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.


Popular Chincoteague Island Rentals

House Rentals | Condo Rentals | Waterfront Rentals | Rentals with Pools | Pet Friendly Rentals | Communities


Properties Available 171 properties available
The best things in Life are the people we love, the places we’ve been, and the memories we make along the way…..Life is busy - plain and simple. Work, meetings, schedules, lessons - pretty much chaos - all the time! This makes breaking away from the day to day more important than ever. Pack a bag, grab those who matter most, and get ready to make s
Hot HOT 19
Kindred Tides
House
$125 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Serenity Now -  It's exactly what you need!Welcome to Serenity Now in gorgeous Captain’s Cove - one of the best kept secrets on the Eastern Shore of Virginia! This spectacular Vacation Home will make all your dreams come true with something for everyone in the family. Located directly on the Chincoteague Bay, this home is only 25 short minutes by c
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Serenity Now
House
$250 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Have you always wanted to Vacation on Chincoteague Island, but couldn't bear the thought of 4 of you in a hotel room? Love the idea of a Vacation Home, but don't want to break the bank? Look no further than Sunrise Serenade at Sea Tag Lodge, formerly "Sea Tag # 24". These fabulous Condos are located directly on the Assateague Channel with some of t
Hot HOT 18
Sunrise Serenade
Condominium
$65 - $200 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Sky above, Sand below, Peace within…..Here at Seaside, we believe that finding the “perfect” Vacation Home is so much more than merely finding a place to lay your head at night. We are all about “Experiences” ~ and a stay at ‘East Side Breezes’ is just that ~ a blissful Experience that will be treasured by your family for years to come. This specta
Hot HOT 14
East Side Breezes
House
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Happy Pines has some great updates for 2024 including New Floors throughout and updated Bathrooms!As you turn onto Pine Creek Drive, you will feel the hustle and bustle of the busy world melt away. Happy Pines is located near the end of this quiet street, nestled in a Pine Grove, and surrounded by beautiful trees and Beach Grasses. This lovely 3 Be
Hot HOT 14
Happy Pines
House
$125 - $335 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Changes in Latitude, Changes in Attitude….Jimmy Buffet sure does know what he’s talking about, doesn’t he?! Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch
Hot HOT 25
Sunset Bay Villa 309 - Changes in Latitude
Condominium Pet Friendly
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
So, you'd like to be only minutes from the Beach, close to Shopping and Dining, able to walk to the park that has THE best Sunsets anywhere, and stay in an affordable, yet awesome Vacation Home? You may think that is a tall order for us to fill, but it's not! Welcome to Victoria Cottage on Church Street - This truly delightful 3 Bedroom/ 2.5 Bath V
Hot HOT 14
Victorian Cottage
House
$85 - $265 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
“Travel is the only thing that leaves you speechless, then turns you into a storyteller.” ~ Ibn BattutaHave you been longing for a Vacation Experience that your family won’t soon forget?! Life is so busy - work, school, games, and meetings steal so much precious time from us. It’s so important to grab those who matter most, and just BE together. An
Hot HOT 26
Eventide
House
$125 - $295 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Everyday should be a Beach Day…..When was the last time you had a Vacation that truly took your breath away? Life is so busy - work, school, non-stop commitments, or so it seems. If you’ve been yearning for a getaway that will relax, refresh, and rejuvenate you, clear the calendar, because we have the perfect place for you!Welcome to Duck Harbor at
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Duck Harbor at Waters Edge
Town House
$125 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Flex Stay Home - Captain's Cove doesn't allow Arrivals or Departures on Sundays. A day spent at the Beach is never a wasted day…..Ready for a Vacation that will thrill everyone in your family? You’ve found ‘The Sweets Spot’ right here in Captain’s Cove, for sure! Captain’s Cove Golf and Yacht Club is one of the Best Kept Secrets on the Eastern Shor
Hot HOT 21
The Sweets Spot
House
$135 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
The Baywatch Bungalow - If you’re not barefoot, then you’re overdressed…..Beautiful Updates for 2023!!Close your eyes and feel the salty, sweet bay breeze wash over you. Breathe in the smell of Coppertone - hear the Gulls cry above. This is the very essence of The Baywatch Bungalow in beautiful Captain’s Cove Golf and Yacht Club - one of the Best K
Hot HOT 33
The Baywatch Bungalow
House
$125 - $295 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
**Captain's Rest is now Flex-Stay ALL year long!**We travel not to escape Life, but so that Life doesn't escape us. It's so hard to find time to break away from the daily grind and spend time with those who matter most - but, we all know there's nothing more important. Make time to make Memories, because we've got the place for you! Welcome to Capt
Hot HOT 18
Captains Rest
Town House
$99 - $575 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests

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