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Oyster Shack

3 Bedrooms
2 Baths & 1 Half
8 Guests
Cape Charles
Town & Country
Pet Friendly
Internet
Outdoor Shower

Introducing the newest gem in Cape Charles! Perfect for those seeking a serene retreat, this charming vacation rental boasts three cozy bedrooms, including a spacious primary bedroom, complemented by two and a half well-appointed bathrooms. Nestled in the heart of town, this delightful home invites comfort and exudes modern elegance.

Step inside to discover a beautifully crafted layout where each square foot is maximized for enjoyment and ease. You'll love the convenience of your own peaceful backyard, ideal for morning coffees and evening relaxation. Plus, it’s a pet-friendly haven, so your furry friends can join in on the fun!

Staying here, you're seconds away from sinking your toes in the beautiful beach, ensuring endless days of sun-soaked adventures. Need a break from the sun? Dive into the refreshing experiences available at the nearby at Cape Charles Mini Golf!

For those who love cooking with fresh ingredients, the local Beach Market is just a short trek from your doorstep, making it nearly effortless to gather necessities for a spontaneous beach picnic or a cozy family dinner.

Whether you’re in for a weekend getaway or a longer relaxing stay, this house is more than just a place to stay—it’s the backdrop for your next chapter of cherished memories! Ready to kick off your sandals and stay a while? This Cape Charles beauty is waiting to welcome you! 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee of $150 per pet. All pets must be disclosed prior to arrival. 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.

 

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.

- Pets are permitted with an additional fee of $150 per pet. Limit of two dogs only. All pets must be disclosed. 

- 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. A pet 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.

Piney Island Paradise

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

Welcome to Piney Island Paradise! This well-furnished townhouse is nestled in a secluded cul-de-sac along East Side Drive and offers some of the best views of Assateague Island and the historic lighthouse located across the channel. The channel on Eastside offers some of the calmest water for kayaking, plentiful crabbing, and great fishing. Enjoy the most beautiful sunrise views from this vacation home along with quiet solitude! This home also offers 2 kayaks for your enjoyment! 

Upon entering this home, you will find a half bath, first floor bedroom with a queen-sized bed, a well-stocked kitchen, living room, and large waterfront deck with plenty of seating to relax, enjoy the wildlife, and watch the ponies grazing on Assateague Island. On the 2nd floor you will find two more bedrooms as well as the laundry area. The main suite features a king-sized bed with a full bathroom and waterfront deck to enjoy the peaceful sounds of nature and beautiful sunrise views. You will also find a 3rd bedroom that easily accommodates 5 more guests. This room features a twin over twin bunk, a twin over full bunk, and a full bathroom with walk in shower. This home also includes a nice assortment of beach chairs and a small attached garage where you can store your bicycles and kayaks. If you are looking for a home with all the amenities and want to enjoy the beauty of Chincoteague & Assateague Island, this is it!

- 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.

Sunset Bay Cottage

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water View
Pet Friendly
Gas Grill
Internet
Outdoor Shower

Experience island living at its finest in this beautifully restored Victorian home on North Main Street. This 3 bedroom, 2 bathroom rental offers the perfect blend of historic charm and modern comfort. The enchanting enclosed front porch provides the ideal setting for your morning coffee while watching the town come to life.

Step inside to discover a thoughtfully renovated interior that maintains the home's original character while incorporating contemporary amenities. The first floor features the living room with a sleep sofa and full bathroom, while the second floor hosts two bedrooms (each with a Queen bed) and another full bathroom. The entire third floor is a loft-style bedroom that houses a Double + 2 Twin beds. 

One of the property's most captivating features is its magnificent water views of Chincoteague Bay. Imagine ending each day with spectacular sunset vistas painting the sky in brilliant hues of orange and pink. The location couldn't be more perfect — situated across from a waterfront park, you'll have easy access to outdoor recreation.

The carefully landscaped backyard creates a private retreat with a dedicated sitting area perfect for afternoon reading or evening conversations. Enjoy s'mores in the evening over the fire pit. The spacious deck extends your living space outdoors, ideal for entertaining or simply soaking in the island atmosphere.

Located in the heart of Chincoteague, you'll be within walking distance to Island Nature Trail and a short drive to local attractions including Maui Jack's Waterpark and the renowned Chincoteague National Wildlife Refuge & Beach.

This isn't just a house—it's an invitation to embrace the relaxed coastal lifestyle that makes Chincoteague so special. Ready to write your own chapter in this charming island home? Come and see for yourself!

Special Note: The stairway to the third level is narrow and steep. There are adult bicycles and beach gear for guest use. 

- 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). 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.

 

Crabby Pines

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

Discover comfortable vacation living in this charming one-level ranch home. "Crabby Pines" offers a cozy retreat with three bedrooms and two bathrooms, providing ample room for relaxation and privacy. The house is ideally situated in a serene residential neighborhood and features modern amenities that ensure a seamless, convenient lifestyle.

Enjoy the convenience of being just minutes away from the public boat ramp at Fur Landing. Outdoor enthusiasts will appreciate the close proximity to nature trails and a dog park, perfect for morning jogs or leisurely evening walks with your furry friends. Oh, did we mention this home is pet friendly? Additionally, the property is located near the 'Beach Road,' a vibrant area bustling with mini-golf, dining options, ice cream shops, and boutiques - offering endless entertainment options.

This welcoming home is designed with practicality in mind, ensuring that each space is utilized efficiently while still exuding a sense of warmth and comfort. The property's easy access to local amenities, combined with its peaceful surroundings, makes it an ideal choice for anyone looking for a balance between nature and community activities.

Whether you're settling down with family or looking for a tranquil spot to return to after a day of adventures on the island, this home is sure to meet your needs. Embrace a laid-back lifestyle in Chincoteague with this delightful vacation home opportunity.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This home is pet friendly with an additional fee. Maximum of two dogs under 25 lbs. each; 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.

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.

Sun Rayes

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

We welcome "Sun Rayes"! What does this fabulous home have to offer? The question is: what doesn't it offer?! With 4 bedrooms, 3 bathrooms, 3 stories (with an elevator), a game room (ping pong, pool table, dart board, ring toss) and expansive decks - there's room for everyone! Situated on a canal in the popular Captain's Cove community, you have access to a boat ramp and you can dock your boat right outside your door! Also perfect for fishing, crabbing, kayaks, etc. Sun Rayes is packed full of fun - there are so many great spaces for entertaining and relaxing. The Captain's Cove community offers 3 pools (2 outdoor & 1 indoor), tiki bar, Marina Club and restaurant, 9-hole golf course, kids playground, dog park and more! (amenities are available for use with fee)  And you're only 20 minutes from Chincoteague & Assateague Islands (the beach), and 30 minutes from Ocean City, MD (boardwalk & amusements).

- 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. Pet restriction: 2 pet max.

- 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. 

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.

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.

The Lighthouse

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Waterfront
Boat Dock
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

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.

Sunrise/Sunset

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Town & Country
Gas Grill
Internet

Looking for an island home that won't drain your savings? This two-bedroom, two-and-a-half-bathroom townhouse delivers comfortable Chincoteague Island vacationing with a price tag that actually leaves room for ice cream cones and beach days.

The heart of this home is its standout four-season room, a bright and breezy spot built for year-round enjoyment. Curl up with a book in the dead of winter or throw the windows open when the salt air calls — either way, you'll find yourself drawn back to this cozy corner again and again. An electric fireplace adds a flicker of warmth to chilly evenings, perfect for unwinding after a day of island wandering.

Both bedrooms sit upstairs, tucked away from the main living areas for a little extra peace and quiet when it's time to rest. Step outside and you'll discover a fenced yard, ideal for letting pets roam, hosting a casual cookout, or simply claiming your favorite lawn chair under the open sky.

Location? You've hit the jackpot. Veteran's Memorial Park is practically next door, complete with a playground, courts, and plenty of green space. The annual Carnival is just around the corner for summertime fun, while Island Foods handles grocery runs in a flash. When adventure calls, Maui Jack's Waterpark and the legendary Assateague Beach — wild ponies included — are a short hop away.

Affordable, comfortable, and perfectly positioned. What are you waiting for?

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Pets (dogs only) are permitted with an additional pet fee of $150 per pet. 

- 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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