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Daisey Cottage

2 Bedrooms
1 Bath
7 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Internet

Come visit Chincoteague Island and stay in this adorable coastal cottage with your family. Lovingly remodeled and updated, this charmer located on Ridge Road is sure to book up fast! Close enough to hustle and bustle of carnival and downtown, but far enough away to enjoy some peace and quiet - you'll find all the comforts of home at Daisey Cottage. Upon entering you'll be greeted by a comfortable living area with television. Skylights to let in a ton of natural light, letting you bask in island sunshine. A cute kitchen featuring everything (electric range, fridge, dishwasher, coffee maker) you'll need to make a family meal, if you're heart so desires. A bright and cheery open dining area is connected to the kitchen - allowing you to chat while preparing meals or snacks. A full bathroom. A utility closet with washer and dryer. Two bedrooms - the master with a queen and television. And the second bedroom boasts a bunk that has a full on the bottom and a twin on the top - how fun is that?! Bring your bikes and ride down to Memorial Park for a little fishing or crabbing. Outside you'll find a cute patio area with sitting area, as well as a small fenced in area that is perfect for your four legged friends to enjoy while you're outside as well. Daisey Cottage is pet-friendly, all members of the family are welcome - book today!

- 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.

Creek House

5 Bedrooms
4 Baths
14 Guests
Mainland
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

Creek House, Privately located in an imaginative setting; nature and history are perfectly coupled with luxurious accommodations.

Rounding the corner of the private country lane, you'll sense something special unfolding before you. What can best be described as an imaginative setting, nature and beauty are perfectly coupled with luxury - a modern 5 bedroom home that's part of a family compound is before you. It sits at the edge of Holdens Creek, where the Pocomoke Sound meets the Chesapeake Bay. You’ve reached Creek House!  Newly renovated and nothing short of spectacular, the WOW factor kicks in as soon as you enter.  Large living spaces with breathtakingly scenic and panoramic water views captivate you. There are Waterside balconies on every level and world class amenities at every turn.  Professional interior finishes bring true elegance to the home’s aesthetic of simple, sexy... and just plain cool. The natural flow from space to space is perfect for a couple to enjoy a romantic getaway or for a large group gathering.  With room for 14 guests, the generous bedrooms offer waterside balconies and marble bathrooms. The kitchen/ dining area can host any size party.

In the garage level of the home, enjoy a game of ping pong on the regulation size table or play a game of cards with the family! Also enjoy the shared use of 2 single kayaks, 1 canoe, and 1 paddleboard.

'Creek House' has partnered with our friends at Sun Outdoors Resort (located less than 2 miles from the house) so that all guests may enjoy the fun resort amenities FREE OF CHARGE. This extra bonus includes a private beach w/ water rentals, pool, playground, "snak shak", comfort stations & more! 

Where is Creek House located? Only a 20 minute drive to Chincoteague Island, Creek House is situated on one of the most beautiful slices of Virginia's Eastern Shore. Day trips to the beach are easy and convenient. Other beach towns like Ocean City, MD and Cape Charles, VA are less than an hour away.  

Creek House has a boat launch, two docks, five porches and a 20’ radius fire pit with outdoor lighting and wi-fi (Bluetooth) speakers system. Simply staying on the property to enjoy a vacation with down time is an option with endless possibilities. The entire compound is available for events and can accommodate up to 18 people (each of the three dwellings are rented separately). Pets will be considered upon request. 

In addition to The Creek House, the compound is also home to two luxurious cottages: Porter’s Barn and Hosta Cottage. Please note that this listing is for Creek House only; the other two cottages - Hosta Cottage and Porter's Barn - must be booked separately. A direct inquiry should be sent for special event pricing or if you wish to rent the entire compound.

GPS is inconsistent on Holden’s Creek Road. Please follow Holden’s Creek Road approximately 1/2 mile and take the first right Drive down the private gravel driveway (labeled: Porterville RD)  past the horse pasture. Take a left at the Y and follow the driveway to the property.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- This property is pet friendly on a case by case basis, with a pet fee per pet. Pet fee is $200 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.

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. 

 

Belle of the Bay

4 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

Truly the "Belle of the Bay", this beautiful custom waterfront home is tucked away at the very tip of one of Chincoteague's most popular residential communities - Oyster Bay I. This means you'll enjoy unobstructed 360 degree water and marshland views from nearly every space in the home. The decor and local art collection alone will "wow" you! Watch the sun rise as you sip your morning coffee from the balcony or screened porch. Enjoy the quiet and privacy as you watch the wildlife that surrounds this fabulous property. The main house features 3 bedrooms, 2 full bathrooms, and an additional loft sleeping area (twin trundle bed). The detached garage features another living area/bedroom (2 Twin beds) that is available for guest use (lower level garage is not accessible by guests). NOTE: Living room fireplace is not functional. 

- 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.

Blissful Oasis

3 Bedrooms
2 Baths
8 Guests
Waterfront
Boat Dock
Gas Grill
Internet

Picture yourself sipping morning coffee on the water's edge, watching herons wade along the shoreline while the Chesapeake Bay stretches endlessly before you. This stunning waterfront rental delivers the kind of coastal living most people only dream about. Tucked away in a beautifully secluded mid-shore location, this three-bedroom, two-bathroom home offers a rare combination of peaceful seclusion and everyday convenience. The star of the show? A long private pier that extends into the bay, practically begging you to launch a kayak, dock your boat, or simply sit at the end with a fishing rod and zero responsibilities.

Inside, the home has been thoughtfully updated to match the magnificence of its surroundings. The renovated kitchen features brand new appliances and a fresh, modern feel that makes meal prep genuinely enjoyable — whether you're cooking up the catch of the day or just reheating leftovers without judgment. Both bathrooms have been completely redone, offering crisp, clean finishes that feel wonderfully indulgent after a long day on the water. The three bedrooms provide comfortable retreats, with the primary bedroom serving as your personal sanctuary overlooking the bay. Natural light pours through the home, connecting every room to the breathtaking waterfront scenery outside.

Despite the gloriously remote feel, practical amenities remain within easy reach. Grocery shopping at Food Lion is a short drive away, and the iconic Chesapeake Bay Bridge-Tunnel provides a scenic connection to the broader Hampton Roads region whenever adventure calls.

This is a home where the rhythm of the tides replaces the noise of daily life. Waterfront rentals like this book quickly - reserve your dates and experience a vacation full of lasting memories!

- 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.

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.

Sunset Bay Villa 118

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Waterfront
Boat Dock
Pool
Internet

Come and sit a spell. Grab a cocktail and watch your worries sail away as you enjoy the cozy private outdoor seating area to be found at Sunset Bay Villa 118. The unit is on the ground level, providing easy access after a long day at the beach. Beautifully styled with nautical decor and special attention to detail. Situated on the edge of the bay, this villa offers a private balcony with walk-out access to the marina and a reserved 40' foot deep-water boat slip. Villa 118 at Sunset Bay boasts an en-suite bedroom with king bed, private bath featuring a stand up shower AND a bathtub - along with private outdoor patio access from the bedroom. Two other bedrooms feature a king in one, and a twin in the other. Fully equipped kitchen and dining area with coffee maker, refrigerator/freezer, dishwasher, electric range, and plenty of countertop for that family seafood feast you will want to make while you're with us. Have a few friends sit at the bar while you mix up a few cocktails, then enjoy "people-watching" on the Chincoteague Channel as the evening picks up. Once the sun goes down you can retire to the cozy living area in the heart of the villa. Maybe a movie on the flat screen? Or perhaps a game of chess? No matter what you decide on, you and your guest will most certainly enjoy your stay at Sunset Bay Villa 118. | Please Note: This unit includes a deep-water boat slip and use of the marina.

- 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.

Avalon

4 Bedrooms
2 Baths & 1 Half
10 Guests
Chincoteague Island
Waterfront
Screened Porch
Internet
Outdoor Shower

Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a large great room that boasts two family rooms, a dining area and large kitchen. From the gas fireplace, to the 16' cathedral knotted pine ceilings, this home is bright, warm and inviting. Avalon offers two queen bedrooms with screened porch access (one private) and two twin bedrooms. Offering over 600 sq. ft. of screened porch - you could live outdoors! The first level also offers a full size futon and 1/2 bath. Avalon is one of our most popular offerings; 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.

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.

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.

Turtle Bay

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Screened Porch
Pool
Internet

Treat yourself to an unforgettable stay at Turtle Bay! This brand new construction will leave you in awe. The coastal décor is everything perfect for a beautiful vacation. Immerse yourself in the plentiful views, sit and sip your morning coffee or evening beverage from the screened porch or cozy up by the fire in the living room. Cooking will be a breeze in the tastefully laid out kitchen featuring stainless steel appliances and granite countertops. Enjoy the large open floor plan and the inviting owners suite with a queen sized bed and  a walk in shower. The other 3 bedrooms also feature queen sized beds, one with a smart tv as well as two full bathrooms.

Turtle Bay is nestled in the beautiful community of Captains Cove Community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. (Fee applies for usage of community amenities.) This rental home is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions).

- 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.

- 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. 

Blue Sea Star

3 Bedrooms
2 Baths & 1 Half
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet

Welcome to Blue Sea Star! You'll fall in love with this fabulous 3 bedroom home from the moment you walk in the door. Bright open spaces, lots of windows, wood floors, first floor master bedroom/bathroom, and too much more to name! Located on a quiet cul-de-sac in the popular Oyster Bay II Community just off of North Main Street. Conveniently located just a few minutes from the downtown waterfront park, shopping, restaurants, movie theater and more! Blue Sea Star features a screened back porch, open side and front porches - perfect for relaxing with a cup of coffee in the morning, or cool drinks after a day at the beach, and a great backyard. As a pet friendly rental, you can even bring your four-legged family member!

- 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.

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