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Shackeau East

1 Bedroom
1 Bath
4 Guests
Chincoteague Island
Piney Island
Waterfront
Screened porch
Internet
Fireplace

Check out the NEW Shackeau East! This charming Piney Island waterfront cottage has some of the most amazing views of Assateague Island and has just been newly renovated! With many upgraded amenities, you will fall in love all over again with this great cot

Hill House

4 Bedrooms
2.5 Baths
9 Guests
Chincoteague Island
In Town
Pet Friendly
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. Hill House features 4 bedrooms an

Windshadow

3 Bedrooms
2.5 Baths
8 Guests
Chincoteague Island
North Main
Waterfront
Pet Friendly
Boat Dock
BBQ Grill
Charcoal Grill
Screened porch
Internet
Fireplace
Outdoor Shower

You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living

Serendipity

3 Bedrooms
1.5 Baths
6 Guests
Chincoteague Island
South Main
BBQ 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 Ch

June's Retreat

4 Bedrooms
5 Baths
10 Guests
Chincoteague Island
North Main
Waterfront
Boat Dock
BBQ Grill
Screened porch
Internet

June’s Retreat is Chincoteague Island’s premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms w

Our Happy Place

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Oyster Bay
Waterfront
Pet Friendly
Boat Dock
BBQ Grill
Screened porch
Internet
Outdoor Shower

Paradise found! Look no further than this fabulous beach retreat that is waiting for you! Tastefully decorated and comfortably furnished, 'Our Happy Place' offers simple, clean and relaxing accommodations for up to 7 guests. You can even bring your 4-legged family member as well (small/medium dogs...

Heron Creek

3 Bedrooms
2.5 Baths
8 Guests
Chincoteague Island
In Town
Water View
Pet Friendly
Gas Grill
Screened porch
Pool
Internet

This beautiful creek front duplex has everything you could dream of in your vacation home. The moment you enter Heron Creek you'll be invited by the high foyer ceilings that will walk you into the spacious great room. There you'll find a beautiful upgraded

Pony Pen

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
South Main
Gas Grill
Screened porch
Internet

Round-up the family and bring them for a memorable vacation at "Pony Pen"! This cute-as-a-button island cottage is located on the southern end of Chincoteague Island, not too far from Captain Bob's Marina, Curtis Merritt Harbor and Memorial (waterfront) Pa

Willaway

3 Bedrooms
2 Baths
10 Guests
Chincoteague Island
South Ridge
Pet Friendly
Gas Grill
Screened porch
Internet

We are excited to offer one of our newest rentals in our inventory, Willaway! Located off of South Ridge, within walking distance of Tom's Cove, this sweet home sits tucked behind mature crepe myrtles situated on a large lot. Tastefully decorated, clean, a

Grandview

4 Bedrooms
4 Baths
10 Guests
Chincoteague Island
North Main
Waterfront
Pet Friendly
Boat Dock
BBQ Grill
Screened porch
Internet
Fireplace
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

Coral Cove

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Oyster Bay
Waterfront
Boat Dock
BBQ Grill
Gas Grill
Screened porch
Internet
Outdoor Shower

We are beyond excited to be able to offer you "Coral Cove" for your next Chincoteague Island vacation - we just KNOW you will love it! Formerly known as "The Fig Tree", Coral Cove has just undergone a complete renovation and has a true "WOW!" factor. On th

Logan's Sunset

3 Bedrooms
2.5 Baths
8 Guests
Chincoteague Island
South Main
Waterfront
Pet Friendly
Charcoal Grill
Screened porch
Internet
Outdoor Shower

Logan's Sunset (formerly known as "Sunset Dreams II") is a great waterfront townhouse on Chincoteague Bay, featuring a waterside master bedroom suite with jetted tub, waterside balcony for you to enjoy beautiful sunsets, a long pier for fishing & cra

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