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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.

Blue Point

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

Come for an old fashioned family vacation. This wonderfully maintained classic Chincoteague-style home features a large screened porch and beautiful, spacious yard for those warm summer evenings. A great enclosed outside shower comes in handy for rinsing the sand off after a long day at the beach. Downstairs there is a family room with a wood stove, living room/library with a TV and an eclectic selection of books, a formal dining room, full bath and kitchen. Upstairs there are three bedrooms and a full bathroom. Bring your kids and pets along, there is plenty of room to play!

- 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.

Gone Coastal

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet

Enjoy the cool breezes coming off the Chincoteague Channel while relaxing on the porch at Gone Coastal! Nestled in a grove of pines and tucked just off East Side Drive, this charming unit has everything your family desires for a wonderful stay on Chincoteague Island. Bright and cheery nautical decor will help to put you on "island time". Featuring two bedrooms, two and a half baths, a spacious living and dining area, and a fully-equipped kitchen. The two bedrooms are on the upper level. The master features a full bed with flat screen television, full bath, and balcony with sliding door and comfortable outdoor furnishings. An additional bedroom featuring a full size bed and double bunk, and a full bath is located in the hallway upstairs as well. On the ground floor you'll find a spacious living area with large flat screen tv, plush seating, and plenty of reading material. The eat-in kitchen features everything you'll need to prepare and enjoy meals "at home" - electric range, roomy refrigerator, dishwasher, coffee bar, and dining table. A full-sized washer and dryer are located in a utility closet just off the kitchen, and a barbecue grill is located on the back porch for your convenience. Located centrally on the island - you're a quick bike ride or easy walking distance to the commerce on Maddox Boulevard or downtown Main Street, or to Memorial Park located just down Eastside Drive. Pop into one the oyster farms and grab a sack to bring back and enjoy with a glass of wine as the sun sets on another day Gone Coastal. Please Note: No boats or trailers are allowed at the complex.

- 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.

Fisherman's Cottage

1 Bedroom
1 Bath
4 Guests
Chincoteague Island
Town & Country
Pet Friendly
Gas Grill
Internet
Outdoor Shower

Welcome to this fabulous, cozy retreat on Chincoteague Island! The charming one-bedroom, one-bathroom cottage offers the perfect getaway for up to four guests, and you can bring Fido as well!

Nestled in a quiet location, this delightful home puts you within easy reach of the town's attractions, Beach Road (Maddox Blvd.) the Assateague Lighthouse, Memorial Park and even some wonderful eateries. After a day of exploration or relaxation at the beach, unwind on the screened porch, where you can sip your favorite beverage and listen to the soothing island sounds. Fancy a bit more outdoor living? Fire up the gas grill and enjoy a delicious meal on the patio. It's the perfect spot for swapping stories and making memories under the stars.

Inside, you'll find a tastefully remodeled space that's clean, cute, and comfortable. The house comes equipped with all the modern luxuries you need for a stress-free stay. Coffee lovers, rejoice! You have your choice of a drip pot or Keurig machine to kickstart your mornings. The primary bedroom offers a Queen bed and a peaceful sanctuary for rest, while additional sleeping arrangements (Double-size sleep sofa in the living room) ensure everyone has a comfy spot to drift off to dreamland.

Whether you're here to spot the famous Chincoteague ponies, visit the Assateague Island Lighthouse, or simply soak up the laid-back island vibes, this rental has you covered. It's just a hop, skip, and a jump from local hotspots like Memorial Park! So, pack your flip-flops and your sense of adventure – this little slice of island paradise is waiting for you. Just remember, what happens on Chincoteague stays on Chincoteague... unless, of course, you can't resist posting those amazing vacation pics!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This home is pet friendly - DOGS ONLY - 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.

Admiral Benbow

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

A very nice contemporary home located in Oyster Bay I community. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner! The variety of bed sizes allow the perfect set up for families of all ages! Come and stay at this classic Chincoteague home but don't delay; it books quickly!

- 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.

High Tide

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet
Outdoor Shower

We're pleased to be able to offer 'High Tide' as one of our most popular vacation rental selections! The true epitome of a beach house, you'll enjoy the bright, cheery decor and spacious feel of this fabulous home. The downstairs features an open living room (with fireplace and flat-screen TV), dining area and kitchen, as well as over-sized windows and access to the two (yes, TWO!) screened porches. One porch features a wonderful dining set; perfect for dining al fresco. The second spacious porch features a large hammock and nice sectional lounging sofa. As if that's not enough outdoor space, there are also multi-level, open air decks on the front and back of the home! There's also a bedroom (king) and full bathroom downstairs. The upstairs features two additional bedrooms (one with a queen & two twin beds, and the other with a queen & one twin bed), and a full bathroom. Both upstairs bedrooms are enhanced by sliding doors and private balconies. You'll enjoy snippet water views of the Assateague Channel! Don't delay, 'High Tide' books quickly. Please note: As part of the Piney Island Community, this rental includes water access at a shared community location just a short distance from the home.

- 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.

Junxtion

4 Bedrooms
3 Baths
10 Guests
Cape Charles
Charcoal Grill
Internet
Outdoor Shower

Introducing a captivating vacation home within the charming environment of Cape Charles, VA. This expansive four-bedroom, three-bathroom residence offers a unique blend of classic charm and modern elegance, recently transformed from a duplex into a single, large family home. Situated on a generous corner lot, this property provides ample street parking suitable for boat trailers and features delightful outdoor amenities including a shower, deck, fire pit, grill, and a spacious front porch.

The interior is a testament to meticulous craftsmanship and design. The open-plan first floor anchors the home with a grand gourmet kitchen, fully outfitted with all essential appliances and perfect for culinary enthusiasts. Adjacent to the kitchen, the dining area comfortably seats ten, complemented by a cozy coffee corner and a musical nook equipped with a guitar and microphone—inviting impromptu jam sessions.

Venture further to discover double French doors that reveal an ultra-cool TV room adorned with a personal vinyl collection. A convenient laundry and bathroom complete this level. The second floor boasts two queen-sized bedrooms and a thoughtfully appointed study. Enjoy the comfort of a large California king bedroom, designed with luxurious seating to provide a haven of relaxation.

The home’s crown jewel is the third-floor primary bedroom suite, which includes one king bed, two twin beds, and a sofa bed. A full bath features a large shower and a double slipper Victorian bath, enhancing the spa-like atmosphere. Blackout blinds in all bedrooms ensure a restful night's sleep.

This home is located within walking distance of the pristine Cape Charles Beachfront and a short stroll from the historical delights of the Cape Charles Historic District. Commuting is made easy with proximity to the Chesapeake Bay Bridge-Tunnel. Offering more than just a place to stay, this property encapsulates a meticulously curated lifestyle, infusing a London chic with the serene backdrop of historic Cape Charles. Experience the culmination of a decade’s worth of dedication and a heartfelt invitation to make lasting memories in what can truly be called a dream home.

- 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.

Charlie's Cove

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Pet Friendly
Internet

Charlie's Cove is waiting to accommodate you and your guests! Conveniently located on Ridge Road in the middle of Chincoteague Island, you will find yourself immersed in complete comfort. Upon stepping through the door you are greeted by the simple, yet welcoming décor. An oversized couch is sure to relax you after a long day in the sand, cuddle up and watch a movie or play a board game! Charlie's Cove has it all... The kitchen is perfectly designed, offering an abundance of place for the cook in your family to prepare meals. There is a private den if you'd like to spend some quiet time away from the group. This home offers 3 large bedrooms - the primary features a Queen bed and en suite bathroom with large soaking tub and stand-alone shower. The second bedroom features another Queen bed, while the third bedroom has 2 Twin beds. Bring your furry friend to run in the fenced in yard - Charlie's Cove is pet friendly!  

**While this home will accommodate up to 8 guests, there is only sleeping space for 6 (2 Queen beds and 2 Twin beds). Please feel free to bring an air mattress or cot. 

- 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.

Blue Chair Bay

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

If you're looking for a little slice of paradise at the beach, look no further! This delightful townhome is adorned with beachy, Kenny Chesney vibes throughout! As Kenny Chesney sings, "There's a blue rocking chair, Sittin' in the sand, Weathered by the storms and well oiled hands, It sways back and forth with the help of the winds, Seems to always be there, like an old trusted friend." Enjoy all of the outdoor space - from the 2 level waterside screened porches, to the covered parking area with picnic table - there's plenty of room for all to enjoy. The downstairs features the kitchen and dining area, a half bathroom, living room, and expansive screened porch. Upstairs you'll find 3 bedrooms; one of them a master suite with private bathroom. There's also another full shared bathroom off the hallway. The South Main street location offers some of the most beautiful sunsets you'll ever see. Watch the tide roll in, the boats sail by, and the dolphins play along the Chincoteague Bay. There's also a shared pier if you'd like to try your hand at fishing, or if you'd like to sit on the water and relax with a cup of coffee. Don't delay - these townhomes are very popular and book quickly!

- 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.

Charlotte's Morning Sun

4 Bedrooms
4 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Set in the boutique residential community of Oyster Bay I, 'Charlotte's Morning Sun' is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms, one of which has it's own balcony that feels like it's floating on water. The stylish design offers private and peaceful lounge and dining areas that embrace sweeping bay views that stretch uninterrupted to the horizon. A state-of-the-art chef's kitchen, a generously-sized waterside screened porch as well as a large observation area allows effortless indoor outdoor living. On the first level you'll find the living room, observation area, chef's kitchen, dining area, 2 bedrooms and a wonderful waterside screened porch. Upstairs you'll find 2 more bedrooms, one with a private balcony. Outside, enjoy exclusive access to the bay via a private dock/boat-slip, or bathe in the outdoor beach shower surrounded by a grassy coastal garden. Just a short drive to the beach, local restaurants and shops, 'Charlotte's Morning Sun' offers an opportunity to secure a luxury vacation home in an exceptional setting. Note: The Oyster Bay I community where this property is located offers a boat ramp that is exclusive to the homes in this community. Water depth may not be suitable for all boats and dock/ramp usability cannot be guaranteed. You can crab and fish at this community harbor area.

- SPECIAL NOTE: This rental home has a 5 night minimum during the off season. 

- 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.

Island Estate

5 Bedrooms
3 Baths
14 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

Fabulous, fabulous, fabulous! If you're looking for a large space to have a family vacation or reunion, this is it. This beautiful waterfront home is located on a tidal creek and boasts over 3,000 sq ft of living space. All amenities - central air, all kitchen appliances & washer/dryer, and so much more! The formal dining room is great for large gatherings. Beautiful back deck area with private pool for your enjoyment. Island Estate is a PET FRIENDLY home. Please Note: Pool is open Memorial Day weekend through end of season/last renter (weather permitting).

- 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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