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Herbie's Hideaway

3 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beautiful views of Assateague Island. The oversized chef's kitchen offers ample room for family gatherings and preparing meals, and it compliments the spacious dining area that opens up to the large screened porch. Beautiful custom windows and large sliding doors complete the open and airy floor plan. The geothermal heating/ac system lends to your ultimate vacationing comfort! Close to Memorial Park (playground, basketball, tennis, trails, water access) and directly across the street from a family restaurant! For larger groups or family reunions, check out nearby Moon Rising or Wildflower!

- 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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Misty's Thicket

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Charcoal Grill
Screened Porch
Internet

Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends. Upstairs, you find a great master bedroom with en-suite, a full bathroom off the hallway, and a second bedroom that features a bunk bed and a queen size bed that looks out onto the second-level screened in porch affording amazing Chincoteague Island views.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pets are not 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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Charlotte's Morning Sun

4 Bedrooms
4 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Set in the boutique residential community of Oyster Bay I, 'Charlotte's Morning Sun' is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms, one of which has it's own balcony that feels like it's floating on water. The stylish design offers private and peaceful lounge and dining areas that embrace sweeping bay views that stretch uninterrupted to the horizon. A state-of-the-art chef's kitchen, a generously-sized waterside screened porch as well as a large observation area allows effortless indoor outdoor living. On the first level you'll find the living room, observation area, chef's kitchen, dining area, 2 bedrooms and a wonderful waterside screened porch. Upstairs you'll find 2 more bedrooms, one with a private balcony. Outside, enjoy exclusive access to the bay via a private dock/boat-slip, or bathe in the outdoor beach shower surrounded by a grassy coastal garden. Just a short drive to the beach, local restaurants and shops, 'Charlotte's Morning Sun' offers an opportunity to secure a luxury vacation home in an exceptional setting. Note: The Oyster Bay I community where this property is located offers a boat ramp that is exclusive to the homes in this community. Water depth may not be suitable for all boats and dock/ramp usability cannot be guaranteed. You can crab and fish at this community harbor area.

- SPECIAL NOTE: This rental home has a 5 night minimum during the off season. 

- 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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Lighthouse View

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water Access
Pet Friendly
Pool
Internet

Lighthouse View is located on the east side of our island and includes a private community pool for your enjoyment. The 3 bedroom, 2 bath townhouse features two first floor bedrooms (one with Roku) with full bath in the hallway and a master bedroom suite upstairs. There's water access across the street with a beautiful waterfront lot and dock. Lighthouse View features wireless internet and cable tv (with a premium tier that includes sports, educational, food and other channels).

- 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. 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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Seas the Day

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
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.

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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.

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Sunrise Shore

3 Bedrooms
3 Baths & 1 Half
14 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Pool
Hot Tub
Internet

Spend your precious vacation time at this truly stunning, one-of-a-kind architectural masterpiece! From the moment you walk in the French entry doors, you'll be "wowed" by the floor to ceiling windows and 3-sided glass fireplace. The chef's quality kitchen is brand new with stainless steel appliances and granite counter tops. There are multiple decks for enjoying some relaxing downtime and taking in the unobstructed views of Oyster Bay. Professionally decorated with clean, modern Bohemian-chic decor and furnishings, you'll find yourself surrounded by simple, upscale comfort. There's a 70" TV in the living room, and all the bedrooms feature their own flat-screen TVs and Amazon Echo devices. Stream all of your favorite shows from Hulu, Netflix or Disney+! "Sunrise Shore" is located in one of Chincoteague Island's most popular waterfront residential communities - Oyster Bay I. Conveniently located to Maddox Blvd. (Beach Road) and downtown Chincoteague, yet far enough to escape the hustle & bustle. | | The main level of this home features the main living areas (kitchen, dining room, living room), a powder room, a pool shower bathroom ,and the master bathroom en suite. The upstairs features 2 more bedrooms, both with private balconies, and a full bathroom. There's also an additional loft sleeping area. | | The outdoor areas offer exceptional entertaining and relaxation space. Cool off in the 10' x 40' saltwater in-ground pool, or gaze at the stars as you spend the evening in the 6-person hot tub. Dine al fresco on one of the many decks, all while enjoying the water views. There's plenty of room in the yard for a game of corn hole or catch.

- 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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Serenity at Oyster Bay

3 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water View
Gas Grill
Screened Porch
Internet
Outdoor Shower

Aptly named, "Serenity at Oyster Bay" is just what you'll find at this delightful vacation home. Located in the highly-demanded community of Oyster Bay I, you'll enjoy the peaceful, quiet area nestled amongst the tall pines and marsh grasses. The main living area features a fantastic open floor plan; perfect for gathering the family and entertaining. The back of the house features a bright sunroom that looks out over a natural preserve - cozy up with a cup of coffee and a nice book! This home also features 3 bedrooms, 2 full bathrooms (completely remodeled) and has undergone a lot of fresh new upgrades! There's a little sitting deck out back, a screened porch, covered picnic/game area (with cornhole boards), fish cleaning station, and so much more! And, as if that's not enough, there are water views and you're very close to the Oyster Bay Community water access! Don't delay - Serenity at Oyster Bay is sure to book quickly!

- 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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Dragonfly Point

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

"DRAGONFLY POINT" is a magnificent waterfront property on Oyster Bay & canal. Surrounded by water on three sides of the home, you see the bay and canals from every window! The abundance of decking for entertaining will amaze you with easy access on both floors. Upper family room/loft with unobstructed views. The home has beachy-chic feel with built in bookcases, shiplap, custom fixtures and bathrooms, and more. Two master bedroom suites - upper and lower. Totally fenced in yard that has mature plantings, kayak launch with concrete pad, 120' pier that extends into the bay, comfortable screened porch and much more! Many updates recently including washer & dryer, brand new kitchen & appliances, new bathrooms, etc. SIMPLY BREATH TAKING VIEWS! Come for a stay at Dragonfly Point - it's one you surely will not forget!

- This property has a 7 night minimum stay year 'round. 

- 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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Piney Island Paradise

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Internet

Welcome to Piney Island Paradise! This well-furnished townhouse is nestled in a secluded cul-de-sac along East Side Drive and offers some of the best views of Assateague Island and the historic lighthouse located across the channel. The channel on Eastside offers some of the calmest water for kayaking, plentiful crabbing, and great fishing. Enjoy the most beautiful sunrise views from this vacation home along with quiet solitude! This home also offers 2 kayaks for your enjoyment! 

Upon entering this home, you will find a half bath, first floor bedroom with a queen-sized bed, a well-stocked kitchen, living room, and large waterfront deck with plenty of seating to relax, enjoy the wildlife, and watch the ponies grazing on Assateague Island. On the 2nd floor you will find two more bedrooms as well as the laundry area. The main suite features a king-sized bed with a full bathroom and waterfront deck to enjoy the peaceful sounds of nature and beautiful sunrise views. You will also find a 3rd bedroom that easily accommodates 5 more guests. This room features a twin over twin bunk, a twin over full bunk, and a full bathroom with walk in shower. This home also includes a nice assortment of beach chairs and a small attached garage where you can store your bicycles and kayaks. If you are looking for a home with all the amenities and want to enjoy the beauty of Chincoteague & Assateague Island, this is it!

- 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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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 with an additional fee of $200 per pet. All pets must be disclosed prior to arrival. Pet restriction: limited to two 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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Charlie's Bayside Retreat

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
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 King 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.

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