Vacation Rental Homes

We're pleased to be able to offer 'High Tide' as one of our most popular vacation rental selections! The true epitome of a beach house, you'll enjoy the bright, cheery decor and spacious feel of this fabulous home. The downstairs features an open living room (with fireplace and flat-screen TV), dining area and kitchen, as well as over-sized windows and access to the two (yes, TWO!) screened porches. One porch features a wonderful dining set; perfect for dining al fresco. The second spacious porch features a large hammock and nice sectional lounging sofa. As if that's not enough outdoor space, there are also multi-level, open air decks on the front and back of the home! There's also a bedroom (king) and full bathroom downstairs. The upstairs features two additional bedrooms (one with a queen & two twin beds, and the other with a queen & one twin bed), and a full bathroom. Both upstairs bedrooms are enhanced by sliding doors and private balconies. You'll enjoy snippet water views of the Assateague Channel! Don't delay, 'High Tide' books quickly. Please note: As part of the Piney Island Community, this rental includes water access at a shared community location just a short distance from the 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.

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.

New to the rental market, "Play By The Bay" is a brand-new 3-bedroom, 2.5-bath house designed for easy coastal living in Cape Charles—where your biggest daily decision is beach time or backyard time.

Step inside to fresh finishes and a bright, open layout that keeps everyone connected, from morning pancake duty to game night. The upgraded chef’s kitchen is the star of the show, with plenty of workspace for slicing, sautéing, and showing off your “I totally meant to do that” plating skills. The main living area flows naturally for lounging, streaming, and post-sunshine naps.

The primary en suite offers a calm retreat, while two additional bedrooms provide flexible space for guests, kids, or that quiet workspace that you may need on occasion. With two full baths plus a convenient half bath, morning routines stay conveniently civilized.

Outside, enjoy a large yard set up for fun—bring your competitive spirit for lawn games or simply claim a chair and supervise like a professional. Bicycles are included, because Cape Charles is better at a relaxed pace and parking worries are not invited.

You’re close to historic downtown Cape Charles for shops, dining, and strolling, and the beachfront is an easy ride away when the water starts calling your name. Groceries are nearby too, so ice cream runs can remain an important part of your schedule.

Ready to make this coastal getaway your 'home away from home'? Book today and start your annual vacation tradition!

- 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.

Spend your precious vacation time at this truly stunning, one-of-a-kind architectural masterpiece! From the moment you walk in the French entry doors, you'll be "wowed" by the floor to ceiling windows and 3-sided glass fireplace. The chef's quality kitchen is brand new with stainless steel appliances and granite counter tops. There are multiple decks for enjoying some relaxing downtime and taking in the unobstructed views of Oyster Bay. Professionally decorated with clean, modern Bohemian-chic decor and furnishings, you'll find yourself surrounded by simple, upscale comfort. There's a 70" TV in the living room, and all the bedrooms feature their own flat-screen TVs and Amazon Echo devices. Stream all of your favorite shows from Hulu, Netflix or Disney+! "Sunrise Shore" is located in one of Chincoteague Island's most popular waterfront residential communities - Oyster Bay I. Conveniently located to Maddox Blvd. (Beach Road) and downtown Chincoteague, yet far enough to escape the hustle & bustle. | | The main level of this home features the main living areas (kitchen, dining room, living room), a powder room, a pool shower bathroom ,and the master bathroom en suite. The upstairs features 2 more bedrooms, both with private balconies, and a full bathroom. There's also an additional loft sleeping area. | | The outdoor areas offer exceptional entertaining and relaxation space. Cool off in the 10' x 40' saltwater in-ground pool, or gaze at the stars as you spend the evening in the 6-person hot tub. Dine al fresco on one of the many decks, all while enjoying the water views. There's plenty of room in the yard for a game of corn hole or catch.

- 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.

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.