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Our Happy Place

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Discover your own piece of paradise at this incredible beach getaway! 'Our Happy Place' is the perfect retreat for up to 7 guests seeking comfortable, tastefully decorated accommodations. This cozy vacation home is clean, simple, and fully furnished, including amenities that will make you feel right at home. Even your furry, 4-legged family members can join in on the fun, small to medium dogs are welcome.

Situated in the desirable Oyster Bay I waterfront community, 'Our Happy Place' is located at the end of a wide-mouth canal, offering unobstructed water views and a private dock platform. You'll love the convenience of being situated next to the community boat ramp, making it easy to launch your watercraft for a day of adventure.

Relax and unwind on the expansive wrap-around screened porch overlooking the water, featuring plenty of comfortable seating and a dining area. Savor your morning coffee or sip a cool drink after a day at the beach.

'Our Happy Place' is a single-level home with 3 cozy bedrooms that can accommodate up to 7 guests. The bedrooms include 1 queen, 2 twins, and 1 bunk bed (twin over double). There are 2 full bathrooms, one of which is a tub shower combo.

- 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.

The Sea Horse

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

We are pleased to offer 'The Sea Horse'! This fabulous home features a spacious, open floor plan with room for the whole family - and even the furry family members! The grand room downstairs features an open kitchen and dining space with center island, and the living room with large windows that allow natural lighting. There are French doors that open up to the wonderful screened porch - perfect for enjoying morning coffee or cool drinks after a day at the beach! To compliment the outdoor space, there's a fenced yard that's perfect for the pup! The master bedroom (King bed) with en suite bathroom, as well as a second bedroom (Twin bed) and full bathroom complete the downstairs space. Upstairs is where you'll 2 more sleeping areas/bedrooms - one with a Queen bed and the other with 2 sets of bunk beds (Twin over Full each). Clean, modern and comfortable, you're sure to love all that 'The Sea Horse' has to offer. From the beachy-chic decor and design, to the fully stocked kitchen and open spaces, there's nothing left undone. Come and see for yourself!

- 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: two pet 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.

Oyster Shack

3 Bedrooms
2 Baths & 1 Half
8 Guests
Cape Charles
Town & Country
Pet Friendly
Internet
Outdoor Shower

Introducing the newest gem in Cape Charles! Perfect for those seeking a serene retreat, this charming vacation rental boasts three cozy bedrooms, including a spacious primary bedroom, complemented by two and a half well-appointed bathrooms. Nestled in the heart of town, this delightful home invites comfort and exudes modern elegance.

Step inside to discover a beautifully crafted layout where each square foot is maximized for enjoyment and ease. You'll love the convenience of your own peaceful backyard, ideal for morning coffees and evening relaxation. Plus, it’s a pet-friendly haven, so your furry friends can join in on the fun!

Staying here, you're seconds away from sinking your toes in the beautiful beach, ensuring endless days of sun-soaked adventures. Need a break from the sun? Dive into the refreshing experiences available at the nearby at Cape Charles Mini Golf!

For those who love cooking with fresh ingredients, the local Beach Market is just a short trek from your doorstep, making it nearly effortless to gather necessities for a spontaneous beach picnic or a cozy family dinner.

Whether you’re in for a weekend getaway or a longer relaxing stay, this house is more than just a place to stay—it’s the backdrop for your next chapter of cherished memories! Ready to kick off your sandals and stay a while? This Cape Charles beauty is waiting to welcome you! 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee of $150 per pet. All pets must be disclosed prior to arrival. 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.

 

Cockleshell Cottage

3 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage! This modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs features 2 more bedrooms (Double and Double/pull-out Twin trundle), and a full bathroom. Cockleshell Cottage is handicap accessible. Relax and enjoy the breeze on the open front porch or back screened porch. Call us today; this home books fast!

- 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 two small dogs 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.

Porter's Barn

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

Porter's Barn, where luxury meets seclusion on the water's edge...

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, Creek House 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 Cottages have been designed and decorated by a professional interior designer.

'Porter's Barn' 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! 

Shared amenities include: a gas grill, 20 ft. 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.

Porter's Barn: 900 square ft. Full Kitchen and Laundry Room. Marble Bathroom. Sleeps 2 (Queen Bed). Outdoor Shower. Smart TV. WIFI

In addition to Porter's Barn, the compound is also home to two other luxurious dwellings: Hosta Cottage and Creek House. All combined, The Creek Compound will accommodate 18 with no parking problems. Please note that this listing is for Porter's Barn only; the other two homes - Creek House and Hosta Cottage - 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. Limitations: one dog only. No pets on the furniture, please.

- 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.

Anchors Away

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Pet Friendly
Gas Grill
Pool
Internet
Outdoor Shower

Welcome to "Anchors Away," a captivating waterfront home now available for rent, offering an unparalleled living experience. This remarkable property boasts four generously sized bedrooms and three well-appointed bathrooms, providing ample space for comfort and privacy.

Nestled in a vibrant community known for its welcoming atmosphere and scenic beauty, this home is designed to impress with its stunning waterfront views that can be enjoyed from the spacious decks - perfect for entertaining or simply unwinding in nature's embrace.

The first-floor suite offers convenience and accessibility, ensuring that everyone can enjoy this home's charm without compromise. The interior is just as impressive, featuring granite countertops and stainless appliances that add a touch of elegance to the functional and stylish kitchen. 

With parking space for up to four vehicles, you'll find this property not only beautiful but also practical. The pet-friendly policy ensures that your beloved companions can join you in calling "Anchor's Away" home.

This house is more than just a place to vacation; it's an opportunity to make life-long memories for those who value beauty, community, and comfort. Whether you're gazing at the serene waters from your deck or enjoying the modern amenities inside, this home invites you to live your best life.

Don't miss the opportunity to make "Anchor's Away" your new haven. Contact us today to experience firsthand everything this exceptional rental property has to offer.

- 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: 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.

- 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. 

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.

Southern Dream

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water View
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Charming 3 bedroom ranch home located in one of Chincoteague Island's residential communities. Nice, quiet location with a water view of Oyster Bay. You'll enjoy the easy, one-story floor plan with open living room/kitchen/dining areas. If you love the outdoors, spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high speed internet, charcoal grill and an outside shower will ensure your comfort during your 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.

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.

Channel Watch

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Located down a gravel road that runs parallel to Assateague Channel, you'll find Channel Watch nestled in between the pine trees. The perfect getaway on Chincoteague Island for you and your family! On the ground level you'll find a bedroom with King bed and sitting/television area, an open-floor plan for the living area with plenty of comfortable seating, a fully-equipped gourmet kitchen, and a dining area with table for enjoying family meals together. There is also a large screened in porch area with seating if you want to take in the views and enjoy that meal outside - and honestly, why wouldn't you? A full bath is also located in the hallway downstairs too. Upstairs you'll find two more bedrooms. The master featuring a roomy king bed and private balcony overlooking the water, and the other bedroom with two beds - one Queen sized and one Full size. A full bath is also located upstairs, as well as a utility closet with a full size washer and dryer. Enjoy the island sunshine and cool breezes coming off the water off of the private dock in the back. Bring your fishing poles and crabbing gear, and haul in a bounty to prepare back at the house. Or ride the bike to one of the many favorite restaurants located just up the street on Beach Road - The Village or AJ's for something a little more upscale, or maybe tacos from Pico or a pizza from Famous for something a little easier. You're sure to find something to please everyone! If you happen to be an early bird, you're in for a real treat when it comes to sunrises at Channel Watch. Brew yourself a cup of coffee and take it out on the pier with you, take a seat, and wait for the show. It's just for you. Bring your family and come experience island life for yourself at Channel Watch.

- 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.

Blue Point

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come for an old fashioned family vacation. This wonderfully maintained classic Chincoteague-style home features a large screened porch and beautiful, spacious yard for those warm summer evenings. A great enclosed outside shower comes in handy for rinsing the sand off after a long day at the beach. Downstairs there is a family room with a wood stove, living room/library with a TV and an eclectic selection of books, a formal dining room, full bath and kitchen. Upstairs there are three bedrooms and a full bathroom. Bring your kids and pets along, there is plenty of room to play!

- 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.

Lighthouse Estates #8

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Water View
Pet Friendly
Boat Dock
Charcoal Grill
Pool
Internet

Welcome to Lighthouse Estates #8, formerly known as 'Natalie's Nook'! This 2 bedroom beach retreat is located in the popular Lighthouse Estates community on the East Side of Chincoteague Island. Enjoy all the amenities and features one could desire during their vacation - a pool, water & lighthouse views, a pier perfect for fishing, crabbing or kayaking, not to mention a vacation rental filled with all the comforts of home! Downstairs you'll find an open floor plan with living room, kitchen, dining area and powder room. Upstairs features 2 bedrooms (one master ensuite with private bathroom and water view balcony) and a full bathroom off the hallway. Lighthouse Estates #8 is conveniently located to The Pearl Restaurant, the waterfront Memorial Park, boat rentals, the Town public boat ramp & more! Come for a fabulous, relaxing stay! . 

- 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 dog, 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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