Vacation Rental Homes

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.

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.

Check out Chincoteague’s newest Piney Island vacation rental! Hailey’s Round House is in a prime location on Chincoteague, in a quiet development road but just a short walk to the bridge to Assateague and the Maddox Boulevard shops and restaurants!  You could take a bicycle or short drive to the Assateague beach and access to all of the bicycle trails around Chincoteague and Assateague to enjoy the wild ponies or many of the restaurants on Chincoteague.   

Hailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed.  You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay! 

- 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.

Discover this exceptional new construction home nestled within the prestigious Bay Creek community, where luxury living meets coastal charm. This stunning six-bedroom, five-bathroom residence showcases meticulous attention to detail and uncompromising quality throughout every square foot.

The welcoming front porch overlooks beautifully landscaped grounds, creating an inviting first impression that sets the tone for the extraordinary experience within. Step inside to find spacious rooms designed for both comfort and elegance, with an open great room featuring a cozy fireplace that seamlessly flows into the formal dining area and chef's dream kitchen. Custom large doors provide effortless access to the back porch, perfect for alfresco dining and entertaining under the coastal sky.

Every bathroom represents a spa-like retreat, featuring luxurious soaking tubs and sophisticated tile and glass showers that transform daily routines into rejuvenating experiences. The primary bedroom, and additional bedrooms alike, offer generous proportions and thoughtful design elements that ensure comfort for both family and guests.

The indoor and outdoor spaces transition seamlessly and continue the home's commitment to exceptional living, with a dedicated kids' play area, multiple sitting areas for quiet contemplation, and a relaxing hot tub for ultimate unwinding. As if that's not enough, the spacious garage hosts a fabulous entertainment room with leather reclining chairs, a large TV, pool table and shuffleboard. Above the garage has been designed as a private 'in-law' suite, featuring a kitchenette, bedroom, bathroom and sitting area. Two custom, 6-seater golf carts are available for convenient transportation throughout the community complete the ultimate experience (additional fee of $200 per day required).

Bay Creek community membership provides access to world-class amenities that rival the finest resorts. Residents enjoy the renowned golf course designed by championship standards, scenic nature trails winding through pristine landscapes, refreshing community pools, a comprehensive fitness and life center, and exclusive access to a private beach along the Chesapeake Bay.

The location offers the perfect balance of tranquil coastal living and convenient access to regional attractions, including proximity to the Cape Charles Beachfront and the engineering marvel of the Chesapeake Bay Bridge-Tunnel. 

From top to bottom, no detail has been overlooked in creating this masterpiece of modern coastal living. The combination of superior construction quality, premium amenities, and an enviable location within one of Coastal Virginia's most sought-after communities makes this rental opportunity truly extraordinary for discerning tenants who appreciate the finest things in life.

Please note:

- Two custom, 6-seater golf carts are available for convenient transportation throughout the community complete the ultimate experience (additional fee of $200 per day required).

- 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.

- Usage of the Bay Creek Resort amenities requires an additional fee of $75 per day*.

BAY CREEK RESORT AMENITIES:

Waterfront area perfect for kayaks, canoe, fishing or crabbing.

27 hole World-class golf course (requires additional golf fee).

Golf lessons and clinics available for all skill levels.

Member lounge with billiards and entertainment.

Cardio and weight training studio.

Two outdoor pools w/ decks and furniture.

350 acre Nature Preserve w/ trails and wildlife viewing.

Clubhouse with private restaurant and dining experiences.

Structured activities and programs such as bird watching, paddle-boarding, beach yoga, kid's camps & more. 

*Fee is subject to change without prior notice or authorization. Bay Creek Amenity offerings can be seasonal and may change without prior notice or authorization.

Cute, clean, and chic — this cozy one-bedroom, one-bathroom studio apartment has everything you need for easy island living on Chincoteague. Whether you're looking for a seasonal escape or a place to call your home away from home, this little gem delivers big on charm without the fuss.

Step inside to find a full kitchen ready for your culinary adventures — from simple morning coffee to a full-blown seafood feast after a day at the beach. Full laundry is conveniently right on-site. It's the kind of place where you can kick off your sandals and just breathe.

Conveniently located near the carnival grounds and South Main Street, you're never far from the heart of island life. Veteran's Memorial Park is just a short stroll away for those peaceful morning walks. Need groceries? Island Foods Great Valu is right up the road. Feeling adventurous? Maui Jack's Waterpark and the stunning Assateague Beach are both within easy reach for endless fun in the sun.

Here's a fun bonus — this apartment is attached to a charming property affectionately known as "Grandma's House," which is available as a separate rental. Rent them together for a larger group or keep things simple and snag just this spot for yourself.

Island living doesn't have to be complicated. Sometimes all you need is a cozy space, good vibes, and the sound of the ocean breeze. Come see what Chincoteague living is all about!

- 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.