Chincoteague Island Vacation Rentals

Chincoteague Island vacation rental homes on Virginia’s Eastern Shore — Seaside Vacations & Sales

Welcome to beautiful Chincoteague Island! Are you ready for a vacation away from the big city and crowded beach resorts? Search through over 170 Chincoteague Island vacation rentals that offer no high-rises, boardwalks, or traffic jams to interfere with your relaxation. For over 15 years, Seaside Vacations & Sales has offered beautiful house rentals and condo rentals that fit any family size or group gathering, all at the lowest rates on the island.

Seaside Vacations offers a variety of options for your upcoming stay, so you never have to settle. Select from waterfront rentals, rentals with pools, and pet-friendly rentals—because even your furry family members deserve a vacation. We also offer rentals in popular communities like Captain's Cove Golf & Yacht Club, Marsh Island, Piney Island, Pointer Lane, Sunset Bay Villas, and The Assateague Inn.

Come experience the charm and natural beauty of Chincoteague Island, including beloved traditions like the world-famous Pony Swim.

Properties Available 211 properties available
Welcome to Chris' Cottage 1!Tucked away in a peaceful setting just a short stroll from the Sea Shell Motel and the beach, Chris’ Cottages offer the perfect blend of comfort, convenience, and classic Eastern Shore charm. This property features three identical cottage-style units, thoughtfully updated and designed for a relaxing coastal getaway. All
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Cottage
$125 - $215 / 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
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Sunrise Serenade
Condominium
$65 - $200 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Welcome to Seaside Serendipity - where happiness comes in waves.... Looking for the perfect beach getaway for your family? You’ve serendipitously stumbled upon THE place to be on Chincoteague Island. This adorable Water View Home has to be in one of the best locations on our beautiful little island. Located adjacent to ever-popular Veteran’s Memori
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Seaside Serendipity
House
$90 - $398 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Mariner’s Light - a lovingly restored historic home that blends timeless Chincoteague charm with fresh, shabby-chic coastal style. Thoughtfully renovated from top to bottom, this adorable vacation retreat feels both nostalgic and beautifully new—where original character meets breezy modern comfort. Y’all are going to absolutely love this
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Mariner's Light
House
$125 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 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
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Victorian Cottage
House
$119 - $294 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
We travel not to escape Life, but for Life not to escape us…..When was the last time you slowed down - took time to watch the birds dance over the water, or just listen to the breeze rustle the trees? Life is crazy - we know! We’re rushing to work, the kids are rushing to school - and the family pup just wants to tag along for all of it. What you n
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The Mane Escape
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The Mane Escape
House Pet Friendly
$125 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Breezy Corner on our little slice of Heaven, Chincoteague Island. Located at the corner of Willow and Jester, you'll be tucked away in a quiet location in the heart of our Island, yet close to everywhere you want to be. The Attractions of Historic Main Street with so many quaint Shops and Restaurants, Robert Reed Waterfront Park, and the
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House
$90 - $285 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 7 guests
Coastal Crab in Captain’s Cove - Just another day in Paradise…..There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at beautiful Coastal Crab in Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly on the C
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Coastal Crab
House
$150 - $396 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
“To travel in the company of those we love is Home in motion.” ~ UnknownWhen was the last time you stepped away from the day to day to just BE together - to laugh, to play, to explore? With no appointments, no baseball practices, and no zoom calls, there’s nothing but time together, and nothing but incredible memories to be made, right here on Chin
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House Pet Friendly
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Ninety-five feet of private Chincoteague Bay shoreline. That's what's waiting in your backyard at Lookout on Main — along with a dock, a ladder, two kayaks, a canoe, crab pots, and front-row seats to the most spectacular sunsets on the island.Set on South Main Street in one of Chincoteague's most coveted locations, this beautifully renovated 5-bedr
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House
$250 - $885 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Bella's Beach Retreat - Assateague Inn 211 -has had some great updates including new Flooring and a totally new bathroom including shower with grab bars, some new furnishings, and new art! 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 Isl
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Bella's Beach Retreat - Assateague Inn 211
Condominium
$45 - $208 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Welcome to Bayberry - a vacation retreat that’s both adorable and affordable! Tucked in the heart of Chincoteague Island on Ridge Road, this 2 Bedroom end-unit townhome is nestled along a peaceful tidal creek, offering beautiful water views, abundant wildlife, and a true island feel—while still being close to everything Chincoteague has to offer. A
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Town House
$85 - $265 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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Frequently Asked Questions about Chincoteague Island

What is Chincoteague Island known for?

Chincoteague Island is Virginia's only resort island, famous for its wild Chincoteague ponies, the annual Pony Swim, and its gateway access to the Chincoteague National Wildlife Refuge on Assateague Island.

Where is Chincoteague Island located?

Chincoteague Island is located on Virginia's Eastern Shore, easily accessible from major Mid-Atlantic cities. It sits approximately 3.5 hours from Washington D.C., 3 hours from Philadelphia, and 2 hours from Richmond. The island is connected to the mainland by a causeway on Route 175.

When is the best time to visit Chincoteague Island?

Peak season runs from Memorial Day through Labor Day, when warm weather, beach access, and full island activities are available. Spring (March–May) and fall (September–October) offer smaller crowds, lower rental rates, and excellent wildlife viewing. The famous Chincoteague Pony Swim takes place annually on the last Wednesday and Thursday of July — one of the most popular events of the year.

Can I see the wild ponies on Chincoteague Island?

Absolutely — the wild Chincoteague ponies are one of the island's most beloved attractions. They roam freely on Assateague Island within the National Wildlife Refuge, and visitors can spot them along the Wildlife Loop, from boat tours, and during the world-famous Pony Swim each July. The refuge recommends staying at least 40 feet from the ponies at all times.

Is there a fee to access Chincoteague National Wildlife Refuge?

Yes, there is a day use fee to enter the Wildlife Refuge and access the beach at Assateague Island National Seashore.

Are there pet-friendly vacation rentals on Chincoteague Island?

Yes — Seaside Vacations offers a selection of pet-friendly Chincoteague rentals for guests who want to bring their four-legged family members along. Browse our pet-friendly rentals to find the perfect fit for your group.

Is the beach at Assateague Island still open in 2026?

Yes — the recreational beach at Chincoteague National Wildlife Refuge remains open throughout the 2026 season.

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