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Mermaid Hideaway

1 Bedroom
1 Bath
4 Guests
Cape Charles
Internet

Escape to the Eastern Shore and discover a delightful coastal retreat that perfectly blends charm, comfort, and convenience. This one-bedroom, one-bathroom rental offers a refreshing getaway experience just minutes from the beloved Cape Charles Beachfront, making it an ideal home base for those seeking sun, sand, and seaside living.

Step inside and prepare to smile. The interior showcases a vibrant mermaid-inspired, tropical décor scheme that brings instant warmth and personality to every corner. Bold colors and playful accents create an atmosphere that feels less like a standard rental and more like a curated coastal escape. It is the kind of space that puts you in vacation mode the moment you walk through the door.

While the home comfortably serves as a cozy retreat for couples or solo travelers, it also accommodates up to four guests thanks to a convenient pull-out sofa bed in the living area. This thoughtful feature makes it equally suitable for small families or friends exploring Virginia's stunning Eastern Shore together.

Situated on the peaceful outskirts of Cape Charles, the location strikes a wonderful balance between tranquil seclusion and easy access to everyday essentials. A well-stocked grocery store is just a short drive away, and the iconic Chesapeake Bay Bridge-Tunnel provides a scenic gateway to the greater Hampton Roads region. Whether you are drawn to waterfront dining, charming boutique shopping, or lazy afternoons on the beach, everything the area has to offer remains comfortably within reach.

This affordable gem delivers an experience that far exceeds expectations. Book your coastal getaway today!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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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Grandma's House

4 Bedrooms
3 Baths
12 Guests
Chincoteague Island
Gas Grill
Screened Porch
Internet
Outdoor Shower

Introducing a charming and newly renovated home on Chincoteague Island!  Grandma's House is a delightful residence, boasting four cozy bedrooms, including two primary bedrooms conveniently located on the first floor, each designed for comfort and ease. With three well-appointed bathrooms, including a walk-in shower, the home is designed to cater to your relaxation and convenience needs. Grandma's House also has a handicap ramp for your convenience!

Step into the culinary paradise of a beautifully kitchen, complete with a sleek tiled backsplash, where both seasoned and aspiring chefs can whip up delectable dishes. Connected seamlessly to the dining area, this kitchen is perfect for gatherings and feasts.

Family fun is never in short supply thanks to the inviting den, complete with an air hockey table and darts for a bit of friendly competition. The screened porch offers a breezy retreat for evenings, while the spacious patio is set with both a gas grill and smoker for those sunny weekend barbecues. The heart of this home is undoubtedly its wide-open outdoor space, complete with a basketball hoop for the sports enthusiast and a front deck that invites you to enjoy your coffee while the morning breeze gently brushes against your face.

Whether you're entertaining guests or enjoying a quiet afternoon, this home ensures you can make the most of every moment. So come by and see why this isn't just any house — it's a vibrant living space waiting to be called 'home'! Here's a fun bonus — this home is attached to a charming apartment affectionately known as "Grandpa's Cottage," which is available as a separate rental. Rent them together for a larger group!

- 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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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. 

- *NEW FOR 2025: Level 2 EV charger!*

- 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. Small dogs only, restricted to two (2) pets. 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.

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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.

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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.

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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.

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Grey Heron

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

Majestic views await you from every room at Grey Heron, a charming raised contemporary located on North Main Street. Enjoy the unparalleled island sunsets from the private dock, spacious screened in porch and dining area, or with it's floor to ceiling windows and numerous cozy seating areas - from anywhere else in the home! Vintage artwork from local artist Hall Lott, known for his cover artwork for the Chincoteague Island Easter & Decoy Festival and Pony Swim posters, adorn the walls at every turn. Plush, cozy furniture in the living area as well as a round-about room featuring stunning 180-degree views of Chincoteague Bay and salt marsh give you plenty of space to enjoy company comfortably. A fully equipped kitchen (range, dishwasher, refrigerator) to prepare meals for family and friends, which is connected to the great room featuring a beautiful working fireplace and natural wooden floors. Grey Heron features 3 bedrooms, each boasting their own private balcony. On the upper level (accessible by the spiral staircase in the great room) you'll find the master bedroom - with the largest balcony, overlooking the sweeping vista of the bay and marsh. A comfortable king sized bed and television, as well as a full bath. The floor to ceiling bay window delivers plenty of natural island sunshine into the bedroom. Downstairs you will find the other two bedrooms - both with queen sized beds, a small balcony, and a cozy sitting area with view of the bay and marsh. Bring your bushel basket and crab right off the dock, then enjoy the bounty of the Chincoteague Bay from the screened-in porch. Bring your kayaks as well and launch them right from the private launch found off the bulkhead on the property. An outdoor shower to hose off after a sandy day at the beach. Plenty of space outside to enjoy family activities, and pet-friendly so bring your furry friends - they love basking in the sun on the dock as much as people do!

- 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.

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Grandpa's Cottage

1 Bedroom
1 Bath
2 Guests
Chincoteague Island
Town & Country
Internet
Outdoor Shower

Cute, clean, and chic — this cozy one-bedroom, one-bathroom studio apartment has everything you need for easy island living on Chincoteague. Whether you're looking for a seasonal escape or a place to call your home away from home, this little gem delivers big on charm without the fuss.

Step inside to find a full kitchen ready for your culinary adventures — from simple morning coffee to a full-blown seafood feast after a day at the beach. Full laundry is conveniently right on-site. It's the kind of place where you can kick off your sandals and just breathe.

Conveniently located near the carnival grounds and South Main Street, you're never far from the heart of island life. Veteran's Memorial Park is just a short stroll away for those peaceful morning walks. Need groceries? Island Foods Great Valu is right up the road. Feeling adventurous? Maui Jack's Waterpark and the stunning Assateague Beach are both within easy reach for endless fun in the sun.

Here's a fun bonus — this apartment is attached to a charming property affectionately known as "Grandma's House," which is available as a separate rental. Rent them together for a larger group or keep things simple and snag just this spot for yourself.

Island living doesn't have to be complicated. Sometimes all you need is a cozy space, good vibes, and the sound of the ocean breeze. Come see what Chincoteague living is all about!

- 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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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.

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Minchew

5 Bedrooms
3 Baths & 1 Half
12 Guests
Cape Charles
Town & Country
Pet Friendly
Screened Porch
Internet

Welcome to this charming new rental Minchew, a delightful 5-bedroom, 3.5-bathroom house that mixes modern amenities with cozy, family-friendly comfort. This home features a bonus space perfect for the family to spread out, and a welcoming fireplace in the living area perfect for chilly evenings. Upon entering you are greeted with a spacious living room, formal dining room, the kitchen has an eating nook and a desk. Home features an open concept living area that leads out to a great screened in porch where you can dine Al Fresco. You will find a suite on the first floor with a walk-in shower and a soaking tub, and the rest of the bedrooms are located upstairs.  The front porch adds to the home's appeal, providing a quaint space to enjoy the neighborhood's friendly atmosphere.

 

Residents will appreciate the very convenient location, offering abundant outdoor activities including trails and picnics with scenic views. Daily errands are a breeze with a local grocery store, Food Lion, less than two miles away, ensuring everything you need is always within reach.

 

This home is not only about comfort but also practicality, and a location near the beach that makes it ideal for those who love the ocean. The property is also pet-friendly, acknowledging the important role pets play in many families..

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly with an additional fee of $150.  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.

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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.

 

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Farmhouse Sunrise

3 Bedrooms
2 Baths
8 Guests
Cape Charles
Town & Country
Gas Grill
Internet

New vacation home listing! Completely renovated and ready to impress, this inviting three-bedroom, two-bath rental offers comfort, flexibility, and a location that makes everyday living refreshingly convenient. Designed with boaters and coastal beach enthusiasts in mind, the home sits just minutes from the Chesapeake Bay, giving you quick access to the water without turning every outing into a full expedition.

Inside, this upper-level residence feels fresh and updated, with renovations that bring a clean, polished look throughout. The layout is well-suited for a variety of living arrangements, and the duplex configuration adds versatility for those needing extra room. For larger groups or extended stays, there is even the opportunity to rent both the upper and lower portions, creating a practical setup with space to spread out.

Outside, plentiful parking is a standout feature, especially for tenants with multiple vehicles, a boat, or visiting guests. Convenient highway access makes commuting and weekend plans simple, while nearby essentials add to the home’s everyday appeal. The location also offers a practical route toward the Chesapeake Bay Bridge-Tunnel, helping regional travel feel a bit less complicated. Royal Farms is close by for fuel and quick stops, and Food Lion is within easy reach when it is time to stock the kitchen.

Whether you are seeking a comfortable new vacation spot, a well-placed coastal retreat, or a flexible rental near the bay, this home checks the boxes with ease and a little style to spare. 

- 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.

View Details

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