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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 property is pet friendly. An additional fee of $200 per pet will apply. Pet restriction: NO CATS. Max 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.

Bay Haven

3 Bedrooms
2 Baths & 1 Half
6 Guests
Captain's Cove
Waterfront
Boat Dock
Pool
Internet

Ever dreamed of a home where water views greet you from literally every room? This contemporary three-bedroom, two-and-a-half-bathroom house turns that daydream into your everyday reality, blending sleek modern design with the kind of relaxed waterfront rhythm that's tough to beat.

Walk through the door and the open floor plan immediately shows off, letting light and shimmering water views flow freely from one space to the next. Whether you're whipping up dinner, sprawling on the couch, or catching up with family, the sparkle of the water stays in view the entire time. It's the sort of layout that makes hosting feel effortless and lazy days feel downright luxurious.

Three comfortable bedrooms give everyone space to spread out, with the primary bedroom carving out a peaceful spot to recharge. The contemporary finishes lend a crisp, current feel throughout, so the whole place reads clean and bright.

Then there's the neighborhood, and Captain's Cove genuinely delivers. Think swimming pools, a fitness center, a playground for the little ones, golf for the swing enthusiasts, an on-site restaurant, and a marina for boat lovers. It's practically a vacation resort you get to call home away from home.

When wanderlust strikes, adventure sits close by. Maui Jack's Waterpark brings splashy thrills, the legendary Assateague Beach offers wild ponies and endless beach shoreline, and the boardwalk buzz of Ocean City is an easy day trip away.

Ready to live where the water never leaves your sight? Book your vacation today.

- 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. 

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.

- 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.

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. An additional fee of $150 per pet will apply. Maximum pets allowed: 2. Pet Restriction: 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.

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.

Heron's Hideaway

3 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover your perfect family retreat at this charming three-bedroom, two-bathroom house nestled in peaceful Oyster Bay II on Chincoteague Island. 'Heron's Hideaway' welcomes up to 12 guests, making it ideal for multi-generational gatherings, friend reunions, or anyone seeking a memorable coastal escape.

The heart of this home lies in its thoughtfully designed layout, offering both communal spaces for togetherness and quiet nooks for those precious moments of solitude. Fall in love with the screened-in porch—your new favorite spot for morning coffee, afternoon board games, or listening to gentle summer rain. When you're ready for fresh air and broader views, head upstairs to the deck where peaceful vistas and cooling breezes create the perfect setting for birdwatching or evening stargazing.

The well-appointed kitchen makes meal preparation a pleasure with its dual-oven electric stove, elegant granite countertops, and full-size appliances. Families will appreciate thoughtful touches like the provided high chair, pack-n-play, and collection of board games suitable for all ages.

Located in a tranquil residential neighborhood, this trusted vacation favorite sits at the end of a quiet cul-de-sac, surrounded by lush trees and natural landscaping that creates a beautifully secluded atmosphere. You'll feel worlds away from everyday stress while remaining just a short drive from Assateague Wildlife Refuge, pristine beaches, local restaurants, and charming shops. Remote workers will appreciate the private business nook complete with desk and monitor, allowing you to balance productivity with relaxation. Since 2018, this beloved hideaway has hosted everything from girls' weekends and holiday celebrations, to hunting expeditions and peaceful solo retreats.

Whether you're seeking adventure at nearby Maui Jack's Waterpark, exploring Waterfront Park, or simply enjoying the serenity of island life, this exceptional rental offers the perfect base for your Chincoteague "home away from home" experience.

- 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: 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.

Marsh Point

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Located just off of Ridge Road on the southern portion of the island, you'll find Marsh Point. A two bedroom, two and a half bath townhome unit with (shared) dock access. A lovely screened in porch dining area for cooking up the crabs you'll catch right off the dock and enjoying with family and friends, you're sure to be comfortable here! On the ground floor you'll find the comfortable living area with plush new furniture, a fully-equipped galley-style kitchen (electric range, refrigerator, dishwasher, microwave), a dining area with table, a utility closet with a washer and dryer, and a half bath/powder room in the hallway. Upstairs you'll find the bedrooms - a master suite with queen bed and a full bath. The other bedroom upstairs boasts a balcony with a beautiful view of the salt marsh below. For sleeping arrangements you'll find a bunk (a full on the bottom and a twin on top - always fun fighting over who gets that one!). Another twin is also located in the second bedroom as well. A full bath is located in the hallway upstairs. If you look to the grassy grove across the street you'll be looking at the location of the former Beebe Ranch, home of Misty of Chincoteague. You can almost see the little pinto paint filly frolicking through the paddock. Sit on the bench at the end of the dock with a cocktail or a cup of coffee at sunset and feel the cool island breezes coming off of the inlet and Curtis Merritt Harbor, just a little further down the road. Ride into town to get a bite to eat, or grab a few ingredients at one of our local seafood markets (a wonderful fishmonger and lobster lady lives just across the street) to make something easy at home. No matter what you decide, make a point to enjoy yourself at Marsh Point.

- 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.

Seas the Day

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Screened Porch
Pool
Internet

You will LOVE the quiet duplex community where this home is situated. Bright, open floor plan, with adjoining screened and open-air porches - perfect for sipping coffee in the morning or relaxing with a cool drink after a day at the beach. The first floor bedroom offers a private bathroom and the sweetest window nook - bring your book! Two additional bedrooms upstairs share a full bathroom and all bedrooms are tastefully decorated in their own fun personal themes! Hosting a group that requires more space? Rent Seas The Day's sister, 'Sea La Vie', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bunk bed + a Twin Trundle bed!**

- 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.

Touch of Grey

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Internet
Outdoor Shower

Welcome to "Touch of Grey," a delightful waterfront rental that blends comfort, style, and convenience into a perfect living space suitable for a variety of lifestyles. This well-appointed house includes three bedrooms, two bathrooms, and a range of updated amenities that ensure a seamless living experience.

Inside, discover a thoughtful layout featuring smart TVs throughout, high-speed WIFI, and a mix of privacy and social spaces that cater to both relaxation and entertainment. The screened porch offers a serene retreat, perfect for enjoying the outdoor air without the bother of pests, and the open deck invites you to bask in the stunning views that surround you.

Step outside to explore the  outdoor space that this property generously offers. A large deck overlooks the tranquil waters, ideal for peaceful mornings or lively evening gatherings. The highlights of the outdoor area include a personal boat dock, which provides immediate water access for boating enthusiasts. Meanwhile, the fire pit setup paves the way for memorable weekend cookouts with friends and family. This home also provides 6 bikes for guest use! 

Pet-friendly provisions mean that your beloved animals are just as welcome as you are, making it a true home for everyone. Functional features are balanced with aesthetic touches to create an inviting environment throughout.

"Touch of Grey" not only promises a picturesque setting but also ensures practicality with its various updates and amenities. Whether you’re drawn to the waterside way of life or simply seeking a tranquil place to call home, this property addresses all facets of modern living. Experience the blend of natural beauty and contemporary comforts in a place ready to be called home.

- 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 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.

Sunset Bay Villa 221

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

Buckle up, folks, because Sunset Bay Villa 221 is here to light up your vacation! This fresh-faced beauty just hit the market and is ready to become your new home away from home. Prepare to be blown away by water views so gorgeous, you'll want to frame them! Every nook and cranny of this place has a view that will leave you breathless.

The open floor plan allows you to cook and entertain at the same time. And let's not forget the deck, the perfect spot to kick back and enjoy your morning cup of coffee or unwind with a glass of wine as the sun sets over the water. The primary bedroom is fit for royalty with a king-size bed to cocoon you in comfort. But wait, there's more! Two additional rooms, one with a king, one with two twin beds, so everyone can sleep tight and dream big. There are tv's in each bedroom as well. Don't miss out on this gem! The Sunset Bay Villa Community has an outdoor pool, indoor workout room, and outdoor 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.

Horseshoe Hideaway

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Gas Grill
Screened Porch
Internet

Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a back road, fully enclosed by a fence, and ensconced by a generous yard and mature wooded area. With all the convenience of traveling around the island with ease, this home allows guests to drive or bike to Maddox Blvd, the beach or to the Main Street shops within minutes. Enjoy the outdoors on the fully screened in porches located on both the front and the back of the home, or take advantage of the generous back deck (accessed by a ramp or stairs) and supplied with a large gas grill, picnic table and Adirondack chairs. Inside the home features 3 bedrooms and 2 full bathrooms, a separate dining room, living room and eat in kitchen. There are several seating areas where guests can spread out or congregate as a group. The home is appointed with everything you need to enjoy a vacation at the Beach. This cute-as-a-button rancher home is waiting for your family vacation! Clean, comfortable and modest best describe the single-level home; there's an open kitchen, living and dining area that opens up to a front AND back screened porch. Enjoy all of the outdoor space from one of the 2 screened porches, or the spacious back deck and back yard! Located on a side street just off of Ridge Road, 'Horseshoe Hideaway' is conveniently located just minutes from downtown Chincoteague, as well as the "Beach Road." Come and check it out for yourself!

- 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.

Assateague Overlook

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water View
Charcoal Grill
Internet

This property has a location that is rich with views and 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. 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 (upstairs) has two twin beds and you'll find another full bathroom on the second level as well. Need more space? Rent Channel Lookout next door! (Waterfront area, dock, pier and playground equipment pictured are community property at Memorial Park.)

- 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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