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Robert's Retreat

5 Bedrooms
3 Baths & 1 Half
10 Guests
Captain's Cove
Water View
Gas Grill
Pool
Internet

Discover the ultimate family retreat in this brand new 5-bedroom, 3.5-bathroom home located in the picturesque Captain's Cove Community, boasting over 2,500 square feet of luxurious living space. With breathtaking natural marshland and water views, this residence is perfect for wildlife watching and enjoying serene sunsets from expansive decks designed for outdoor dining and recreation. The upgraded kitchen and all-new furnishings create an inviting atmosphere for making cherished memories with loved ones. Take advantage of community amenities including indoor and outdoor pools, a 9-hole golf course, fitness room, waterfront restaurant, boat ramp, and fishing pier to ensure endless fun-filled days. Don’t miss out on this exceptional opportunity to create lasting family traditions in a relaxing vacation paradise!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property does not allow pets. 

- 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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Hosta Cottage

1 Bedroom
1 Bath
2 Guests
Mainland
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

There is a fanciful quality to this secluded property where nature’s beauty and luxurious accommodations coexist in quiet harmony.    Located on the banks of Holden’s Creek, a headwater of the Chesapeake Bay and a 20-minute drive to the pristine white sand Atlantic beach on Assateague Island, The Creek Guest Cottages are private, convenient, and offer bespoke modern amenities. Explore life off the beaten path and take a true vacation. Whether you are kayaking or paddle boarding on the creek, sitting by the fire pit, biking down country roads or going to the beach, you will find plenty to do or enjoy doing nothing at all.  The views of the creek are magical at any time of the day or night from inside your cottage or from any vantage point on the 3-acre property. The cottage has been designed and decorated by a professional interior designer.

'Hosta Cottage' has partnered with our friends at Sun Outdoors Resort (located less than 2 miles from the house) so that all guests may enjoy the fun resort amenities FREE OF CHARGE. This extra bonus includes a private beach w/ water rentals, pool, playground, "snak shak", comfort stations & more! 

On-site amenities include:  a gas grill, 20’ radius fire pit, 2 kayaks, a SUP, and 2 bicycles.  There is a boat launch on the property and two docks (one floating). Linens and towels are provided.

The Hosta Cottage: 850 square ft. Full Kitchen and Laundry. French Limestone Floors and tiled bathroom. Sleeps 2 (Queen Bed). Separate Private Outdoor Dining area (not included in square footage above). Outdoor Shower. Smart TV. WIFI.

In addition to Hosta Cottage, the compound is also home to two other luxurious dwellings: Porter’s Barn and Creek House. All combined, The Creek Compound will accommodate 18 with no parking problems. Please note that this listing is for Hosta Cottage only; the other two homes - Creek House and Porter's Barn - must be booked separately. A direct inquiry should be sent for special event pricing or if you wish to rent the entire compound.

- 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. 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.

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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 home is pet friendly with an additional fee. Maximum of two dogs under 25 lbs. each; no cats. 

- 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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Seaside

3 Bedrooms
2 Baths
7 Guests
Cape Charles
Pet Friendly
Gas Grill
Internet

Welcome to "Seaside", your next relaxation haven! This charming 3-bedroom, 2-bathroom duplex offers the perfect blend of comfort and convenience, nestled in the delightful town of Cape Charles. Whether you're in town to soak up the sun at the beach or simply unwind, this property is designed to suit every aspect of your leisurely needs.

Step inside to discover a cozy atmosphere with well-appointed spaces that promise a homely feel from the moment you walk in. The primary bedroom, a restful retreat, along with two additional amply-sized bedrooms, ensures everyone has their personal space. Entertaining? The open-concept living area present the ideal setting for creating memories with loved ones.

Forget about the hassle of street parking; this house comes with its very own off-street parking spots. And for those who can't bear to leave their furry friends behind, you'll be pleased to know this home is pet friendly!

Just a short stroll away lies Central Park, where you can enjoy everything from a peaceful morning jog to a lively afternoon picnic. Need to pick up some essentials or a quick snack? There are many conveniences downtown, or the grocery store is just a little over 2 miles away—talk about convenient shopping!

Whether you're looking for a calming weekend getaway or seeking a serene place to call home for a while, this house checks all the boxes for a laid-back yet vibrant living experience. Book your stay, pack your bags, and prepare to relax—your beachside vacation awaits!

Located right next door to this beautiful duplex is "Bayside". Larger group? Bring along your friends and family and rent both units! 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation. 

- This property is pet friendly with a pet fee of $150 per pet (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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Hailey's Round House

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Screened Porch
Internet

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.

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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.

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Off Duty

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Pool
Internet

NEW FOR 2023!! New vinyl plank floor downstairs, new furniture, and paint throughout, new decking, kitchen island, outdoor shower, and tiki bar addition downstairs!   Off Duty offers 3 bedrooms, 2 bathrooms, a large screened porch, front deck with bay views, and a large outdoor space for your enjoyment. Bring your fur babies along, because this home is pet friendly! Upon entering the home, you will find yourself in awe of the large open floor plan, boasting high ceilings and tons of waterfront views for your enjoyment. Downstairs you will find two bedrooms, one with a queen sized bed and deck, as well as a bedroom that has a full sized bed and a twin bunk bed. Upstairs is an additional bedroom with a queen bed and full bath, along with a sitting area looking over the downstairs living space. Don't feel like sitting inside? Go out to the large screened in porch and enjoy the sounds of nature, or sit downstairs under the home one afternoon and enjoy some fresh catch on the picnic table while enjoying a beverage at the tiki bar. Got a boat? No problem! Off duty has a boat lift and ladder at the dock! The Captain's Cove community offers 3 pools (2 outdoor & 1 indoor), tiki bar, Marina Club and restaurant, 9-hole golf course, kids playground, dog park and more! (with fee) And you're only 20 minutes from Chincoteague & Assateague Islands (the beach), and 30 minutes from Ocean City, MD (boardwalk & amusements).

- 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.

- 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. No Sunday check-ins or check-outs are permitted.

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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.

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Windsor House

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Internet

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. 

 

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Maison des Rêves

4 Bedrooms
2 Baths
8 Guests
Cape Charles
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

This Victorian home in historic downtown Cape Charles offers a perfect blend of charming antiquity and modern amenities. With 4 bedrooms and 2 bathrooms, this house is not just spacious, but also crafted to meet all your needs with a touch of elegance.

Imagine stepping out each morning and being just a stone's throw away from the serene Cape Charles Beachfront, where the sound of waves sets a peaceful soundtrack to your day. Entertaining is a breeze with the screened front porch, and a large backyard with a deck that's perfect for hosting summer barbecues or cozy winter gatherings.

Each room is designed with comfort in mind, ensuring that every member of the family feels right at home. The primary bedroom, along with three additional bedrooms, provides ample space for relaxation and privacy. Meanwhile, the modernized kitchen is ready for your culinary exploits, whether you're whipping up a quick breakfast or a gourmet dinner.

Nearby, you have easy access to top-notch attractions like the impressive Chesapeake Bay Bridge-Tunnel and the luxurious Bay Creek Resort and Club, adding even more excitement to your neighborhood.

If you're looking for a place where historic charm meets modern living, this is it. Get ready to make delightful memories in a home that's just as unique as you are!

- 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.

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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.

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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.

- Pets are permitted with an additional fee. Limit of two dogs only. All pets must be disclosed. 

- 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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