or need to run some errands, everything is just a short distance away. After a long day, relax and unwind in the enclosed front porch. This inviting space is perfect for enjoying your morning coffee or savoring a glass of wine in the evening breeze. Additionally, there's an outside shower, allowing you to rinse off after spending time at the nearby beach. With parking spaces for 2 vehicles, parking won't be a hassle. Don't miss out on the opportunity to make this charming bungalow your next vacation spot! With its convenient location, versatile layout, and retro charm, it's sure to steal your heart. 

- 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 number of pets allowed: 2. Pet Restriction: small dogs 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.

Channel Winds

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

Welcome to your dream island getaway on Chincoteague Island! This waterfront townhouse sits right on the Assateague Channel, serving up jaw-dropping views of the lighthouse that'll make your morning coffee taste even better.

With three bedrooms and two and a half bathrooms, there's plenty of room for the whole crew. The primary en suite bedroom is the real showstopper here, featuring a private balcony that overlooks the water. Imagine waking up, stepping outside, and watching the sun paint the channel gold. Not a bad way to start the day, right?

The outdoor living space is where the magic really happens. Two levels of waterside decks give you plenty of room to spread out, soak up the views, and just breathe. Fire up the gas grill for a seafood cookout while the kids explore, or simply kick back and watch the boats drift by. Life moves a little slower here, and that's exactly the point.

Adventure seekers, this one's for you. Kayaks, a paddle board, and bicycles are all provided, so you can hit the water or cruise the island without packing extra gear. The famous Assateague Wildlife Refuge and its stunning beach are just a short trip away, perfect for spotting wild ponies and catching some waves.

Right around the corner, you'll find Veteran's Memorial Park with a playground, tennis courts, basketball, and more to keep everyone entertained. Need groceries? Island Foods is a quick ride up the road. And for some splashy fun, Maui Jack's Waterpark is nearby too.

This is island living at its finest. Don't let this one slip away, book your island vacation 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.

Southern Dream

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water View
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Charming 3 bedroom ranch home located in one of Chincoteague Island's residential communities. Nice, quiet location with a water view of Oyster Bay. You'll enjoy the easy, one-story floor plan with open living room/kitchen/dining areas. If you love the outdoors, spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high speed internet, charcoal grill and an outside shower will ensure your comfort during your 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.

Beach Bettie's

3 Bedrooms
1 Bath
6 Guests
Smith Beach
Waterfront
Internet
Outdoor Shower

Discover coastal living at its finest in this enchanting three-bedroom cottage nestled along the pristine shores of the Chesapeake Bay. This waterfront retreat offers an unparalleled opportunity to experience the serene beauty of Virginia's Eastern Shore while enjoying the perfect blend of comfort and bayside charm.

The thoughtfully designed interior features three inviting bedrooms and a full bathroom, creating an ideal space for multi-seasonal getaways. Water-facing windows throughout the home frame spectacular views of the bay while allowing natural light to cascade through the living spaces, creating an atmosphere of warmth and tranquility.

Step outside onto your private slice of paradise, where meticulously maintained landscaping creates a picturesque setting for outdoor entertainment and relaxation. Multiple seating areas have been strategically placed to maximize the breathtaking vistas, making it the perfect spot to unwind while watching the sun paint the sky in brilliant hues during the legendary Chesapeake Bay sunsets.

This exceptional property's location offers the best of both worlds – peaceful seclusion with convenient proximity to beloved local attractions. Just minutes away, you'll find the renowned Cape Charles Beach, where soft sands and gentle waves await. The historic downtown district, with its charming boutiques, restaurants, and galleries, is also within easy reach. Nature enthusiasts will appreciate being near the Savage Neck Dunes State Natural Area Preserve, offering pristine hiking trails and unspoiled coastal wilderness.

Whether you're seeking a peaceful year-round residence or a memorable vacation retreat, this bayside haven provides an extraordinary opportunity to embrace the coveted coastal lifestyle. The combination of waterfront splendor, thoughtful design, and prime location creates an unmatched living experience on Virginia's celebrated Eastern Shore.

Special Note: The loft room is accessible by a ladder and, because of such, is not an advertised sleeping area. There is a Full-size bed in the loft, however, no linens are provided for this bed. 

- 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.

The Pines on Finney Creek

3 Bedrooms
3 Baths
12 Guests
Waterfront
Boat Dock
Gas Grill
Internet
Outdoor Shower

Wake up to birdsong, spend the afternoon paddling around, and wrap up the evening watching the sky light up over Finney Creek. Sounds pretty good, right? This freshly renovated three-bedroom, three-bathroom home makes that whole relaxing routine your new normal.

Sitting on private acreage in a quiet, tree-lined pocket of the Town of Onancock, this rental is made for folks who take their downtime seriously. You've got your own pier and boat dock reaching right into the creek, so kayaking, fishing, or just dipping your toes in the water is always an option. The sprawling decks and big outdoor area leave plenty of room to grill, hang out with friends, or plant yourself in a lounge chair and stay put for a while.

When the weather isn't cooperating, head into the roomy sunroom. There's a pool table and other activities ready for a little friendly competition. Inside, the upscale kitchen actually makes cooking fun, and the newly remodeled bathrooms have that clean, just-finished feel you'll notice the second you walk in.

Honestly though, the setting steals the show. Wildlife roams around like it owns the place, the pace stays nice and slow, and the quiet here is the kind you didn't realize you'd been missing. Even so, charming downtown Onancock is only a few minutes off. East Point Marina and the Onancock Wharf are close by for some easy waterfront wandering, Food Lion handles the grocery runs, and Chincoteague Island makes for a fun day trip whenever you feel like venturing out.

So if you're ready to swap the everyday noise for the gentle sound of the creek, this place is waiting. Give us a call and schedule your stay today. You'll be glad you did.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This home is pet friendly with an additional 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.

Serenity at Deep Hole Hideaway

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

Welcome to your blissful oasis, "Serenity at Deep Hole Hideaway!" This charming haven has been given a complete makeover to cater to all your vacation dreams. The kitchen is stacked with top-notch gadgets to whip up that perfect meal. The living room features a cozy sleeper sofa to squeeze in a few extra guests. The main bedroom boasts a luxurious queen-sized bed, while the guest room offers a snug twin daybed, providing ample space for up to six guests. Step outside and relax on the deck, indulging in a long-awaited book. And, if you're in the mood for some classic campfire fun, gather around the firepit and toast up some scrumptious S'mores and hotdogs!

- 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.

My Island Escape

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Water Access
Boat Dock
Charcoal Grill
Internet
Outdoor Shower

Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely immaculate! Luxury finishings, tastefully appointed furniture and decor make for a flawless backdrop to your next vacation. The living room at My Island Escape features ample comfortable seating and a flat screen television, and flows into the fully equipped, gourmet, eat-in kitchen that features a large island and plenty of space for cooking, dining, and enjoying meals with the family. The master bedroom features a Queen size bed with an en suite highlighted by a large soaking tub, double vanity, and separate glass stand up shower. The two other bedrooms in the home are close by a full bathroom located off the hallway. Another bonus in this home is the spacious laundry room complete with a full-size washer and dryer, iron and an ironing board, and connects to a convenient half bath. Outside, you will find deck space with outdoor furniture, and a picnic table with umbrella for outdoor dining. If you are looking for a clean, relaxing, upscale rental with great attention to detail ? look no further and escape to My Island Escape!

- 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.

Blue Pointe Bayside

3 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Waterfront
Gas Grill
Screened Porch
Internet
Outdoor Shower

Spectacular waterfront home on the end of a cul-de-sac! Bright, airy and immaculate! Four decks, including one off of the stunning 2nd floor Private Master Suite. Dramatic cathedral ceiling in the cozy, waterfront living room. A screened porch to host an outdoor dinner. Central heat for those off-season stays, and Central A/C for the summer stays, make this the perfect vacation house all year 'round. A sunny, well equipped, eat in kitchen for the gourmet cook. Down-draft cook top and gas grill; perfect for any meal. Beautiful sunsets on the Chincoteague Bay - Water views from every room! Large, hot water outside shower and an oyster shell path to the water so you can easily walk out to the bay to crab, fish and kayak.

- 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.

Beachin' at the Cove

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Pool

Come and enjoy a private place to call home during your much needed vacation! Beachin' at the Cove has everything you need to enjoy a quick or extended getaway.  The location of this inviting home is superb! Overlooking one of the Shore's best golf courses, Beachin' at the Cove provides a desired location for your perfect beach escape. In this cozy, single family home, you will be greeted by a covered porch where you can sit and sip your morning coffee or tea. You will then enter an inviting, open living area adjacent to the kitchen with access to the large and open back deck. This home offers first floor sleeping quarters as well as a full bathroom and hardwood flooring throughout. Upstairs you will find 2 more bedrooms and another full bath. The beautiful community of Captain's Cove offers many amenities, with something suited for the entire family. Beachin' at the Cove is located just a short distance from waterfront dining on the Chincoteague Bay, 3 pools, a 9 hole golf course, tennis, basketball, fitness, and much more! Conveniently located, you're approximately 20 minutes from Chincoteague Island, 30 minutes from Snow Hill and less than an hour to Ocean City MD.

- 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.

- 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.

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