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Hill House

4 Bedrooms
2 Baths & 1 Half
9 Guests
In Town
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 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.

Oasis on Main

3 Bedrooms
1 Baths & 1 Half
11 Guests
In Town
Water View
Pet Friendly
Gas Grill
Screened Porch
Internet

Welcome to 'Oasis on Main"! This charming and lovingly restored traditional Chincoteague-style home is ready to welcome you with open arms. Nestled in the heart of downtown on the bustling Main Street, this property offers a unique blend of convenience and tranquility. As you approach this stunning house, you'll be immediately captivated by its striking curb appeal. The beautiful landscaping and gardens surround the property, creating a serene oasis that will make you feel right at home. Imagine enjoying your morning coffee on the front porch (the coffee shop is right next door!), all while soaking in the sights and sounds of the vibrant town. Step inside to discover a tastefully restored interior that seamlessly blends classic charm with modern comforts. With three spacious bedrooms and one and a half bathrooms, there's plenty of room for everyone to have their own space. The open layout creates an inviting atmosphere, perfect for entertaining guests or simply enjoying quality time with your loved ones. The kitchen boasts all the amenities a culinary enthusiast could dream of, from sleek countertops to ample cabinet space. Whether you're preparing a quick snack or hosting a dinner party, this kitchen is sure to inspire your inner chef. One of the standout features of this property is its location. Situated next door to a cozy coffee shop, you'll never have to go far for your caffeine fix or a delightful pastry. Additionally, being conveniently located near 'Beach Road' means that shops, restaurants, mini golf, ice cream and more are just a short jaunt away. Are you a pet lover? Good news - this property is pet friendly! Your furry friends will adore exploring the spacious backyard while you relax in the screened gazebo, savoring every moment of the outdoors. With three parking spaces available, finding a spot for your vehicles will never be an issue. Don't miss out on this opportunity to make Oasis on Main your newest vacation "home away from home". The combination of its historic charm, convenient location, and modern amenities is truly irresistible. Book today - this one won't last long!

- 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.

 

Tall Pines

2 Bedrooms
1 Baths & 1 Half
6 Guests
Piney Island
Water Access
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room.Tall Pines has two bedrooms, one with a queen, and other featuring two twins. There is also an air mattress for guest use.  Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall Pines is pet friendly with and outdoor dog run in the yard. You won't be disappointed! | | Note: Water access is a shared with the community just a short distance from the rental home.

- 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.

Grandview

4 Bedrooms
4 Baths
10 Guests
North Main
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Internet
Outdoor Shower

Enjoy stunning sunsets from this 5 star home at water's edge. Relax with the amazing water view from the north side of the island. Every bedroom is a suite, to ensure all of the adults have the right amount of privacy and a quiet place to stow away with a book. The dining area is big enough to accommodate large family dinners and the kitchen has been newly remodeled and upgraded! With a breakfast bar and wide open living area, you can be sure to have lasting family moments together. Have your cameras ready to capture the changing tides, wildlife and those crazy family moments that are sure to happen in this lovely home. Grandview offers every amenity from a screened porch, an open deck, long pier with a dock, ceiling fans throughout, wireless internet and much much more! This home also includes the use of 2 kayaks.

- 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. 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.

Highlander

3 Bedrooms
2 Baths & 1 Half
9 Guests
In Town
Pet Friendly
Screened Porch
Internet

Welcome to 'Highlander', a charming ranch-style home nestled in a quiet residential neighborhood. This delightful 3-bedroom, 2.5-bathroom house offers the perfect opportunity to create lasting vacation memories in a cozy and inviting space. As you step inside, you'll immediately appreciate the convenience and comfort of this one-floor gem. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating an ideal space for gathering family and friends. Imagine hosting get-togethers where conversations flow effortlessly from one room to another. The living room is a warm and welcoming retreat, complete with a fireplace that sets the stage for cozy evenings spent curled up with your favorite book or enjoying quality time with loved ones. During warmer months, embrace the tranquility of nature on your very own screened porch - an idyllic spot to relish the gentle breeze while savoring a cup of morning coffee or simply unwinding at the end of the day. For those who appreciate al fresco dining or outdoor gatherings, the backyard patio awaits your next outdoor retreat. Transform it into an oasis where barbecues and laughter fill the air, or create a serene retreat where you can recharge amidst greenery. This property's location offers the best of both worlds - a peaceful haven away from the hustle and bustle, yet conveniently close to amenities. The "Beach Road" is just moments away, providing easy access to the beach and refuge, refreshing coastal breezes, and endless opportunities for recreational activities like swimming, sunbathing, or simply strolling along the shore. With three well-appointed bedrooms and two-and-a-half bathrooms, this home provides plenty of space for everyone to find their own sanctuary. Whether you need a dedicated home office or desire a separate playroom for little ones, there's flexibility within these walls to accommodate your unique lifestyle needs. Never worry about parking again - this property boasts three parking spaces, ensuring you and your guests always have a convenient place to park. This is more than just a house; it's a place where memories are made and vacation dreams unfold.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pet friendly with fee.

- 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.

Charlie's Bayside Retreat

3 Bedrooms
2 Baths & 1 Half
8 Guests
South Main
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

This is it! Are you looking for your perfect vacation getaway spot? Look no further. 'Charlie's Bayside Retreat' is everything you'll need for your home away from home, at the beach! The first main level features an open floor plan with a living room that opens up to a wonderful screened porch with comfortable outdoor dining furniture. The open living area also features a large Smart TV with cable and an electric fireplace. A modern kitchen that is fully stocked with everything you could possibly need, also has new appliances and a Keurig coffee maker, breakfast bar, open dining area, and powder room complete the first-floor living space. On the second floor, you'll find two bedrooms, one with a Queen bed and Smart TV and the other with 2 Twins & a Full - both with balconies and a shared full bathroom with dual sinks. The entire third floor is a spacious, private primary oasis with a Queen bed, and a luxurious en suite featuring a deep jetted tub and dual sinks. This bedroom is also equipped with a Smart TV and a balcony with amazing views & Adirondack chairs making it perfect for relaxing or sunbathing. Additional features of this fabulous vacation home include your own private boat slip (#7), pier for fishing and crabbing, fish cleaning station, covered parking area, grill, picnic table, and tons of extras! There's an outdoor shower, and beach gear including beach chairs, beach toys, and an umbrella. Not to mention you're conveniently located on South Main Street - walk to the downtown area (including Ropewalk for food and drinks) or to the annual Fireman's Carnival. The possibilities are endless. Some of the most gorgeous sunsets ever witnessed are from this spot on South Main Street & it is the perfect spot to watch rocket launches from Wallops. It doesn't get much better than this!

- 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.

Hidden Treasure

4 Bedrooms
3 Baths
10 Guests
North Main
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

"X" marks the spot here at Hidden Treasure. Nestled in a cove along the shoreline of the island's most exclusive neighborhood on the northern end, you'll have everything you need for a perfect family vacation. ENDLESS outdoor space in the form of a long private dock with a large sitting area at the end, huge deck off the living area overlooking the water, a screened in dining area off the deck, and a large shared balcony off of two of the bedrooms on the upper level. The spacious home offers 4 bedrooms and 3 bathrooms. On the ground level you'll find the fully-equipped kitchen with breakfast bar and dining area. The kitchen opens up to the cozy living area, with a fireplace and an unbelievable view of Chincoteague Bay. You'll find plenty of seating for your family, just around the corner is another sitting area for overflow - or if you just want to curl up with a good book alone (no judgement!). Also located on the ground level is a full bath and bedroom with two twins - ideal for putting the little ones to bed but still being able to keep an eye on them. Upstairs you'll find the other 3 bedrooms. The master suite - furnished with a king bed, bath with Jacuzzi soaking tub and shower, flat-screen, and yet another knockout view on the balcony. The balcony runs the length of the house and is shared on the other end with a bedroom with a queen. An additional full bath, and another bedroom with two twins is also found upstairs as well. Crab and fish right off the dock, and enjoy cooking and enjoying your bounty together al-fresco at the screened-in porch on the deck. Or pour yourself a nice chilled beverage and walk down to the end of the dock and wait for the sun to slip under the horizon over Chincoteague Bay - bringing the end to another day of treasured memories made at Hidden Treasure.

- *NEW FOR 2025: Level 2 EV charger!*

- 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.

Timeout

2 Bedrooms
1 Baths & 1 Half
6 Guests
In Town
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to your island getaway! This charming 2-bedroom cottage offers the perfect blend of comfort and coastal living. Lovingly renovated with care, this rental home captures the relaxed spirit of Chincoteague Island.

Step outside to enjoy the screened porch where you can sip morning coffee while listening to seabirds or unwind in the evening with a cold beverage. The inviting backyard is ideal for soaking up sunshine or enjoying a cookout on the gas grill.

Water enthusiasts will appreciate the kayak provided for exploring the island's scenic waterways. For land adventures, hop on one of the two bikes to cruise around town. When you're feeling competitive, challenge your companions to a friendly game of croquet or cornhole — all equipment included!

Your four-legged friends are welcome to join in the island fun, as this property is pet friendly.

Location is a true highlight! Just a short stroll away is the Downtown Chincoteague Waterfront Park, perfect for picnics and people-watching. For family adventures, Maui Jack's Waterpark offers splashy fun just minutes away. The crowning jewel of the area—Assateague Beach—is a quick drive from your rental, where you can witness the famous wild ponies and enjoy pristine shorelines.

Experience the casual, laid-back lifestyle of Chincoteague Island in this cozy home that's the perfect launch pad for creating unforgettable vacation memories!

- 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.

Sea Charm

3 Bedrooms
2 Baths
8 Guests
In Town
Charcoal Grill
Screened Porch
Internet

Charming in-town 3 bedroom home with a day-bed alcove, 2 baths, large fenced yard, carport and screened porch. Located on a quiet street, but a short walk to downtown shopping, movies and restaurants. Expanded Master Bedroom with claw foot tub and king size bed. 

- 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.

The Great Escape

5 Bedrooms
3 Baths
11 Guests
Cape Charles
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover the charm of Cape Charles in this beautifully restored 5-bedroom, 3-bathroom house, available for your next vacation adventure. Nestled in the heart of downtown, "The Great Escape" places you just minutes away from a vibrant selection of shopping, dining, and entertainment options, including local ice cream shops and mini-golf. Whether you're enjoying the bustling town scene or relaxing at home, this property offers both convenience and comfort.

Step onto the inviting open front porch where you can sip your morning coffee while soaking in the town views. Alternatively, the screened porch provides a tranquil retreat to unwind in the evenings without the pesky insects. Inside, you’ll find a clean and comfortable interior with ample living space that caters to both large and small families alike.

"The Great Escape" is ideal for those seeking a blend of small-town charm and modern amenities, all within walking distance of Cape Charles' delightful attractions. Whether you're settling down with your family or looking for a scenic change of pace, this vacation home promises a lifestyle of ease and excitement. Don’t miss out on making this house your new home away from home — book your getaway today!

- 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.

 

Seahorse Cove

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

Welcome to Seahorse Cove! This is an adorable 3 bedroom, 2 bathroom home that has been completely renovated. You will not be disappointed - from the personal touches, to the decor and amenities this lovely home has to offer - no detail has been left untouched. As soon as you enter, you will immediately fall in love with the bright, beachy colors, and the overall feeling of complete relaxation. Seahorse Cove offers a fully equipped kitchen with stainless steel appliances, granite countertops, a breakfast bar, and all of your cooking essentials for providing a delicious meal. Enjoy the sounds of nature from the cozy screened porch, while sipping your morning coffee or enjoying an evening beverage. The owner's suite is furnished with a comfy rocker, plush bedding and a private bath with a tiled shower.  You will also find two additional bedrooms on the opposite end of the home, along with another full bathroom. There is plenty of room outside to enjoy, or to let your fur baby play. 

This home is conveniently located to all the community amenities such as pools (2 outdoor & 1 indoor), fitness center, marina w/ fishing pier, restaurant, tiki bar, and more! If day-tripping is more your style, you'll love the fact that this home is located only 20 minutes from Chincoteague Island and the beach, or 30 minutes to Ocean City, MD and the boardwalk amusements. 

- 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: 2 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.

- 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. 

Off Belay

4 Bedrooms
3 Baths
8 Guests
North Main
Water View
Gas Grill
Screened Porch
Internet

Welcome! This spacious, luxurious home offers everything you need for a relaxing vacation. Located in the Smugglers Cove community, Off Belay is situated on a small creek, perfect for any nature enthusiast. Upon entering this gorgeous vacation home, you will be enamored with the thoughtful décor and tasteful furnishings. Beautiful hardwood floors lead you to the gourmet kitchen with an expansive kitchen island, including a 5 burner gas range. The living room boasts high ceilings,  plenty of seating,  a wood burning fireplace, and tv as well as access to the large screened in porch and open deck. The first floor also offers a primary queen suite with an attached bath (shower only), and a private den with tv and a queen sleeper sofa. You will also find another full bathroom, washer/dryer and utility sink just down the hall. Upstairs, there are two more bedrooms: a king room with a jack and jill bath as well as a twin room. Walk out to the large deck from the second floor and take in all the views Off Belay has to offer! There is plenty of out door space for entertaining, sitting and relaxation. 

- 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.

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