Chincoteague Vacation Rentals

Chincoteague Island Vacation Rentals

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

Welcome to beautiful Chincoteague Island, also known as Our Little Island by the Sea! 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 183 properties available
Life takes us down many paths, but our favorite ones lead to the Beach. Looking for the perfect Island getaway for your family? Welcome to Bertie Street Cottage - adorable and affordable in the heart of the Island. Located in a peaceful, quiet part of our wonderful Island, you'll enjoy the serenity here after a busy day of exploring Assateague Isla
Hot HOT 16
Bertie Street Cottage
House
$99 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
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 105
The Salty Crab
House Pet Friendly
$103 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 Sonata at Sea Tag Lodge, formerly "Sea Tag #14". These fabulous Condos are located directly on the Assateague Channel with some of the
Hot HOT 16
Sunrise Sonata
Condominium
$68 - $225 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
GORGEOUS updates!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
Hot HOT 14
Assateague Inn 105-S
Condominium
$45 - $329 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Channel View Charmer - Every moment has the potential to be amazing….**Now Dog Friendly!** Channel View Charmer is totally Renovated for 2023 - you're going to love it!Looking for the perfect beach getaway for your family? Channel View Charmer will charm it’s way into your heart forever! This adorable Water View Home has to be in one of the best lo
Hot HOT 13
Channel View Charmer
Cottage Pet Friendly
$90 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 8 guests
Welcome to Safe Harbor on magical Chincoteague Island - the perfect place to relax, rewind, and reconnect. This adorable Dog-Friendly Cottage simply oozes that quintessential Chincoteague Charm you love so much, while giving you the Modern Amenities you need. Located in the heart of our Island at the corner of Chicken City and Ridge, you’re close t
Hot HOT 11
Safe Harbor
Cottage Pet Friendly
$75 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 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 11
East Side Breezes
House
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 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 26
Shackeau East
Cottage
$125 - $325 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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 11
Sunrise Serenade
Condominium
$65 - $200 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Sunset Bay 110 - Relax, Rejuvenate, Reconnect....Sunset Bay 110 is now DOG FRIENDLY with no additional pet fee! Must be pre-approved and max of 2.Welcome to Sunset Bay 110 - Hawk’s Nest - at fabulous Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, a
Hot HOT 21
Sunset Bay Villa 110 - Hawk's Nest
Condominium Pet Friendly
$150 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
At the Beach, life is different. Time doesn't move hour to hour, but with the flow of the Ocean. 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? Now is the time - grab the kids, the dogs, and the horses - that’s right - Seahorse Shanty is Dog AND Horse Friendly! Up to 2 well
Hot HOT 16
Seahorse Shanty
House Pet Friendly
$150 - $559 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Isn't it time for a new romance.....with Life?! A visit to fabulous Bay Pony is certainly the place to begin. This phenomenal End-Unit Townhome is located in a wonderful little community, Silver Sails. One of the most unique and wonderful features of this Neighborhood is that it has a spectacular seasonal Community Swimming Pool for you to enjoy af
Hot HOT 10
Bay Pony
Town House
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

Tell us what you're looking for and someone will contact you with available options.

I agree