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Donovan's Reef

3 Bedrooms
2 Baths
8 Guests
In Town
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 not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Chamallow

3 Bedrooms
2 Baths & 1 Half
12 Guests
North Main
Waterfront
Pet Friendly
Gas Grill
Internet

Look at this beautiful, newly renovated home in the sought-out community of Richardson's Landing. This home is conveniently located right on the water and offers a wonderous, relaxing view. You will not be disappointed with any aspect of this gorgeous home... upon entering you will be swept away with all of the beautiful upgrades this charming Cape Cod has to offer. Chamallow features 3 bedrooms, a bonus kids loft above the garage, sunroom, two dens (one of which features a kitchenette), a brand new deck, fire pit, new floating dock, brand new kitchen, upgraded bathrooms, and so much more. Enjoy the large yard that has plentiful room for the kids to run, and bring your fur babies too! 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Admiral Benbow

3 Bedrooms
2 Baths & 1 Half
8 Guests
Oyster Bay
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 not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Olive Ponies

2 Bedrooms
1 Bath
9 Guests
East Side
Water View
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to Olive Ponies! This charming house offers a serene living experience with picturesque water views that promise to elevate your everyday life! (Please note: rental includes the upper level only; lower level is not accessible by guests.)

Nestled in a peaceful neighborhood, this property boasts two well-appointed bedrooms plus two additional sleeping areas, each featuring convenient luggage racks for easy organization. The single bathroom is thoughtfully designed to accommodate the needs of a household. This home provides a cozy yet comfortable living space suitable for everyone.

The heart of this residence is its outdoor deck/balcony, where you can enjoy breathtaking views and fresh air, making it the perfect spot for relaxation or hosting gatherings with loved ones. Additionally, the proximity to Memorial Park offers endless opportunities for outdoor activities and leisurely strolls in nature, ensuring you have both tranquility and recreation right at your doorstep. On the first floor, you have access to a screened porch for those buggy evenings. 

Parking is a breeze with three dedicated spaces available, ensuring convenience for you and your guests. 

Whether you're savoring the water views from your deck or exploring the nearby park, Olive Ponies offers a unique blend of comfort, convenience, and natural beauty. Don't miss out on making this house your new vacation spot, where every day feels like a retreat.

- This rental home is located on the upper level (lower level is private living space and not accessible by guests).

- No smoking is permitted on the premises. 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No pets.

- 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.

Off Belay

4 Bedrooms
3 Baths
8 Guests
North Main
Water View
Gas Grill
Screened Porch
Internet

Welcome! This spacious, luxurious home offers everything you need for a relaxing vacation. Located in the Smugglers Cove community, Off Belay is situated on a small creek, perfect for any nature enthusiast. Upon entering this gorgeous vacation home, you will be enamored with the thoughtful décor and tasteful furnishings. Beautiful hardwood floors lead you to the gourmet kitchen with an expansive kitchen island, including a 5 burner gas range. The living room boasts high ceilings,  plenty of seating,  a wood burning fireplace, and tv as well as access to the large screened in porch and open deck. The first floor also offers a primary queen suite with an attached bath (shower only), and a private den with tv and a queen sleeper sofa. You will also find another full bathroom, washer/dryer and utility sink just down the hall. Upstairs, there are two more bedrooms: a king room with a jack and jill bath as well as a twin room. Walk out to the large deck from the second floor and take in all the views Off Belay has to offer! There is plenty of out door space for entertaining, sitting and relaxation. You also have use of kayaks and a canoe. (pictured) 

- SPECIAL NOTE: This rental home has a 7 night minimum year 'round. 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Blue Crab Bungalow

2 Bedrooms
1 Bath
5 Guests
In Town
Gas Grill
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 2 bedrooms 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 bedroom serves  as both a bedroom 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 not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Sea Oats

3 Bedrooms
2 Baths
8 Guests
Oyster Bay
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

A destination unto itself, Sea Oats offers wide open spaces, beautiful waterfront and views of Oyster Bay and plenty of room to spread out and relax. A luxury vacation rental home with all the bells and whistles, Sea Oats will delight your senses. From the tastefully decorated rooms and high-quality furnishings, you'll enjoy a great vacation without skimping on anything! Relax on the waterside screened porch, the sun deck or the ground-level covered porch after a great day at the beach. Or enjoy the hammock -- it's located in a nice shady spot -- as well as crabbing/fishing right from the dock! Clean your catch of the day at the fish cleaning station, then cook it on the gas grill. Bring your boat or kayak and dock it! Accommodations for 8 include a master bedroom suite with queen bed, 2nd bedroom with another queen bed, 3rd bedroom with two sets of bunks (2T on one side and T/D on other side), and a queen sleeper sofa in the living room. 2 full baths, a large outdoor shower and a very well-equipped kitchen with laundry will meet your every need.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

The Virginian

4 Bedrooms
2 Baths & 1 Half
13 Guests
North Main
Waterfront
Gas Grill
Internet
Outdoor Shower

Welcome to The Virginian, a stunning waterfront residence. This spacious property, boasting 2,296 square feet of living space, offers a serene and picturesque setting that's sure to captivate.

Step inside to discover four generously sized bedrooms, all  located on the second level, providing a private and tranquil retreat for relaxation. The home features 2.5 bathrooms, with a half bath located downstairs.

The heart of this home is its open and inviting living areas, where beautiful views of the waterfront can be enjoyed. These views set the perfect backdrop for both everyday living and entertaining.

Outside, the property continues to impress with its thoughtful amenities designed to enhance your living experience. An outdoor shower provides a refreshing option on warm days, while a propane grill awaits for those delightful gatherings with friends and family. The residence is also accompanied by four parking spaces, accommodating vehicles comfortably.

Recent improvements throughout the home ensure a contemporary and comfortable lifestyle, allowing you to move in and enjoy from day one.

Situated in a peaceful location, this house not only offers stunning views but also provides an ideal setting for those seeking a blend of tranquility and convenience. Whether it's waking up to the gentle sounds of water or hosting memorable get-togethers in a beautiful setting, The Virginian presents an exceptional renting opportunity..

This home features tons of new upgrades for the 2024 season! The Virginian features new paint, bedding, updated furnishings, artwork, new mattresses, curtains and 3 new smart tv's!  Downstairs you'll find a large living/dining room combo and a nice modern kitchen. Off the kitchen is a private den area with a new twin sleeper- a perfect spot to catch up on your reading! There's a half bath on the first floor. All bedrooms are on the second level. There's a owner suite, with a king bed as well as another full bath on the second level. You will also find another bedroom, featuring a new king bed, as well as the 3rd bedroom featuring a queen sized bed. The 4 bedroom is the bonus room- this room is complete with a new full bed and 4 twin beds. The Virginian features central heat and air, laundry facilities, garage, propane grill, outdoor shower, and more! Located on a bulkheaded lot on a canal that comes up from Oyster Bay, you can throw your crab pot in right outside the back door.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

A 'Teague of Our Own

3 Bedrooms
1 Baths & 1 Half
8 Guests
In Town
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to A 'Teague of Our Own! This in-town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated in 'beachy-chic' decor! The living room has abundant seating, complete with a flat screen TV and electric fireplace for those off-season stays. The kitchen is stocked to a chef's standards - there's nothing you won't find including a gas stove, sharp knifes and an herb garden. You will also find a queen sized sleeper sofa in the living room. The three bedrooms are upstairs, and the full bathroom (tub and shower) is downstairs. The enclosed porch with sliding windows allow for room to spread out in any weather. Large carport to keep a vehicle and all your gear under cover. A huge yard for cookouts, games and showering in the outdoor Tiki-shower. This fabulous vacation home truly has it all and has become one of our most popular rental homes. Don't delay; book today! 

- No smoking is permitted on the premises. 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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: limited to one small dog only.

- 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.

Paradise View

4 Bedrooms
4 Baths
10 Guests
North Main
Waterfront
Boat Dock
Gas Grill
Internet
Outdoor Shower

Truly a masterpiece, this luxury vacation rental home offers only the finest amenities. Each bedroom is a separate suite with private bath. The master bedroom suite (K) features two a spa bath with jetted tub, a private waterside deck area and beautiful water views. To capture the best views, you'll find 3 bedrooms (K,Q,2T) and a private reading room with writing desk on the first floor. The second floor features a spacious and lovely great room with water views in all directions. To aptly describe it, there's room for everyone. There's a chef's kitchen with center island, a large dining area, a large living room area with multiple sofas, tv, fireplace and deck access. There's a game area with Foosball table and a small waterside sun room area off the dining room. There's a wonderful separate lounging room, complete with wet bar, that creates a luxurious space for private affairs. In addition, there is a master bedroom suite on the second level with tv and private bath (with shower). The home is situated on a waterfront lot overlooking Oyster Bay. You'll enjoy breathtaking sunrises/moonrises. You can dip your fishing pole in the water or throw the crab trap over and catch your dinner. Paradise View is a beautiful home and you'll enjoy making vacation memories here. It's a place you'll want to return to time and time again.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Blue Sea Star

3 Bedrooms
2 Baths & 1 Half
12 Guests
North Main
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 not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Charlie's Bayside Retreat

3 Bedrooms
2 Baths & 1 Half
8 Guests
South Main
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 not included with your reservation. Please inquire about our new attractive linen packages!

- 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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