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Windsor House

3 Bedrooms
2 Baths
8 Guests
In Town
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. 

 

Shady Grove

4 Bedrooms
2 Baths
8 Guests
North Main
Water View
Internet

Come and relax at this fabulous beach home that is tucked away on the quiet northern end of Chincoteague Island! Aptly named, "Shady Grove" is situated in a natural marshland grove in the Richardson's Landing community. Features include 4 bedrooms, 2 bathrooms, numerous updates and remodeling and a bright, open floor plan. Come and see for yourself - you won't be disappointed!

- 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.

Star of the Sea

3 Bedrooms
2 Baths
8 Guests
In Town
Town & Country
Pet Friendly
Gas Grill
Internet

Introducing a charming, newly renovated house, offering a perfect blend of comfort and convenience. This single-family home features an inviting sunroom, a brand-new kitchen, four well-appointed bedrooms, including a serene primary bedroom, and two modern bathrooms, all professionally decorated with a delightful beach theme.

Designed to accommodate up to eight guests, the house boasts spacious rooms that ensure ample space for relaxation and entertainment. The living areas flow beautifully outdoors to a superb deck, ideal for enjoying your morning coffee or sunset dinners, surrounded by a spacious yard.

Nestled in a vibrant neighborhood, the property promises a vacation of ease and accessibility. It’s centrally located near the heart of the town, close to a pristine beach, restaurants, and family-friendly activities, including mini-golf and Maui Jack's Waterpark. Nature enthusiasts will appreciate the proximity to the Assateague Island National Seashore, a spectacular location for wildlife and scenic views, while the nearby Downtown Chincoteague Waterfront Park provides excellent opportunities for leisurely activities.

Experience the joy of living where every day feels like a vacation. This retreat is not just a place to stay, but a home away from home. Come and see for yourself!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Home is pet friendly with additional pet 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.

Admiral Benbow

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet
Outdoor Shower

A very nice contemporary home located in Oyster Bay I community. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner! The variety of bed sizes allow the perfect set up for families of all ages! Come and stay at this classic Chincoteague home but don't delay; it books quickly!

- 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.

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.

Seas the Day

3 Bedrooms
2 Baths & 1 Half
8 Guests
In Town
Screened Porch
Pool
Internet

You will LOVE the quiet duplex community where this home is situated. Bright, open floor plan, with adjoining screened and open-air porches - perfect for sipping coffee in the morning or relaxing with a cool drink after a day at the beach. The first floor bedroom offers a private bathroom and the sweetest window nook - bring your book! Two additional bedrooms upstairs share a full bathroom and all bedrooms are tastefully decorated in their own fun personal themes! Hosting a group that requires more space? Rent Seas The Day's sister, 'Sea La Vie', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bunk bed + a Twin Trundle 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.

High Tide

3 Bedrooms
2 Baths
9 Guests
Piney 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 snipet 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.

Sunset Bay Villa 312

3 Bedrooms
2 Baths
8 Guests
Sunset Bay
Waterfront
Pool
Internet

Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are TVs in all the bedrooms, and a computer desk to work from. Villa 312 will sleep 8, and features lots of extras including beach gear and baby gear for your use, as well as a 14' boat slip. Your rental also includes the use of the Sunset Bay pool and fitness area. Located adjacent to our historic downtown area, where you'll find gourmet food shops, boutiques, a public library, galleries and fine dining - all with a short stroll. Come and enjoy a Sunset Bay vacation! | Note: This villa has access to a 14' boat slip.

- 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.

Wildflower

3 Bedrooms
3 Baths
6 Guests
South Ridge
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is a second screened porch overlooking that water from the great room. The second level has a large waterfront master suite with a private balcony, two more bedrooms and another full bath. Close to Memorial Park right across the street from a family restaurant! (Spiral staircase in home, may not be suitable for small children.) For larger groups for family reunions, check out nearby Moon Rising or Herbie's Hideaway!

- 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 Exposure

4 Bedrooms
2 Baths
7 Guests
Piney Island
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

Southern Exposure is nestled along the natural shoreline of the Assateague Channel, offering some of the most beautiful water views on Chincoteague Island. Conveniently located in one of Chincoteague's most popular residential communities, you're only minutes from the beach and attractions - shopping, mini golf, restaurants and more! This ranch-style home features 4 bedrooms, and all your main living areas, on one level. Enjoy relaxing moments on the waterside screened porch or private deck overlooking the marsh and Assateague Channel. And you can crab/fish, kayak or dock your boat from the deep-water pier (with ladder and floating dock). It doesn't get much better than this!

- 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.

Gone Coastal

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet

Enjoy the cool breezes coming off the Chincoteague Channel while relaxing on the porch at Gone Coastal! Nestled in a grove of pines and tucked just off East Side Drive, this charming unit has everything your family desires for a wonderful stay on Chincoteague Island. Bright and cheery nautical decor will help to put you on "island time". Featuring two bedrooms, two and a half baths, a spacious living and dining area, and a fully-equipped kitchen. The two bedrooms are on the upper level. The master features a full bed with flat screen television, full bath, and balcony with sliding door and comfortable outdoor furnishings. An additional bedroom featuring a full size bed and double bunk, and a full bath is located in the hallway upstairs as well. On the ground floor you'll find a spacious living area with large flat screen tv, plush seating, and plenty of reading material. The eat-in kitchen features everything you'll need to prepare and enjoy meals "at home" - electric range, roomy refrigerator, dishwasher, coffee bar, and dining table. A full-sized washer and dryer are located in a utility closet just off the kitchen, and a barbecue grill is located on the back porch for your convenience. Located centrally on the island - you're a quick bike ride or easy walking distance to the commerce on Maddox Boulevard or downtown Main Street, or to Memorial Park located just down Eastside Drive. Pop into one the oyster farms and grab a sack to bring back and enjoy with a glass of wine as the sun sets on another day Gone Coastal. Please Note: No boats or trailers are allowed at the complex.

- 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.

Stella del Mare

3 Bedrooms
2 Baths & 1 Half
10 Guests
South Main
Water View
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.

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