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Cockleshell Cottage

3 Bedrooms
3 Baths
10 Guests
Oyster Bay
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage! This modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs features 2 more bedrooms (Double and Double/pull-out Twin trundle), and a full bathroom. Cockleshell Cottage is handicap accessible. Relax and enjoy the breeze on the open front porch or back screened porch. Call us today; this home books fast!

- 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. Pet restriction: limited to two small dogs 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.

Daisey Cottage

2 Bedrooms
1 Bath
7 Guests
South Ridge
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, to Etta's Channelside for a nice dinner out, or Ridge Road Pit Stop for a quick bite to eat. 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.

Anchors Away

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Pet Friendly
Gas Grill
Pool
Internet
Outdoor Shower

Welcome to "Anchors Away," a captivating waterfront home now available for rent, offering an unparalleled living experience. This remarkable property boasts four generously sized bedrooms and three well-appointed bathrooms, providing ample space for comfort and privacy.

Nestled in a vibrant community known for its welcoming atmosphere and scenic beauty, this home is designed to impress with its stunning waterfront views that can be enjoyed from the spacious decks - perfect for entertaining or simply unwinding in nature's embrace.

The first-floor suite offers convenience and accessibility, ensuring that everyone can enjoy this home's charm without compromise. The interior is just as impressive, featuring granite countertops and stainless appliances that add a touch of elegance to the functional and stylish kitchen. 

With parking space for up to four vehicles, you'll find this property not only beautiful but also practical. The pet-friendly policy ensures that your beloved companions can join you in calling "Anchor's Away" home.

This house is more than just a place to vacation; it's an opportunity to make life-long memories for those who value beauty, community, and comfort. Whether you're gazing at the serene waters from your deck or enjoying the modern amenities inside, this home invites you to live your best life.

Don't miss the opportunity to make "Anchor's Away" your new haven. Contact us today to experience firsthand everything this exceptional rental property has to offer.

- 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. Pet restriction: 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.

- 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. 

Windshadow

3 Bedrooms
2 Baths & 1 Half
8 Guests
North Main
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining area. Walk through the french doors off the living room to a large screened porch and sky deck overlooking the Chincoteague Bay. There is a first floor King bedroom with en-suite bath and two twin bedrooms on the second level. Windshadow is a premier PET FRIENDLY vacation rental.

- 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.

Wildcat Retreat

4 Bedrooms
4 Baths & 1 Half
10 Guests
North Main
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Only for the discerning traveler, 'Wildcat Retreat' is the newest in luxury vacation accommodations on Chincoteague Island. The reverse floor plan is over 2,800 square feet and offers views of the bay and marshlands where wildlife abounds from nearly every room. The first floor features 4 bedrooms, all en suite with full bathrooms and a large recreational room with second kitchen and waterside deck. The second floor features the main living areas - living room, dining room, kitchen, powder room - as well as another waterside deck and screened porch. If you enjoy fishing and crabbing, or just sitting at the water's edge, you'll LOVE the 500' private pier that extends into the Chincoteague Bay! Vacationing with a large group? Check out the sister house 'Wildcat Haven' right next 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. 

- Pet friendly with 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.

Tall Pines

2 Bedrooms
1 Baths & 1 Half
6 Guests
Piney 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 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.

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 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.

Pony View

3 Bedrooms
3 Baths & 1 Half
8 Guests
East Side
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Internet

Enjoy your cup of coffee as the sun peeks over the salt marshes of Assateague Island. You can often see a herd of our famous wild ponies grazing to the right of the lighthouse from your private waterfront deck and second-floor balcony - not to mention the copious amounts of waterfowl and other wildlife in the channel. Pony View boasts three bedrooms - A master with queen bed, full bath, and balcony on second floor, as well as another bedroom with a queen on the second floor - along with another full size bath. On the third floor you will find an amazing view of the marsh with the panoramic window and four twin beds, and a beautiful bathroom with a rustic wooden sliding door. The ground floor is where you'll find the hub of the house - fully equipped kitchen with refrigerator, electric range, dishwasher, and plenty of counter space. A dining table and bar seating area, a half bath, and a cozy living area with floor-to-ceiling knockout views. Or enjoy the waterfront deck just outside the living room. Pony View is pet-friendly so your furry friend can enjoy the water view as well. Dock access along with a boat slip is available for your use. Crab and fish right from the house! A deep water boat ramp is found just at the end of the complex for you to drop in. Central air/heat will keep you comfortable year round. There is also a washer/dryer, and an outside grill for your use while you're with us. Memorial Park is just a short walk up the street for a wonderful waterfront park and playground, tennis and volleyball courts, fishing pier, picnic areas, and walking trail.

- 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.

Sea Glass Retreat

4 Bedrooms
2 Baths & 1 Half
8 Guests
Captain's Cove
Town & Country
Pet Friendly
Screened Porch
Pool
Internet

Welcome to the beautiful, BRAND NEW 'Sea Glass Retreat'! Located in the ever-popular Captain's Cove community on a quiet wooded cul-de-sac, this 4 bedroom home features all new amenities and is waiting for you! Enjoy the serene setting and watching wildlife from the private screened porch, take a walk through the community, or just relax indoors on the new, comfortable furnishings. This home is conveniently located to all the community amenities such as pools (2 outdoor & 1 indoor), fitness center, marina w/ fishing pier, restaurant, tiki bar, and more! If day-tripping is more your style, you'll love the fact that this home is located only 20 minutes from Chincoteague Island and the beach, or 30 minutes to Ocean City, MD and the boardwalk amusements. Either way, a fabulous vacation is calling your name at 'Sea Glass Retreat'!

- 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: 2 pet max.

- 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. 

Southern Breezes Nor' Easter

3 Bedrooms
1 Baths & 1 Half
9 Guests
Cape Charles
Pet Friendly
Internet
Outdoor Shower

Welcome to Southern Breezes Nor'Easter, Unit 104B – your next vacation home that combines comfort, convenience, and the joy of beachside living! This inviting duplex is now available for rent and offers a perfect blend of space and functionality to cater to a variety of living arrangements.

This home features three cozy bedrooms and 1.5 bathrooms, ensuring ample space for up to 9 occupants. Whether you're looking to create memorable moments with family or share a comfortable living space with friends, this property is designed to accommodate your lifestyle.

The ground floor hosts plenty of space and promises delightful meals and gatherings. The kitchen is equipped with essential appliances and ample storage, making meal preparation both enjoyable and efficient. There is even an ice cream maker to enjoy on those warm days! The living area extends onto a covered front porch, offering a serene spot to relax and enjoy the gentle coastal breezes.

Located within one block to the beach, this property positions you perfectly to enjoy sandy shores and spectacular sunsets whenever the mood strikes. Its great location also means you're never far from local amenities, including shops, restaurants, and entertainment options.

Southern Breezes Nor'Easter is more than just a place to live; it's a lifestyle choice for those who value convenience, community, and the allure of coastal living. Discover the joy of making this duplex your new relaxation spot and embrace a life where every day feels like a vacation! 

Located right next door to this beautiful duplex is Southern Breezes Nor'Wester. 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 with a pet fee per pet (no cats). 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.

Twins at Bay

3 Bedrooms
2 Baths & 1 Half
8 Guests
Cape Charles
Pet Friendly
Gas Grill
Internet

Welcome to your next coastal retreat at "Twins at Bay"! This charming 3-bedroom, 2.5-bathroom house offers the perfect blend of historical allure and modern convenience. Each bedroom, situated upstairs, promises peaceful private spaces, while the welcoming front porch invites you to enjoy serene evenings or lively mornings with the convenience of the downtown area. 

Imagine stepping out to bask in the aroma of saltwater only a few short minutes away,  and spending your days exploring local attractions. Perfect for seafood enthusiasts, the area boasts some of the best dining spots where you can indulge in fresh catches daily. If you're feeling sporty, challenge your friends or family to a playful round of miniature golf nearby. For those days when you'd rather stay close to home, the property comes complete with a gas grill—ideal for those impromptu barbecues. The beach is just a heartbeat away, offering endless sand, surf, and sun for all who crave the ocean breeze.

Pet lovers rejoice! This home embraces your furry friends, making it a true family haven. The friendly neighborhood further adds to the vibrant community spirit, ensuring every occupant feels instantly part of the local fabric. Twins at Bay is newly renovated and perfect for your next vacation! 

- 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 (no cats). 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.

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 pet friendly 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 with a pet fee per pet (no cats). 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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