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Island Sunrise

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

Island Sunrise is a gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly, but it offers a deep water boat dock and 3 spacious decks. Aptly named, the sunrises and views of Assateague Island and the Assateague Channel truly are second to none! If you're looking for a nice, relaxing vacation home to enjoy your vacation, look no further. Island Sunrise is it!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with an additional fee of $200 per pet. All pets must be disclosed prior to arrival. Pet restriction: limited to two 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.

Oyster Catcher

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet

Welcome to Oyster Catcher! This home offers a prime location, beautiful views and a deep water dock (6 feet at low tide)!  We encourage you to sit and relax on the large screened porch and enjoy all nature has to offer. Upon entering the home from the side door, you'll be greeted by the the fully equipped kitchen that provides all the essentials for meals at home, while overlooking some of the most beautiful views the Island has to offer. The living room does not lack views either- sit and relax while opening one, or all four, of the large panoramic folding doors that span across the kitchen and living area. Enjoy the sounds of nature or feel the cool salt air breeze. There is a first floor bedroom, with a full size bed and a separate full bath (tub/shower combo) - you have your own access to the screened porch from the first floor room.  The living room also has a queen sleep sofa.  Upstairs you will find two more bedrooms, one with two twins and another with a full. All bedrooms showcase breathtaking views of Deep Creek. Venture outside to the private guest cottage that holds much history from one of the Islands most plentiful seafood shacks. The guest cottage features a queen bed and full bathroom with shower, as well as a floating twin bed. Drop a line or a crab pot at the end of your private dock- maybe you will even get to enjoy a fresh catch for dinner! Oyster Catcher offers a private setting with bountiful plants and greenery, plenty of yard for whole family including your fur babies!  Other amenities include a gas grill and WIFI.

- 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.

 

Coastal Cottage

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in the popular Oyster Bay II community is where you'll find our newest vacation home addition - ' Coastal Cottage'! Completely remodeled and adorned with simple, beachy-chic decor, you'll enjoy a most comfortable stay at this lovely home. The open floor plan features a main living room area, sitting area, dining room and large kitchen space with breakfast bar/center island. All of the bedrooms and both full bathrooms are on one level making it convenient for single-level living. The master bedroom with en suite bath has a queen bed, the second bedroom has a queen bed, and the third (large) bedroom has 2 queen beds side-by-side. Come for a stay at 'Coastal Cottage' - it may just become your next favorite beach home!

- 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.

Dragonfly Point

4 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

"DRAGONFLY POINT" is a magnificent waterfront property on Oyster Bay & canal. Surrounded by water on three sides of the home, you see the bay and canals from every window! The abundance of decking for entertaining will amaze you with easy access on both floors. Upper family room/loft with unobstructed views. The home has beachy-chic feel with built in bookcases, shiplap, custom fixtures and bathrooms, and more. Two master bedroom suites - upper and lower. Totally fenced in yard that has mature plantings, kayak launch with concrete pad, 120' pier that extends into the bay, comfortable screened porch and much more! Many updates recently including washer & dryer, brand new kitchen & appliances, new bathrooms, etc. SIMPLY BREATH TAKING VIEWS! Come for a stay at Dragonfly Point - it's one you surely will not forget!

- This property has a 7 night minimum stay year 'round. 

- 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.

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.

June's Retreat

4 Bedrooms
5 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

June's Retreat is Chincoteague Island's premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms with floor-to-ceiling windows to the expansive wrap-around verandas, you'll feel as though you're one with nature and your surroundings. Downstairs features a chef's quality kitchen, private billiards room, waterside glass atrium, living room, private den, formal dining room, sitting room and a bathroom. Upstairs you'll find 4 bedrooms with bathrooms (en suite), a sitting area and balcony. The panoramic views of Chincoteague Bay are unobstructed and unsurpassed. Come and see for yourself; we promise 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.

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.

Crabby Pines

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

Discover comfortable vacation living in this charming one-level ranch home. "Crabby Pines" offers a cozy retreat with three bedrooms and two bathrooms, providing ample room for relaxation and privacy. The house is ideally situated in a serene residential neighborhood and features modern amenities that ensure a seamless, convenient lifestyle.

Enjoy the convenience of being just minutes away from the public boat ramp at Fur Landing. Outdoor enthusiasts will appreciate the close proximity to nature trails and a dog park, perfect for morning jogs or leisurely evening walks with your furry friends. Oh, did we mention this home is pet friendly? Additionally, the property is located near the 'Beach Road,' a vibrant area bustling with mini-golf, dining options, ice cream shops, and boutiques - offering endless entertainment options.

This welcoming home is designed with practicality in mind, ensuring that each space is utilized efficiently while still exuding a sense of warmth and comfort. The property's easy access to local amenities, combined with its peaceful surroundings, makes it an ideal choice for anyone looking for a balance between nature and community activities.

Whether you're settling down with family or looking for a tranquil spot to return to after a day of adventures on the island, this home is sure to meet your needs. Embrace a laid-back lifestyle in Chincoteague with this delightful vacation home opportunity.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This home is pet friendly with an additional fee. Maximum of two dogs under 25 lbs. each; no cats. 

- 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.

Serenity at Deep Hole Hideaway

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

Welcome to your blissful oasis, "Serenity at Deep Hole Hideaway!" This charming haven has been given a complete makeover to cater to all your vacation dreams. The kitchen is stacked with top-notch gadgets to whip up that perfect meal. The living room features a cozy sleeper sofa to squeeze in a few extra guests. The main bedroom boasts a luxurious queen-sized bed, while the guest room offers a snug twin daybed, providing ample space for up to six guests. Step outside and relax on the deck, indulging in a long-awaited book. And, if you're in the mood for some classic campfire fun, gather around the firepit and toast up some scrumptious S'mores and hotdogs!

- 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.

Hidden Treasure

4 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

"X" marks the spot here at Hidden Treasure. Nestled in a cove along the shoreline of the island's most exclusive neighborhood on the northern end, you'll have everything you need for a perfect family vacation. ENDLESS outdoor space in the form of a long private dock with a large sitting area at the end, huge deck off the living area overlooking the water, a screened in dining area off the deck, and a large shared balcony off of two of the bedrooms on the upper level. The spacious home offers 4 bedrooms and 3 bathrooms. On the ground level you'll find the fully-equipped kitchen with breakfast bar and dining area. The kitchen opens up to the cozy living area, with a fireplace and an unbelievable view of Chincoteague Bay. You'll find plenty of seating for your family, just around the corner is another sitting area for overflow - or if you just want to curl up with a good book alone (no judgement!). Also located on the ground level is a full bath and bedroom with two twins - ideal for putting the little ones to bed but still being able to keep an eye on them. Upstairs you'll find the other 3 bedrooms. The master suite - furnished with a king bed, bath with Jacuzzi soaking tub and shower, flat-screen, and yet another knockout view on the balcony. The balcony runs the length of the house and is shared on the other end with a bedroom with a queen. An additional full bath, and another bedroom with two twins is also found upstairs as well. Crab and fish right off the dock, and enjoy cooking and enjoying your bounty together al-fresco at the screened-in porch on the deck. Or pour yourself a nice chilled beverage and walk down to the end of the dock and wait for the sun to slip under the horizon over Chincoteague Bay - bringing the end to another day of treasured memories made at Hidden Treasure.

- *NEW FOR 2025: Level 2 EV charger!*

- 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.

Beachin' at the Cove

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Pool

Come and enjoy a private place to call home during your much needed vacation! Beachin' at the Cove has everything you need to enjoy a quick or extended getaway.  The location of this inviting home is superb! Overlooking one of the Shore's best golf courses, Beachin' at the Cove provides a desired location for your perfect beach escape. In this cozy, single family home, you will be greeted by a covered porch where you can sit and sip your morning coffee or tea. You will then enter an inviting, open living area adjacent to the kitchen with access to the large and open back deck. This home offers first floor sleeping quarters as well as a full bathroom and hardwood flooring throughout. Upstairs you will find 2 more bedrooms and another full bath. The beautiful community of Captain's Cove offers many amenities, with something suited for the entire family. Beachin' at the Cove is located just a short distance from waterfront dining on the Chincoteague Bay, 3 pools, a 9 hole golf course, tennis, basketball, fitness, and much more! Conveniently located, you're approximately 20 minutes from Chincoteague Island, 30 minutes from Snow Hill and less than an hour to Ocean City MD.

- 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. No Sunday check-ins or check-outs are permitted. 

Bayside

3 Bedrooms
2 Baths
8 Guests
Cape Charles
Town & Country
Pet Friendly
Gas Grill
Internet

Welcome to Bayside, your next relaxation haven! This charming 3-bedroom, 2-bathroom duplex offers the perfect blend of comfort and convenience nestled in the delightful town of Cape Charles. Whether you're in town to soak up the sun at the beach or simply unwind, this property is designed to suit every aspect of your leisurely needs!

Step inside to discover a cozy atmosphere with well-appointed spaces that promise a homely feel from the moment you walk in. The primary bedroom, a restful retreat, along with two additional amply-sized bedrooms, ensures everyone has their personal space. Entertaining? The open-concept living area present the ideal setting for creating memories with loved ones.

Forget about the hassle of street parking; this house comes with its very own off-street parking spots. And for those who can't bear to leave their furry friends behind, you'll be pleased to know this home is pet friendly!

Just a short stroll away lies Central Park, where you can enjoy everything from a peaceful morning jog to a lively afternoon picnic. Need to pick up some essentials or a quick snack? There are many conveniences in town, or the grocery store is just a little over 2 miles away—talk about convenient shopping!

Whether you're looking for a calming weekend getaway or seeking a serene place to call home for a while, this house ticks all the boxes for a laid-back yet vibrant living experience. Book your stay, pack your bags, and prepare to relax—your beachside vacation awaits!

Located right next door to this beautiful duplex is "Seaside". Larger group? Bring along your friends and family and rent both units! 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation. 

- This property is pet friendly for an additional fee (NO CATS). The 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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