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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.

Joint Venture

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Water View
Pet Friendly
Internet

Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll to Maddox Blvd (Beach Road) and enjoy ice cream, mini golf or any of the shops & restaurants. Bike or drive to the beach! Joint Venture offers a water view of Little Oyster Bay (tidal creek) that can be enjoyed any time of year. This property offers Wi-Fi and is pet friendly! Don't miss out!

- 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.

Donovan's Reef

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

Charming Chincoteague coastal cottage doesn't even begin to describe this place, but it's a start. Cheery, bright, and colorful - with some form of island history gracing every nook and cranny. Find the perfect mix of old and new in this unique home. Close enough to the main drag on Maddox Boulevard and Main Street - but out of the hurly-burly here on Ocean Boulevard. Wake up a few minutes before everyone else and head across the street to get fresh donuts from Mister Whippy or chocolate croissants from Amarin to surprise everyone with. You'll be the hero for the day, until someone else brings home oysters that night. Oh, and bring your furry friends along, because this one's PET FRIENDLY! This property features lots of nooks for sleeping spaces - a loft upstairs, featuring skylights that let the bright island sunshine flood in. Up here you'll find a cozy king size bed in one room, and two twins in another, with a full bath that features a gorgeous tiled stand up shower. Downstairs you'll find two more bedrooms - one with two twins, and the other with a king. Three different comfortable living areas, one of which is an outdoor sunroom - and that room has doors that connects to the downstairs king - in addition to the main living area. Small backyard area for letting the puppies play or eating lunch outside at the picnic table. The retro mid-century kitchen has everything you'll need to prepare that island seafood dinner with what you catch down at the town dock, and a lovely dining area to enjoy it as a family. Donovan's Reef is located in the heart of downtown Chincoteague, allowing you an easy walk to all the shopping the island has to offer. Stop by Chincotiki on your way home and grab an orange crush or two!

- 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.

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.

- Home is pet friendly with additional pet fee. 

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

Eastside Escape

4 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Town & Country
Gas Grill
Screened Porch
Internet

Discover the perfect blend of comfort, convenience, and coastal charm at 'Eastside Escape', a beautifully updated vacation home ideally located in the center of Chincoteague Island. Whether you’re here for wild pony sightings, beach days on Assateague, or simply to unwind in a peaceful seaside town, this home offers the ideal setting for your getaway!

Step inside and you’ll find a bright, welcoming interior designed for relaxation. The cozy living area invites you to kick back after a day of exploring, while the fully equipped kitchen makes it easy to prepare your favorite meals. Thoughtful touches throughout the home provide the comfort of modern amenities with the warmth of traditional island style.

Featuring four spacious bedrooms and two full bathrooms, this home provides plenty of room for families, couples, or small groups—offering privacy and comfort for everyone in your group. The outdoor space is just as inviting: enjoy morning coffee on the porch, gather for an evening barbecue, or unwind under the stars after a day at the beach.

Conveniently located on Church Street, you’re moments from everything that makes Chincoteague special: charming downtown shops, cafés, and restaurants; the waterfront and iconic sunsets; bike paths and nature trails; Assateague National Seashore with its beaches and wild ponies, and so much more!

Whether you’re seeking relaxation, adventure, or a little of both, 'Eastside Escape' offers the perfect home base for your island getaway. Book your stay today and experience the magic of Chincoteague—from a home that feels like your own.

- 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.

Tall Pines

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

Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room. Tall Pines has two bedrooms, one with a queen, and other featuring two twins. There is also an air mattress for guest use.  Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall Pines is pet friendly with and outdoor dog run in the yard. You won't be disappointed! | | Note: Water access is a shared with the community just a short distance from the rental home.

- 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.

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. 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.

Hailey's Round House

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Screened Porch
Internet

Check out Chincoteague’s newest Piney Island vacation rental! Hailey’s Round House is in a prime location on Chincoteague, in a quiet development road but just a short walk to the bridge to Assateague and the Maddox Boulevard shops and restaurants!  You could take a bicycle or short drive to the Assateague beach and access to all of the bicycle trails around Chincoteague and Assateague to enjoy the wild ponies or many of the restaurants on Chincoteague.   

Hailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed.  You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay! 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

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

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.

Sunset Bay Villa 116

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pool
Internet

A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy tiled shower and whirlpool bath. Villa 116 will sleep 8 (beds for 6 plus a queen size air mattress), and includes a full laundry, all appliances, a gourmet kitchen, and more. There's also a pool and fitness room for your enjoyment! Tastefully furnished, you can relax, enjoy and entertain your family and friends in style. | NOTE: This unit does not have a boat slip, however, use of the marina is included.

- 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.

Stella della Baia

2 Bedrooms
1 Bath
5 Guests
Chincoteague Island
Charcoal Grill

Welcome to 'Stella della Baia'! This is the perfect little getaway spot if you're looking for something simple, comfortable, clean and affordable. Everything is BRAND NEW and waiting for you! Located just south of downtown, Stella della Baia is conveniently located to the Fireman's Carnival, movie theater, downtown restaurants & shopping, and more. If you're traveling with a larger group but like the separate of "your own place", check out 'Stella del Mare'! Book both homes and receive a 5% discount off of each! 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pets are not 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.

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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