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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.

Lighthouse View

3 Bedrooms
2 Baths
8 Guests
East Side
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.

Cockleshell Cottage

3 Bedrooms
3 Baths
10 Guests
Oyster Bay
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.

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.

Heron's Cove On Salt Meadow

4 Bedrooms
5 Baths
12 Guests
In Town
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Internet
Outdoor Shower

Peaceful and stunning waterfront home! Located on a quiet side-street, Heron's Cove features a reverse floor plan with all bedrooms on the first floor, and the main living-level on the second floor. This allows you to capture and maximize the fabulous bay views! The second floor also features a great room with cathedral ceilings, fully equipped kitchen, gas fireplace and screened gazebo. In addition, there's multiple open decks and a shared dock into Little Oyster Bay. There are three bedrooms that each have a king size bed, and one bedroom that has two sets of bunk beds. Each bedroom has a private bath. Luxurious comfort while surrounded by Chincoteague's natural beauty and wildlife! Floor Plan: Downstairs (first level) features 4 bedrooms, all with attached private bathrooms. Two of the downstairs bedrooms and the sitting area have private waterside balconies. Upstairs features an open floor plan with the kitchen, living room and dining area. There is also a full bathroom (shower only) upstairs.

- 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.

Endless Summer

4 Bedrooms
2 Baths
9 Guests
Piney Island
Water Access
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come enjoy your stay at one of the most sought out locations on the Island. Easy, convenient access to the beach- With the large open floor plan, high ceilings, and easy one level living, you have everything you need at Endless Summer. Bring along your furry friends to make your vacation complete! This home has plenty of room for the whole family to gather. Enjoy the nice screened in porch or the large open front porch with your morning coffee and listen to the serene sounds of nature. The Piney Island Community offers convenient access to a kayak launch located on Pine Drive, just minutes from the 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. BREED RESTRICTIONS DO APPLY

- 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.

Blue Marlin

3 Bedrooms
2 Baths & 1 Half
8 Guests
North Main
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Internet

Blue Marlin is a brand new home that is now available exclusively - you will NOT want to miss your opportunity. Visitors from all around fall in love with the charm and beauty of our small town. Blue Marlin is nestled just a few short minutes from the heart of our downtown and offers everything you will need to enjoy a true Island vacation. Spectacular views are abound from just about every room of this gorgeous home. From the time you enter, become enamored with the fresh, beach-like feel of this well thought out Island Home. Blue Marlin offers first floor living, complete with a half bath off of the well-equipped kitchen, a king sized bedroom with beautiful bay views, TV, and en-suite bathroom. Upstairs you will find a spacious sitting entertainment area featuring a sleeper sofa and large TV, as well as two bedrooms. Each bedroom is tastefully decorated and comfortably furnished for a wonderful vacation stay. There are two twin beds, as well as a queen sized bed (with 40 in. TV) upstairs, along with a full bathroom. You may take notice to the many handcrafted furnishings in the home that the owners have taken great pride in creating. Blue Marlin offers front porch sitting, breathtaking sunset views, an outdoor grill, long dock with ladder, (yes, bring your boat!) - there's even extra parking for your boat trailer (behind the yellow house). Everything you need for a perfect vacation is here.. Oh, did we mention this home is pet friendly too?! 

- 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.

Belle of the Bay

4 Bedrooms
2 Baths
8 Guests
Oyster Bay
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

Truly the "Belle of the Bay", this beautiful custom waterfront home is tucked away at the very tip of one of Chincoteague's most popular residential communities - Oyster Bay I. This means you'll enjoy unobstructed 360 degree water and marshland views from nearly every space in the home. The decor and local art collection alone will "wow" you! Watch the sun rise as you sip your morning coffee from the balcony or screened porch. Enjoy the quiet and privacy as you watch the wildlife that surrounds this fabulous property. The main house features 3 bedrooms, 2 full bathrooms, and an additional loft sleeping area (twin trundle bed). The detached garage features another living area/bedroom (2 Twin beds) that is available for guest use (lower level garage is not accessible by guests). NOTE: Living room fireplace is not functional. 

- 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.

Pocahontas

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Nestled in the vibrant heart of Cape Charles, this exquisite one-bedroom condominium represents bayside town living at its most refined. Recently transformed through meticulous renovation, the home seamlessly blends simplistic sophistication with coastal charm to create an atmosphere of understated luxury.

The thoughtfully designed interior showcases an open living space with a fireplace and large TV, sumptuous primary bedroom featuring a king-size bed that promises restful nights after sun-soaked days. Step through the doors onto your private balcony, where panoramic views of downtown and the marina create an ever-changing tableau of maritime activity and small-town vibrancy.

Culinary enthusiasts will appreciate the full kitchen appointed with premium new appliances, inviting both casual meals and ambitious dinner preparations. The custom-tiled bathroom elevates daily routines to spa-like experiences, reflecting the property's commitment to refined comfort.

Location defines true luxury, and this residence delivers magnificently. Mere blocks from the shimmering shores of the Chesapeake Bay, you'll find yourself effortlessly immersed in the coastal lifestyle. The convenience of having Cape Charles' most coveted attractions just steps from your door cannot be overstated—savor artisanal spirits at the local distillery, browse distinctive boutiques and art galleries, indulge in gourmet ice cream, or select from diverse dining options.

For the discerning individual seeking a harmonious blend of tranquility and accessibility, this sanctuary offers a rare opportunity to embrace the quintessential Cape Charles experience.

- 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.

An Unfettered View

2 Bedrooms
2 Baths
8 Guests
In Town
Waterfront
Boat Dock
Gas Grill
Internet
Outdoor Shower

This beautiful 2 bedroom ranch home has a quiet, out-of-the-way location situated on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck. Its perfect for crabbing, kayaking & canoeing! An Unfettered View features all amenities including a private master suite with full bath, central air, all appliances including dishwasher, washer/dryer, wireless internet service and a wonderful family room on the waterside of the home. Tastefully furnished and very accommodating, this is a great vacation spot! An Unfettered View is wheelchair accessible.

- 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.

Channel Lookout

2 Bedrooms
2 Baths
6 Guests
East Side
Water View
Charcoal Grill
Internet

This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run and play, or fish and crab at the waterfront Memorial Park. The first floor is an open room consisting of the kitchen, dining area and living room (with queen sleeper sofa). You'll also find a full bath on this level. The second floor offers a queen bedroom with a private deck that has unlimited views of the Assateague Channel! The second bedroom has two twin beds and you'll find another full bathroom upstairs as well. Come and see for yourself! (Waterfront areas, dock, pier and playground area pictured are public property/Memorial Park.)

- 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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