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Princess Anne

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Welcome to the Princess Anne condominium in the heart of charming Cape Charles. Ideally positioned just blocks from the beachfront, this beautifully curated home offers a comfortable balance of modern upgrades and downtown accessibility.

Step into an open living area that features a cozy fireplace and large television, perfect for unwinding after a day by the shore. A full kitchen lets you whip up a quick morning coffee or cook a meal, all in the comfort of your own space..

Take advantage of the rooftop terrace which offers relaxation while overlooking downtown and the Bay after a long day at the beach. Complete with a wet bar area under a pergola, this is sure to become one of your favorite hangout spots. 

The primary bedroom offers a private retreat with its own balcony — an ideal spot for enjoying gentle breezes. An adjacent custom-tiled bathroom adds convenience and a touch of refinement.

Outdoor enthusiasts and leisurely strollers alike will appreciate the condo's proximity to the Cape Charles Beachfront, mere minutes away on foot. The neighborhood's inviting walkability extends to nearby restaurants, ice cream parlors, boutique shops, and local art galleries. Just a short drive away, you'll find grocery, convenience, dollar, and liquor stores stocked with everything you need for your vacation.

If convenience, style, and coastal charm are on your checklist, this condo just might check every box. With a location that makes spontaneous ice cream excursions and sunset beach walks a regular thing — it isn't just a rental, it's a lifestyle.

- 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

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 property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. Pet Restriction: Small dogs only under 35 lbs. NO CATS. 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.

All Done

3 Bedrooms
3 Baths & 1 Half
8 Guests
Chincoteague Island
Water View
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

All Done is located on the popular East Side Road, just minutes from downtown, Maddox Blvd (Beach Road), Memorial Park and the beach on Assateague Island. There are snippet water views of the Assateague Lighthouse and Channel. It is a brand-new home just built in Spring of 2024, and features an open first floor plan joining the kitchen, dining and living rooms into one, as well as a first floor bedroom with full bath. The second floor has 2 more bedrooms including individual full bathrooms, with a walk-in shower in the primary bedroom. There is a spacious laundry room also conveniently located on the second level. The outside of All Done includes a screened porch on the side of the home, and a spacious front porch with ample rockers to enjoy the sunsets over the tree line. There is also a charcoal grill, a large yard for games and parking for up to 4 cars.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $20 per pet, per day will apply. Maximum pets allowed: 2. 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.

 

An Unfettered View

2 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Internet
Outdoor Shower

This beautiful 2 bedroom ranch home has a quiet, out-of-the-way location situated on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck. It's perfect for crabbing, kayaking & canoeing! An Unfettered View features all amenities including a private master suite with full bath, central air, all appliances including dishwasher, washer/dryer, wireless internet service and a wonderful family room on the waterside of the home. Tastefully furnished and very accommodating, this is a great vacation spot! An Unfettered View is wheelchair accessible.

- 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.

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. 

Shell Cottage

4 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water View
Pet Friendly
Gas Grill
Internet
Outdoor Shower

Come and enjoy a delightful vacation at "Shell Cottage"! Located on the popular East Side of Chincoteague Island, you'll enjoy water views of the Assateague Channel and lounging on the outside decks (one which includes an outside shower). This open floor plan home features two bedrooms downstairs (both with a queen bed and a TV each), a half bathroom, and spacious living room & kitchen. Upstairs you'll find 2 more bedrooms (one with twin trundle and the other with 2 twins) and a full bathroom. Just a short drive to the Memorial Waterfront Park, public boat launch, downtown area and restaurants! Shell Cottage also includes all the modern conveniences such as wireless internet, washer/dryer, dishwasher and more. And you'll have room to park your boat and trailer. This just may be your perfect vacation spot!

IMPORTANT NOTE: The hot tub is CLOSED until Spring 2027.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 4.  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.

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. An additional fee of $200 per pet will apply. Maximum number of pets allowed: 2. 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.

High Tide

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet
Outdoor Shower

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.

Bay Breeze Retreat

6 Bedrooms
5 Baths & 1 Half
14 Guests
Cape Charles
Town & Country
Gas Grill
Screened Porch
Pool
Hot Tub
Internet
Outdoor Shower

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.

Belle of the Bay

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

Truly the "Belle of the Bay", this beautiful custom waterfront home is tucked away at the very tip of one of Chincoteague's most popular residential communities - Oyster Bay I. This means you'll enjoy unobstructed 360 degree water and marshland views from nearly every space in the home. The decor and local art collection alone will "wow" you! Watch the sun rise as you sip your morning coffee from the balcony or screened porch. Enjoy the quiet and privacy as you watch the wildlife that surrounds this fabulous property. The main house features 3 bedrooms, 2 full bathrooms, and an additional loft sleeping area (twin trundle bed). The detached garage features another living area/bedroom (2 Twin beds) that is available for guest use (lower level garage is not accessible by guests). NOTE: Living room fireplace is not functional. 

- 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.

Stella del Mare

3 Bedrooms
2 Baths & 1 Half
10 Guests
Chincoteague Island
Water View
Charcoal Grill
Internet
Outdoor Shower

Stella del Mare - or "Star of the Sea" in Italian - is about as charming as it gets. Located on South Main Street, this beautiful newly-remodeled home has everything you could want in a coastal cottage. Enjoy coffee on the front porch while watching the island come to life in the morning, or sip on a cocktail while waiting for the sun to set. The ground floor features an open floor plan with fully equipped kitchen - gas range, refrigerator/freezer, dishwasher, coffee maker. A beautiful breakfast bar area, as well as dining area. And a beautifully decorated living area with tv. The master bedroom is located on the ground floor featuring a king bed and full bath attached. Another full bath is located on the ground floor as well. On the second floor you'll find two additional bedrooms - one with two full beds, and the other with twin bunks, as well as a comfortable futon. Perfect spot for the kiddos! A comfortable living area in the middle to put a movie on for the kids. There is also a full bath located upstairs as well. Walk downtown for some shopping, then come back to the house and order a cheesesteak from the best sub shop in town - located just across the street. Or, maybe you'll catch a whiff of the oyster fritters frying down at the carnival grounds and walk down to sample one. Go ahead, you're on island time! Newly added patio on the back with lovely seating area to enjoy your meals al fresco, or just to sit and chat and enjoy the sunshine. You're sure to find plenty to put a smile on your face at Stella del Mare - the star of the sea. Floor plan: Downstairs (main level) features an open living/dining room and kitchen with breakfast bar. The master bedroom with connected bathroom (tub and shower) is also downstairs. Upstairs there's an open living room/sitting area, a full bathroom (with separate shower and tub) and two more bedrooms. One bedroom features a Double and Queen bed, and the other bedroom features a bunk bed (2 Twins) with a pull-out Twin trundle, as well as a Queen size futon. There is a portable Pack-n-Play crib and high chair for guest use as well.

 If you're traveling with a larger group but like the separate of "your own place", check out 'Stella Della Baia' ! 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. 

- 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.

Hill House

4 Bedrooms
2 Baths & 1 Half
9 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has been renovated, along with the bathrooms. Excellent in town location - walk to dinner, movie, shopping & galleries. Enjoy the beautiful Chincoteague sunsets with a beautiful water view! Hill House features 4 bedrooms and 2.5 bathrooms, with a first floor bedroom (double/twin Bunk) & 1/2 bath. Three more bedrooms on the second floor with a master suite (king) that offers a private staircase to the dining room. The third bedroom (queen) and fourth (two twins) are also located on the second floor. Enjoy the modern amenities of this lovingly restored island home, all while being in the middle of downtown Chincoteague's happenings.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 4. 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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