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
Life is simple….just add water!The way we live today is crazy - we’re always in a hurry! Work, school, meetings, repeat. It’s so hard to find the time to gather those who mean the most to simply BE together. This is where “Dock Holiday” comes in - this home was made for making family memories together. This spectacular Waterfront Home is Brand New
Hot HOT 33
Dock Holiday
House
$145 - $550 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Sea Breeze - Life’s at ease with an Ocean Breeze…..Close your eyes and imagine breathing in that salty, sweet air - the sound of the Gulls, the Watermen harvesting Oysters - you’re beginning to relax, and you’re not even here yet! This is a feeling deep in your soul - this is Sea Breeze…..Located on Marsh Island, you'll have amazing Views of both B
Hot HOT 14
Sea Breeze
House
$275 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
New Stainless Appliances for 2023!Freedom - it's a State of Mind. The sense of freedom that comes with being on Vacation is like none other. When is the last time you broke away from the day-to-day with those you love? Well, the time is now, and the Vacation Home is magnificent Captain Freeland. This beautiful Canalfront Home is located in prestigi
Hot HOT 13
Captain Freeland
House
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
HUGE UPDATES for 2023 - it's gorgeous!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 ta
Hot HOT 13
Assateague Inn 105-S
Condominium
$45 - $358 / 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 a $100 Pet Fee *PER PET*! 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
Hot HOT 17
Sunset Bay Villa 110 - Hawk's Nest
Condominium Pet Friendly
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
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 Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or w
Hot HOT 38
Sunset Bay Villa 209
Condominium Pet Friendly
$125 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
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
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 110-S
Condominium
$45 - $387 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Ready to kick back and enjoy a little “island time”? ‘Shore Beats Work’! If you’re looking for the perfect Home Base for your next Chincoteague Island Adventure, look no further than ‘Shore Beats Work’ in Eastwinds. Located in the very heart of Chincoteague Island, this lovely Townhome is convenient to everywhere you want to be on our beautiful Isl
Hot HOT 16
Shore Beats Work
Town House
$80 - $285 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Looking for somewhere truly special to spend your Chincoteague Island Family Vacation this year? Look no further, as special doesn't even begin to describe the tranquility and beauty of waterfront Family Tides. This adorable home is located directly on Lewis Creek's deep water, so by all means, bring the boat, kayaks, jet skis, or water toy of choi
Hot HOT 15
Family Tides
House
$135 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
New Expanded Deck and Boardwalk for 2021!You know that favorite song that just stays with you - the one you long to hear again and again? This is the feeling you will get while staying at Rhythm and Blues on beautiful Chincoteague Island. Tucked away on the East Side, this Charming Chalet will steal your heart. Located only steps from the Public Bo
Hot HOT 11
Rhythm & Blues
House
$105 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Welcome to Bliss on the Bay - leave your troubles at the door, you won't be needing them here! This super charming 1 Bedroom/1 Bath Condo will make you feel a million miles away from the real world. Located on Marsh Island, you'll have amazing Views of both Black Narrows Channel and the Chincoteague Channel. Perfect for a Romantic Getaway or a smal
Hot HOT 5
Bliss on the Bay
Condominium
$60 - $265 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests

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