Chincoteague Vacation Rentals

Chincoteague Island Vacation Rentals

Browse over 150 Chincoteague Island Rentals, all at the Best Rates

Welcome to beautiful Chincoteague Island! Are you ready for a vacation away from the big city and crowded beach resorts? A Chincoteague Vacation Rental means that there are no high-rises, boardwalks, or traffic jams to interfere with your relaxation. We offer beautiful rentals to fit any family size or group gathering, all at the lowest rates around. Come see the wonder of Chincoteague Island, include famous events such as the Pony Swim!

Seaside Vacations offers so many wonderful vacation house rentals from Chincoteague Island to the Mainland. Select from our large choice of Chincoteague Waterfront Vacation Rentals or Rentals with Pools.



Properties Available 180 properties available
Wonderview 208 ~ Take the Journey to enjoy the View…..Life gets busy - work, kids, appointments, pets - it never seems to stop. This makes it more important than ever to take time to stop and smell the roses - or more appropriately, the salty, sweet sea breeze. If you can make the time, we most definitely have the place….Welcome to fabulous Wonderv
Hot HOT 14
Wonderview 208
Condominium
$100 - $375 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Lighthouse Overlook - Every day should be a Beach Day…..Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Lighthouse Overlook was made
Hot HOT 31
Lighthouse Overlook
House
$125 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Ready to have a ‘Shell of a Time’ on your next trip to our Little Island by the Sea?! You will absolutely fall in love with this beautiful Cottage on Chincoteague Island - tucked on a quiet street, but close to everywhere you want to be! Shell of a Time has all that you love about a quintessential Chincoteague Cottage, plus the Modern Amenities you
Hot HOT 19
Shell of a Time
House
$95 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
There’s only one thing more precious than our time, and that is who we spend it on. Even in today’s world, it isn’t always easy to find true quality time with those who matter most. There are Zoom meetings and virtual lessons - the days are still demanding, and perhaps even more stressful than ever. Making that special time for nothing more than ‘t
Hot HOT 17
Hudson House
House
$150 - $500 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
Hot HOT 13
Assateague Inn 204-S
Condominium
$45 - $300 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Live your Life by a compass, not a clock…..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 - giggle, frolic on the Beach,
Hot HOT 22
Happy Hideaway
House
$85 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Pony Swim Crossing - Chincoteague Island is calling…..**PIER AND BOAT SLIP NOT CURRENTLY AVAILABLE DUE TO REPAIRS**“To sit in silence at the shore, watch the waves and hear the surf, is to appreciate the very breath and heartbeat of the earth.” ~ UnknownIsn’t it time to break away from the daily grind? The stress, the traffic, and oh, “schedules” -
Hot HOT 15
Pony Swim Crossing
Town House
$99 - $313 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 5 guests
Island Sunset - “Every Sunset brings the promise of a new dawn.” ~ Ralph Waldo EmersonAnd we cannot think of a better place to begin this new dawn than at Newly Renovated ‘Island Sunset’ on beautiful Chincoteague Island. This one-of-a-kind home not only sits on South Main Street - home of THE most spectacular Sunsets - it features a Private Pier an
Hot HOT 22
Island Sunset
House
$125 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Life’s at ease with a bay breeze…..Do you yearn to be so close to the water that you can take in that salty, sweet sea breeze while you sleep? Imagine fishing and crabbing only steps from your house - or having your Boat docked just behind the house - all the joys of living at the Water’s Edge.Welcome to Water’s Edge in the heart of Chincoteague Is
Hot HOT 23
Water's Edge
Town House
$100 - $350 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Life is good - but Island Life is better!Welcome to The Salty Crab in the very heart of Chincoteague Island! This gorgeous Brand New Home is nestled on Church Street, just a short stroll from our famous Farmers Market and Downtown Historic Main Street’s many Shops and Restaurants. Robert Reed Waterfront Park is also only steps away and home of the
Hot HOT 74
The Salty Crab
House Pet Friendly
$99 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
Hot HOT 12
Assateague Inn 205-S
Condominium
$45 - $311 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Blue Heron - A Breathtaking Eastern Shore Vacation Experience!The most treasured heirlooms are the sweet memories of Family......Blue Heron is located in Eagle's Sound Estates, only 10 minutes from wonderful Chincoteague Island, Home of the Famous Wild Ponies and Misty of Chincoteague, yet you will feel as if you are in your own private Paradise. T
Hot HOT 27
Blue Heron
House
$175 - $300 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests

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