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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.

Heron's Hideaway

3 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover your perfect family retreat at this charming three-bedroom, two-bathroom house nestled in peaceful Oyster Bay II on Chincoteague Island. 'Heron's Hideaway' welcomes up to 12 guests, making it ideal for multi-generational gatherings, friend reunions, or anyone seeking a memorable coastal escape.

The heart of this home lies in its thoughtfully designed layout, offering both communal spaces for togetherness and quiet nooks for those precious moments of solitude. Fall in love with the screened-in porch—your new favorite spot for morning coffee, afternoon board games, or listening to gentle summer rain. When you're ready for fresh air and broader views, head upstairs to the deck where peaceful vistas and cooling breezes create the perfect setting for birdwatching or evening stargazing.

The well-appointed kitchen makes meal preparation a pleasure with its dual-oven electric stove, elegant granite countertops, and full-size appliances. Families will appreciate thoughtful touches like the provided high chair, pack-n-play, and collection of board games suitable for all ages.

Located in a tranquil residential neighborhood, this trusted vacation favorite sits at the end of a quiet cul-de-sac, surrounded by lush trees and natural landscaping that creates a beautifully secluded atmosphere. You'll feel worlds away from everyday stress while remaining just a short drive from Assateague Wildlife Refuge, pristine beaches, local restaurants, and charming shops. Remote workers will appreciate the private business nook complete with desk and monitor, allowing you to balance productivity with relaxation. Since 2018, this beloved hideaway has hosted everything from girls' weekends and holiday celebrations, to hunting expeditions and peaceful solo retreats.

Whether you're seeking adventure at nearby Maui Jack's Waterpark, exploring Waterfront Park, or simply enjoying the serenity of island life, this exceptional rental offers the perfect base for your Chincoteague "home away from home" experience.

- 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: 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.

Sunset Bay Villa 206

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Charcoal Grill
Pool
Internet

Villa 206 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with private luxury bath and private exit to the waterside balcony. Villa 206 will sleep 8, and there are a total of 4 TVs. A laundry room within the unit houses your washer & dryer. Your stay also includes use of the Sunset Bay marina, pool and fitness areas. Come. Enjoy! Note: This property does not have a boat slip, however, use of the marina is included. 7-night minimum stay is required during all seasons.

- SPECIAL NOTE: This rental home has a 7 night minimum year 'round. 

- 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.

Mermaid Hideaway

1 Bedroom
1 Bath
4 Guests
Cape Charles
Internet

Escape to the Eastern Shore and discover a delightful coastal retreat that perfectly blends charm, comfort, and convenience. This one-bedroom, one-bathroom rental offers a refreshing getaway experience just minutes from the beloved Cape Charles Beachfront, making it an ideal home base for those seeking sun, sand, and seaside living.

Step inside and prepare to smile. The interior showcases a vibrant mermaid-inspired, tropical décor scheme that brings instant warmth and personality to every corner. Bold colors and playful accents create an atmosphere that feels less like a standard rental and more like a curated coastal escape. It is the kind of space that puts you in vacation mode the moment you walk through the door.

While the home comfortably serves as a cozy retreat for couples or solo travelers, it also accommodates up to four guests thanks to a convenient pull-out sofa bed in the living area. This thoughtful feature makes it equally suitable for small families or friends exploring Virginia's stunning Eastern Shore together.

Situated on the peaceful outskirts of Cape Charles, the location strikes a wonderful balance between tranquil seclusion and easy access to everyday essentials. A well-stocked grocery store is just a short drive away, and the iconic Chesapeake Bay Bridge-Tunnel provides a scenic gateway to the greater Hampton Roads region. Whether you are drawn to waterfront dining, charming boutique shopping, or lazy afternoons on the beach, everything the area has to offer remains comfortably within reach.

This affordable gem delivers an experience that far exceeds expectations. Book your coastal getaway today!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pets are permitted on the premises for an additional fee of $150 per pet, two pets 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.

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.

Serendipity

3 Bedrooms
1 Baths & 1 Half
6 Guests
Chincoteague Island
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also offers a first floor bedroom (Queen) and half bath.

- 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.

Heron Landing

2 Bedrooms
1 Baths & 1 Half
6 Guests
Chincoteague Island
Charcoal Grill
Internet

Three words : Charming. Coastal. Cottage. Located just off of Ridge Road, in the center of the island, you'll find this adorable abode. 'Heron Landing' is newly remodeled. Downstairs you'll find an open floor plan with a fully equipped kitchen - with range, refrigerator, and dishwasher. A breakfast bar to enjoy a quick bite before you head to the beach. A comfortable and cozy living area with television. A half bath and washer and dryer can also be found downstairs for your convenience as well. A small porch with sliding door is located off of the living room, allowing you to crack open to let in the island breezes flowing over Assateague Channel. Upstairs you'll find the two bedrooms, both with queen beds. Beautiful, rustic, nautical themed decor. A full bath with tub/shower is also located upstairs as well. Enjoy your cup of coffee or cocktail on the cute patio area outside, or just to get a little extra island sunshine. Memorial Park is an easy walk or bike ride down the street, with a great pier for fishing and crabbing, tennis courts, and walking paths.

- 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.

Shore Reflections

4 Bedrooms
2 Baths & 1 Half
12 Guests
Cape Charles
Town & Country
Internet

Now available and awaiting your next vacation adventure, this lovingly restored 4-bedroom Victorian home blends traditional charm with modern convenience. Nestled in a picturesque setting with beautiful landscaping and mature trees, you're just a 10-minute drive from the vibrant Cape Charles community. Explore and enjoy downtown Cape Charles, which features a pristine beach, delicious food offerings, eclectic shopping, ice cream treats, coffee shops and so much more!

Spanning 3,000 sq ft, this exquisite property features a layout with high ceilings and wood flooring throughout, enhancing the airy and expansive feel of each room. The main living spaces boast large windows that flood the home with natural light, creating a warm, welcoming atmosphere. Four generously sized bedrooms offer ample personal space for relaxation and rejuvenation. The home also includes 2.5 bathrooms, each maintaining the character of the house with tasteful touches.

Guests will enjoy a beautifully landscaped yard, ideal for leisurely days spent outdoors or entertaining guests in a serene environment. The kitchen, equipped with essential appliances, provides a comfortable space for culinary exploration and seamlessly caters to both casual dining and larger gatherings.

This property is perfect for those who appreciate the beauty of historic homes but expect the functionality needed for a contemporary lifestyle. Make your "home away from home" in a place where tradition meets comfort in the heart of Eastville, VA. Experience the unique charm of this Victorian beauty and the inviting community that surrounds it.

- No smoking is permitted on the premises. 

- Linens and towels are provided for your stay. 

- 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.

Assateague Overlook

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water View
Charcoal Grill
Internet

This property has a location that is rich with views and amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run and play, or fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen sleeper sofa). You'll also find a full bath on this level. The second floor offers a queen bedroom with a private deck that has unlimited views of the Assateague Channel. The second bedroom (upstairs) has two twin beds and you'll find another full bathroom on the second level as well. Need more space? Rent Channel Lookout next door! (Waterfront area, dock, pier and playground equipment pictured are community property at Memorial Park.)

- 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.

Surf & Turf

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Charcoal Grill
Gas Grill
Internet
Outdoor Shower

Welcome to your new coastal retreat on charming Chincoteague Island! This delightful three-bedroom, two-bathroom home offers the perfect blend of comfort and convenience for those seeking a relaxed seaside lifestyle.

Step inside to discover a thoughtfully updated interior that's clean, bright, and vacation ready! The home features not one, but two living room areas—because sometimes you need some extra space and a separate sanctuary for escaping when someone insists on watching that show you can't stand. Whether you're entertaining guests or simply enjoying a quiet evening, you'll appreciate the flexibility this layout provides.

Located just off South Main Street, you'll enjoy easy access to everything this beloved island community has to offer. Nature and fitness enthusiasts will appreciate the proximity to Veteran's Memorial Park - perfect for morning walks, afternoon picnics or letting the kiddos expel some energy! Adventure seekers can head to Maui Jack's Waterpark for family fun, while the stunning Assateague Beach beckons with its pristine shoreline and legendary wild horses roaming freely along the sand.

This modest, yet inviting, home captures the essence of coastal Virginia living without unnecessary pretense. It's comfortable, practical, and positioned in one of the most enchanting island communities on the Eastern Shore!

- 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.

Beach Haven

3 Bedrooms
2 Baths & 1 Half
9 Guests
Chincoteague Island
Town & Country
Charcoal Grill
Internet

If you enjoy being close to town and activities, 'Beach Haven' is most likely your perfect spot! Located on just one block off of Main Street, this lovely home is conveniently located to downtown Chincoteague Island, the movie theater, restaurants, famous Island Creamery, adventure park and more! The wrap around second-level deck is nicely furnished and inviting - it's the ideal place to relax with a cup of coffee in the morning or a cool drink after a long day at the beach. 

As you enter this fantastic modern home, you're greeted by an open floor plan. The main level features the living room, kitchen with breakfast bar, dining room and half bath/powder room. The lower level is entirely a two-car garage that is accessible by guests; it's a wonderful place to store your bikes or beach gear! Upstairs you'll find 3 bedrooms and 2 full bathrooms, one of them being a master bedroom en-suite. Two bedrooms feature a queen bed each, and the third (kid's) bedroom features a bunk bed (2 Doubles) and a Twin bed. 

Lets talk electronics! This home has been carefully and tastefully furnished for the discerning traveler. The living room and all 3 bedrooms all have large Smart TVs, and the kid's bedroom includes an HDMI cable for easily connecting gaming consoles, etc. You'll also enjoy amenities such as keyless self check-in and check-out.

Come for a week in the summer, or come for a shorter stay in the spring or fall. 'Beach Haven' is available year-round and the island is gorgeous the whole year through!

- 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.

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