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Grandma's House

4 Bedrooms
3 Baths
12 Guests
Chincoteague Island
Gas Grill
Screened Porch
Internet
Outdoor Shower

Introducing a charming and newly renovated home on Chincoteague Island!  Grandma's House is a delightful residence, boasting four cozy bedrooms, including two primary bedrooms conveniently located on the first floor, each designed for comfort and ease. With three well-appointed bathrooms, including a walk-in shower, the home is designed to cater to your relaxation and convenience needs. Grandma's House also has a handicap ramp for your convenience!

Step into the culinary paradise of a beautifully kitchen, complete with a sleek tiled backsplash, where both seasoned and aspiring chefs can whip up delectable dishes. Connected seamlessly to the dining area, this kitchen is perfect for gatherings and feasts.

Family fun is never in short supply thanks to the inviting den, complete with an air hockey table and darts for a bit of friendly competition. The screened porch offers a breezy retreat for evenings, while the spacious patio is set with both a gas grill and smoker for those sunny weekend barbecues. The heart of this home is undoubtedly its wide-open outdoor space, complete with a basketball hoop for the sports enthusiast and a front deck that invites you to enjoy your coffee while the morning breeze gently brushes against your face.

Whether you're entertaining guests or enjoying a quiet afternoon, this home ensures you can make the most of every moment. So come by and see why this isn't just any house — it's a vibrant living space waiting to be called '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.

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.

Sunset Bay Villa 221

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

Buckle up, folks, because Sunset Bay Villa 221 is here to light up your vacation! This fresh-faced beauty just hit the market and is ready to become your new home away from home. Prepare to be blown away by water views so gorgeous, you'll want to frame them! Every nook and cranny of this place has a view that will leave you breathless.

The open floor plan allows you to cook and entertain at the same time. And let's not forget the deck, the perfect spot to kick back and enjoy your morning cup of coffee or unwind with a glass of wine as the sun sets over the water. The primary bedroom is fit for royalty with a king-size bed to cocoon you in comfort. But wait, there's more! Two additional rooms, one with a king, one with two twin beds, so everyone can sleep tight and dream big. There are tv's in each bedroom as well. Don't miss out on this gem! The Sunset Bay Villa Community has an outdoor pool, indoor workout room, and outdoor dining area!

- 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.

Touch of Grey

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Internet
Outdoor Shower

Welcome to "Touch of Grey," a delightful waterfront rental that blends comfort, style, and convenience into a perfect living space suitable for a variety of lifestyles. This well-appointed house includes three bedrooms, two bathrooms, and a range of updated amenities that ensure a seamless living experience.

Inside, discover a thoughtful layout featuring smart TVs throughout, high-speed WIFI, and a mix of privacy and social spaces that cater to both relaxation and entertainment. The screened porch offers a serene retreat, perfect for enjoying the outdoor air without the bother of pests, and the open deck invites you to bask in the stunning views that surround you.

Step outside to explore the  outdoor space that this property generously offers. A large deck overlooks the tranquil waters, ideal for peaceful mornings or lively evening gatherings. The highlights of the outdoor area include a personal boat dock, which provides immediate water access for boating enthusiasts. Meanwhile, the fire pit setup paves the way for memorable weekend cookouts with friends and family. This home also provides 6 bikes for guest use! 

Pet-friendly provisions mean that your beloved animals are just as welcome as you are, making it a true home for everyone. Functional features are balanced with aesthetic touches to create an inviting environment throughout.

"Touch of Grey" not only promises a picturesque setting but also ensures practicality with its various updates and amenities. Whether you’re drawn to the waterside way of life or simply seeking a tranquil place to call home, this property addresses all facets of modern living. Experience the blend of natural beauty and contemporary comforts in a place ready to be called home.

- 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.

Escape at Deep Hole Hideaway

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

Enter a world of tranquility at Deep Hole Hideaway! Need a break from the daily grind? We've got you covered! Our chic and well-equipped living space will make you feel right at home. And when your tummy rumbles, our kitchen is your culinary sanctuary. Two snug bedrooms await you, furnished with a Queen bed, a Twin daybed, plus a sleeper sofa for your whole posse! The elegant and refreshing décor will overwhelm you with happiness as soon as you step through the front door!

- 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.

Lighthouse View

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water Access
Pet Friendly
Pool
Internet

Lighthouse View is located on the east side of our island and includes a private community pool for your enjoyment. The 3 bedroom, 2 bath townhouse features two first floor bedrooms (one with Roku) with full bath in the hallway and a master bedroom suite upstairs. There's water access across the street with a beautiful waterfront lot and dock. Lighthouse View features wireless internet and cable tv (with a premium tier that includes sports, educational, food and other channels).

- 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. 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.

Modest Junxtion

3 Bedrooms
2 Baths
6 Guests
Cape Charles
Charcoal Grill
Internet

Nestled in the heart of historic Cape Charles, this meticulously renovated family residence stands as a testament to thoughtful design and artistic vision. Originally conceived as a duplex, this home has been masterfully transformed into a spacious single-family haven, where European sophistication meets coastal charm.

The first floor unfolds with an open-concept design, anchored by a gourmet kitchen that would delight any culinary enthusiast. Equipped with premium appliances and an impressive array of cooking accessories, including three distinct coffee-making options, the space beckons both casual cooks and seasoned chefs. The dining area comfortably seats eight, while a cozy coffee nook and music corner, complete with guitars and microphones, add playful touches to the living space. Through elegant French doors, discover an entertainment room featuring a carefully curated vinyl collection for music aficionados.

Ascending to the second floor, two identical queen bedrooms offer serene retreats, while the California king guest room provides a luxurious escape with its distinguished wingback chair and footstool arrangement. A dedicated study space ensures connectivity with fiber optic internet, perfect for remote work or planning your next coastal adventure. The crown jewel of the upper level is the remarkably spacious family bathroom, spanning 250 square feet of pure indulgence.

The outdoor space embraces coastal living with a welcoming front porch, expansive deck, and thoughtful amenities including a fire pit, and grill area. The corner lot location provides ample street parking, accommodating boats and extra vehicles with ease.

This home's proximity to Cape Charles' treasured attractions enhances its appeal, with the historic district and beautiful beachfront just moments away. A decade of careful curation by its overseas owners has infused this residence with a distinctive London-inspired aesthetic, creating an unexpected and delightful fusion of sophisticated urban style and relaxed coastal living.

- 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.

Casa del Mar

5 Bedrooms
4 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Hot Tub
Internet
Outdoor Shower

Casa del Mar - "House by the Sea" - is your home away from home... at the beach! Located in the heart of downtown Chincoteague Island, this grand home has been lovingly maintained and is conveniently situated within walking distance to the waterfront park, boutique shops, restaurants, movie theater and coffee shops! Casa del Mar is one of our newest vacation rental offerings, and we know you'll love it! The spacious, open floor plan features a family room and kitchen, as well as a formal living room and plenty of outdoor space. There's a master bedroom en suite, and the bathroom features a tiled shower and jacuzzi tub. Outside you'll find the perfect backyard, complete with a grill, outside shower. Perfect for relaxing in the evenings after a long day at the beach! And you can even bring the 4-legged family members as well! Don't delay; this one will book quickly! Floor Plan: Downstairs features the living room, family room, kitchen w/ dining area, dining room, master bedroom (King bed & Futon) and full bathroom (shower only). Upstairs features 4 bedrooms - one with a King, one with 2 Queens, one with a Queen, and another with a Queen. The King bedroom and 2 of the Queen bedrooms have attached bathrooms (tub & shower). There is a 3rd upstairs bathroom w/ tub & shower off of the hallway.

- 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.

Trembling Bay

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet

This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. Come and see for yourself; you won't be disappointed!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pet Friendly with a fee, No cats, 2 dogs max. ($150 per pet) 

- 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.

Diving Duck

5 Bedrooms
2 Baths & 1 Half
10 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Hot Tub
Internet
Outdoor Shower

If you're looking for the complete vacation package, look no further! This 5 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room with access to the waterside deck, a large dining area, kitchen with all the counter space you'd ever need, a half bathroom, and the master bedroom with private bath (with custom tile shower and soaking tub). Upstairs features a landing area with sofa and foosball table, 4 more bedrooms and another full bathroom. Aptly named, 'Diving Duck' is the perfect spot for watching the ducks and wildlife pitch in the bay just out the back door. There's even a floating dock perfect for launching canoes and kayaks! And as if all of that is not enough, the 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). What more could you ask for? Book your stay at 'Diving Duck' today! Additional game room with wet bar and pool table, and a private hot tub. All of this in addition to interior updates and renovations!

- 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.

- Community amenities require passes for an additional fee. Although the rental home can accommodate up to 10 guests, only 8 guests are permitted to use the community amenities (pool, etc.) at a time.

- 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 Moon

4 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet

Come and enjoy a nice, relaxing vacation at this charming island home. "Blue Moon" is centrally located on Chincoteague Island - it's not too far from downtown, a public boat launch, nature trails, and one of the island's most-loved fresh seafood shops! Downstairs features the living room/dining area combo, a lovely kitchen, full bathroom and 2 screened porches. On the second level you'll find 3 bedrooms and another full bathroom. The third level is the master bedroom suite with a King bed and full bathroom. If you enjoy the more traditional-style homes, "Blue Moon" might be the one for you!

- 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.

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.

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