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Charlie's Bayside Retreat

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

This is it! Are you looking for your perfect vacation getaway spot? Look no further. 'Charlie's Bayside Retreat' is everything you'll need for your home away from home, at the beach! The first main level features an open floor plan with a living room that opens up to a wonderful screened porch with comfortable outdoor dining furniture. The open living area also features a large Smart TV with cable and an electric fireplace. A modern kitchen that is fully stocked with everything you could possibly need, also has new appliances and a Keurig coffee maker, breakfast bar, open dining area, and powder room complete the first-floor living space. On the second floor, you'll find two bedrooms, one with a Queen bed and Smart TV and the other with 2 Twins & a Full - both with balconies and a shared full bathroom with dual sinks. The entire third floor is a spacious, private primary oasis with a Queen bed, and a luxurious en suite featuring a deep jetted tub and dual sinks. This bedroom is also equipped with a Smart TV and a balcony with amazing views & Adirondack chairs making it perfect for relaxing or sunbathing. Additional features of this fabulous vacation home include your own private boat slip (#7), pier for fishing and crabbing, fish cleaning station, covered parking area, grill, picnic table, and tons of extras! There's an outdoor shower, and beach gear including beach chairs, beach toys, and an umbrella. Not to mention you're conveniently located on South Main Street - walk to the downtown area (including Ropewalk for food and drinks) or to the annual Fireman's Carnival. The possibilities are endless. Some of the most gorgeous sunsets ever witnessed are from this spot on South Main Street & it is the perfect spot to watch rocket launches from Wallops. It doesn't get much better than this!

- 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.

Pony View

3 Bedrooms
3 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Internet

Enjoy your cup of coffee as the sun peeks over the salt marshes of Assateague Island. You can often see a herd of our famous wild ponies grazing to the right of the lighthouse from your private waterfront deck and second-floor balcony - not to mention the copious amounts of waterfowl and other wildlife in the channel. Pony View boasts three bedrooms - A master with queen bed, full bath, and balcony on second floor, as well as another bedroom with a queen on the second floor - along with another full size bath. On the third floor you will find an amazing view of the marsh with the panoramic window and four twin beds, and a beautiful bathroom with a rustic wooden sliding door. The ground floor is where you'll find the hub of the house - fully equipped kitchen with refrigerator, electric range, dishwasher, and plenty of counter space. A dining table and bar seating area, a half bath, and a cozy living area with floor-to-ceiling knockout views. Or enjoy the waterfront deck just outside the living room. Pony View is pet-friendly so your furry friend can enjoy the water view as well. Dock access along with a boat slip is available for your use. Crab and fish right from the house! A deep water boat ramp is found just at the end of the complex for you to drop in. Central air/heat will keep you comfortable year round. There is also a washer/dryer, and an outside grill for your use while you're with us. Memorial Park is just a short walk up the street for a wonderful waterfront park and playground, tennis and volleyball courts, fishing pier, picnic areas, and walking trail.

Please note: Parking is limited to 2 spaces (this includes a boat/trailer if you are bringing one). Max. boat size for docking is 20'. If alternate parking accommodations are needed, please ask. 

- 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.

Casa del Mar

5 Bedrooms
4 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Hot Tub
Internet
Outdoor Shower

Casa del Mar - "House by the Sea" - is your home away from home... at the beach! Located in the heart of downtown Chincoteague Island, this grand home has been lovingly maintained and is conveniently situated within walking distance to the waterfront park, boutique shops, restaurants, movie theater and coffee shops! Casa del Mar is one of our newest vacation rental offerings, and we know you'll love it! The spacious, open floor plan features a family room and kitchen, as well as a formal living room and plenty of outdoor space. There's a master bedroom en suite, and the bathroom features a tiled shower and jacuzzi tub. Outside you'll find the perfect backyard, complete with a grill, outside shower. Perfect for relaxing in the evenings after a long day at the beach! And you can even bring the 4-legged family members as well! Don't delay; this one will book quickly! Floor Plan: Downstairs features the living room, family room, kitchen w/ dining area, dining room, master bedroom (King bed & Futon) and full bathroom (shower only). Upstairs features 4 bedrooms - one with a King, one with 2 Queens, one with a Queen, and another with a Queen. The King bedroom and 2 of the Queen bedrooms have attached bathrooms (tub & shower). There is a 3rd upstairs bathroom w/ tub & shower off of the hallway.

- 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.

Shady Grove

4 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water View
Screened Porch
Internet

Come and relax at this fabulous beach home that is tucked away on the quiet northern end of Chincoteague Island! Aptly named, "Shady Grove" is situated in a natural marshland grove in the Richardson's Landing community. Features include 4 bedrooms, 2 bathrooms, numerous updates and remodeling and a bright, open floor plan. Come and see for yourself - you won't be disappointed!

- 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.

Shell Cottage

4 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water View
Pet Friendly
Gas Grill
Hot Tub
Internet
Outdoor Shower

Come and enjoy a delightful vacation at "Shell Cottage"! Located on the popular East Side of Chincoteague Island, you'll enjoy water views of the Assateague Channel and lounging on the outside decks (one which includes an outside shower). This open floor plan home features two bedrooms downstairs (both with a queen bed and a TV each), a half bathroom, and spacious living room & kitchen. Upstairs you'll find 2 more bedrooms (one with twin trundle and the other with 2 twins) and a full bathroom. Just a short drive to the Memorial Waterfront Park, public boat launch, downtown area and restaurants! Shell Cottage also includes all the modern conveniences such as wireless internet, washer/dryer, dishwasher and more. And you'll have room to park your boat and trailer. This just may be your perfect vacation spot!

IMPORTANT NOTE: The hot tub is closed 10/01/25, it will reopen Spring of 2026.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

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

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Windshadow

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

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

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

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

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Lottie's Lookout

3 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Pet Friendly
Internet

Come stay at this Chincoteague Island Charmer, better known as Lottie's Lookout! This large spacious home features 3 levels, with 3 large bedrooms, and 3 bathrooms. The first level features a front porch, pull out sofa, large dining table for family meals, and a full bathroom. Upstairs you will find 3 twins, (one bunk) and another bedroom down the hall with a queen sized bed. There is a full bathroom on this level as well. On the third floor, you have a full sized bed and bathroom with a tub (no shower). Enjoy the outdoors in the large yard, or grill up some good food from one of the many local markets. Lottie's Lookout is in a perfect location, close to the downtown area!

- 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.

Pocahontas

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Nestled in the vibrant heart of Cape Charles, this exquisite one-bedroom condominium represents bayside town living at its most refined. Recently transformed through meticulous renovation, the home seamlessly blends simplistic sophistication with coastal charm to create an atmosphere of understated luxury.

The thoughtfully designed interior showcases an open living space with a fireplace and large TV, sumptuous primary bedroom featuring a king-size bed that promises restful nights after sun-soaked days. Step through the doors onto your private balcony, where panoramic views of downtown and the marina create an ever-changing tableau of maritime activity and small-town vibrancy.

Culinary enthusiasts will appreciate the full kitchen appointed with premium new appliances, inviting both casual meals and ambitious dinner preparations. The custom-tiled bathroom elevates daily routines to spa-like experiences, reflecting the property's commitment to refined comfort.

Location defines true luxury, and this residence delivers magnificently. Mere blocks from the shimmering shores of the Chesapeake Bay, you'll find yourself effortlessly immersed in the coastal lifestyle. The convenience of having Cape Charles' most coveted attractions just steps from your door cannot be overstated—savor artisanal spirits at the local distillery, browse distinctive boutiques and art galleries, indulge in gourmet ice cream, or select from diverse dining options.

For the discerning individual seeking a harmonious blend of tranquility and accessibility, this sanctuary offers a rare opportunity to embrace the quintessential Cape Charles experience.

PLEASE NOTE: 'Pocahontas' 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 on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted. 

- 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.

Windsor House

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Gas Grill
Internet

Time to hit the road and get ready for a beachy retreat at "Windsor House"! The moment you step inside, you'll be dazzled by the vibrant colors that'll make you feel like you're in paradise! The spacious living room and kitchen are perfect for whipping up a delicious meal or hosting a fun-filled bash! The primary bedroom is fit for royalty with its king-sized bed, snuggly and inviting. And there's more! The two additional bedrooms have a queen and two double beds to cater to all your guests. And when you want to take things outside, you'll find a grill to cook up a storm and outdoor seating to enjoy the island breeze. Get ready to soak up the sun in style! Located off of Clark street, you are within close proximity of many restaurants, local shops, and a short drive to the beach!

- 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. 

 

Timeout

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

Welcome to your island getaway! This charming 2-bedroom cottage offers the perfect blend of comfort and coastal living. Lovingly renovated with care, this rental home captures the relaxed spirit of Chincoteague Island.

Step outside to enjoy the screened porch where you can sip morning coffee while listening to seabirds or unwind in the evening with a cold beverage. The inviting backyard is ideal for soaking up sunshine or enjoying a cookout on the gas grill.

Water enthusiasts will appreciate the kayak provided for exploring the island's scenic waterways. For land adventures, hop on one of the two bikes to cruise around town. When you're feeling competitive, challenge your companions to a friendly game of croquet or cornhole — all equipment included!

Your four-legged friends are welcome to join in the island fun, as this property is pet friendly.

Location is a true highlight! Just a short stroll away is the Downtown Chincoteague Waterfront Park, perfect for picnics and people-watching. For family adventures, Maui Jack's Waterpark offers splashy fun just minutes away. The crowning jewel of the area—Assateague Beach—is a quick drive from your rental, where you can witness the famous wild ponies and enjoy pristine shorelines.

Experience the casual, laid-back lifestyle of Chincoteague Island in this cozy home that's the perfect launch pad for creating unforgettable vacation memories!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

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

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Vast Views

2 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water View
Pet Friendly
Boat Dock
Pool
Internet

Welcome to your perfect coastal getaway in charming Chincoteague Island! This newly remodeled townhouse offers the ideal blend of comfort and modern amenities, featuring two cozy bedrooms and three full bathrooms as well as an open floor plan perfect for entertaining! Step into a space where everything sparkles with newness, from the stylish fixtures to the thoughtfully placed flat-screen TVs in every room. The innovative touches, such as bathrooms equipped with cutting-edge built-in Bluetooth speakers, make this home perfect for both relaxation and entertainment.

The location couldn't be better for beach lovers and adventure seekers. Step outside to enjoy exclusive community amenities like a swimming pool and a pier with direct water access to Assateague Channel. Try your hand at fishing or crabbing, or tie up your boat - there’s no better way to end your day than with mesmerizing water and lighthouse views right from your vacation home! The community pool provides a refreshing escape on warm summer days, while the nearby Memorial Park offers tennis courts and a playground for your enjoyment.

The East Side location could not be more ideal - when you're not in the mood to cook, local restaurants are just a short stroll away, serving up fresh seafood and coastal favorites. The area's attractions are sure to keep you entertained, with Maui Jack's Waterpark and the pristine Assateague Beach both within easy reach. Nature lovers can explore the famous wild ponies and abundant wildlife that make this island so special.

This townhouse isn't just a rental – it's your piece of paradise that offers the laid-back coastal lifestyle that Chincoteague is famous for. Whether you're seeking a peaceful retreat or an adventurous beach vacation, this home delivers the best of both worlds.

This pet-friendly home also offers the option to rent neighboring units, making it ideal for larger groups or family gatherings! Make this brand new townhouse your sanctuary on Chincoteague Island, embracing a blend of comfort, convenience, and natural beauty all around. Your island lifestyle awaits!

- 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.

Bayside Bliss

4 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Hot Tub
Internet
Outdoor Shower

Welcome to your serene retreat at Bayside Bliss! This stunning waterfront rental offers a perfect blend of tranquility and convenience, ideal for those who appreciate nature and outdoor activities.

Spanning four generously sized bedrooms and three full bathrooms, this home is a perfect fit for families or groups seeking both comfort and space. Enjoy preparing meals in a fully-equipped kitchen and dine al fresco on the enclosed porch while taking in the breathtaking water views. This space  provides a peaceful spot for morning coffees and cozy evenings alike. You will find one bedroom with a queen size murphy bed, and full bath on the first floor, with all other bedrooms located on the second floor. 

Outdoor enthusiasts will fall in love with the outdoor dock. Whether you’re a fan of boating, fishing, or simply enjoying a sunset over the water, these amenities ensure every day feels like a vacation. The gas grill makes outdoor entertaining a breeze, surrounded by ample deck space that welcomes gatherings under the stars.

The property's location enhances its charm. Nestled just minutes away from essentials, it is conveniently located close to everything you will need to make your vacation enjoyable.

This home not only promises a comfortable and stylish living arrangement but also proximity to local amenities and natural beauty. Embrace a lifestyle marked by peace and relaxation at this Chincoteague charmer. Ready to make it your temporary haven? Contact us today to book your reservation at Bayside Bliss!

- The home does have a hot tub in the enclosed porch but will not be available for this 2024 season.

- 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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