Piney Island Rentals

Desirable Piney Island is the closest Community to Assateague National Seashore. Ride your bike to the Beach, Dining, Activities, & more! You'll love returning to this tranquil Waterfront Community lined with whispering Pines, which even has its own Kayak Launch area.


Properties Available 12 properties available
Whispering Pines, salty breezes, and chirping Tree Frogs - ahhhh. Can't you just picture yourself here right now? Beach Pines is a delightful Vacation Home located on Piney Island, which the is the closest community to Assateague National Seashore on Chincoteague Island. Wild Ponies, Beach Combing, and one of the most gorgeous beaches in our countr
Hot HOT 8
Beach Pines
House
$90 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Island Sage on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. This cozy Vacation Home is just that - a HOME, not just a place to lay your head at night. Located in popular Piney Island, which happens to be the closest community to Assateague National Seashore, you will lo
Hot HOT 20
Island Sage
House
$90 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Stop for a moment and imagine your dream vacation - what would it be like? A spectacular Custom Home perched on the Assateague Channel with breathtaking Views? Or maybe a Dream Home in which everyone has a Master Bedroom with Waterfront Balcony and Private Master Bath? How about a warm and inviting Great Room where you can gather with those who mat
Hot HOT 35
Stoney Point
House
$600 - $900 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Sand Dollars wash upon the shore like smiles from the Sea…..The things we treasure most in this life aren’t ‘things’ at all - time with those we love, precious memories made by the seashore - the most valuable treasure to be had. Welcome to Sand Dollar on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with tho
Hot HOT 28
Sand Dollar
House
$135 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Take a Vacation that makes you forget to check your cell phone….Looking to leave the real world behind - just for a few days? Grab those who matter most, and clear your calendar - Caribbean Ketch is waiting for you! This charming home is located in the ever-popular Piney Island, which happens to be the closest community to Assateague National Seash
Hot HOT 17
Caribbean Ketch
House
$125 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
The Happy Crab - Where dreams are made of Sun and Sand…..There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague I
Hot HOT 26
The Happy Crab
Town House
$120 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Please note - All Decked Out has a Strict Occupancy of 8 at ALL times in the home and on the grounds, and this is enforced. At the Beach, life is different. Time doesn't move hour to hour, but mood to moment. We live by the currents, plan by the tides, and follow the sun. When is the last time you can say you had a day like this? Well, now is the t
Hot HOT 30
All Decked Out
House
$400 - $900 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Slack Tide rents Sunday to Sunday during the Peak Season. Huge Updates for 2024 - New Flooring, Fresh Paint, New Couples Shower, and lots of New Furnishings and Fresh Decor!Slack Tide - by its very definition is a time when the water is completely unstressed. This is a short period of time, kind of like your vacation, but such an important time.  W
Hot HOT 23
Slack Tide
House Pet Friendly
$135 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Live your Life by a compass, not a clock…..**BIG UPDATES for Summer 2023! Both Full Baths Newly Renovated with a Brand New Tub/Shower Combo, New Flooring, and New Kitchen Island!Work, school, traffic, homework, repeat - right?! It’s time for a break - a Beach Break, that is! Get ready to relax, unwind, and simply….be. Be with those who matter most
Hot HOT 23
Happy Hideaway
House
$85 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
**Teague Time has a Brand New Fenced Yard for your Furbaby!**The best things in Life are the people we love, the places we've been, and the Memories we've made along the way. Welcome to Teague Time on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. This beyond-adorable Vacation Cotta
Hot HOT 16
Teague Time
House Pet Friendly
$85 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Just give me the Sea, and a little Cottage just to be…..One of Chincoteague’s most beloved Vacation Homes, Shackeau East, is now part of our Seaside Vacations’ Family! Resting by the water’s edge in ever-popular Piney Island, this adorable Cottage has quite the following! Piney Island is the closest community to Assateague National Seashore, where
Hot HOT 32
Shackeau East
Cottage
$105 - $325 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the whole family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague Island to make Memories that you'll treasure forever
Hot HOT 29
Island Haven
Town House Pet Friendly
$109 - $385 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

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