71 Chincoteague Holiday Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Chincoteague holiday rentals from 5 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $51 to $568 a night.

Information about Chincoteague

About Chincoteague

On Virginia’s Eastern Shore lies the island of Chincoteague, gateway to the famous Assateague Island National Seashore and home to a tight-knit community with a rich history in the seafood industry. Chincoteague is a mere 4 hours from Washington D.C. and Philadelphia, yet the idyllic, quiet island feels like worlds away.

Chincoteague gained fame after the 1961 film Misty of Chincoteague, which highlighted one of its most well-known attractions, its wild ponies. To this day, Assateague Island hosts a herd of approximately 150 wild horses managed by the Chincoteague Volunteer Fire Company. While their origins are debated, many contest that the now aptly named “Chincoteague Pony” is a descendant of survivors of a Spanish shipwreck in the 1700’s.

Things to do in Chincoteague

Made famous by Misty of Chincoteague, the Chincoteague Island Pony Swim has been an annual event in Chincoteague since 1924. Held every July, “Saltwater Cowboys” round up the ponies to corrals for public viewing, and days later proceed to swim the ponies from Assateague Island to Chincoteague for a foal auction, which helps control the population and fundraise for the local Volunteer Fire Company. Visitors can book charter boats well in advance to witness this unique event up close, and each night also includes a carnival celebration, free to the public. The town also boasts a blueberry festival and farmers’ market that weekend for all to enjoy.

Even if you can’t manage to book a charter boat for the Pony Swim, there are plenty of opportunities to embark on guided boat tours and experience the abundant wildlife and unique ecosystem of Chincoteague and Assateague. There are over 15 boat tour companies in the area, and so much coastline to explore. If self-powered boats are more your style, you can rent a kayak on your own or join a Kayak Eco Tour to navigate the islands.

Sure, the beaches here are great, but in an area so rich with natural and cultural history, there’s also so much to learn! Take a trip to the Chincoteague Bay Field Station to participate in a hands-on Atlantic marine life workshop or family camp, or gawk at the North American River Otter exhibit at the Delmarva Discovery Center and Museum. If you can’t make it in July for the Pony Swim, you can still see (and even ride!) real Chincoteague Ponies at the Chincoteague Pony Centre. To discover more about Chincoteague’s vibrant past, trace its history at the Museum of Chincoteague Island for just $4.

Immerse yourself in Chincoteague’s unique maritime culture by trying your hand at clamming or crabbing. After grabbing your supplies at a local store such as Captain Steve’s Bait and Tackle, head over to Swan Cove or along Beach Road in Chincoteague National Wildlife Refuge, where anyone is allowed one bushel of blue crabs per day—that is, if you can catch them! In Toms Cove, bring a bucket and dig for all types of different clams, up to 250 per day. If you’re not that lucky, check out the Oyster Festival in October, or Seafood Festival in May.

Day Trips from Chincoteague

Just about an hour north from Chincoteague is Ocean City, Maryland, a buzzing seaside center with 10 miles of beachfront at your fingertips. Check out the shops, amusement rides, and endless entertainment along its 3 mile-long boardwalk. Ocean City’s high energy environment provides the perfect contrast to the relaxed, small town vibes of Chincoteague, ensuring a fun, well-balanced vacation.

Inland from Ocean City is the largest city in Maryland’s Eastern Shore region, Salisbury. Grab dinner at one of the many area restaurants, see popular artists such as Chris Young at the Wicomico Civic Center, or stroll the art galleries downtown and ride the weekend Trolley down Main Street.

Chincoteague Accommodations

Tripping.com presents a wide variety of accommodations in Chincoteague Island, and since the town is only 7 miles long, you’re always close to anything you’d need! Check out places around Main Street to be near historic downtown—otherwise, Maddox Boulevard is a good bet if you’d rather be close to the beach.

Transportation in Chincoteague

To get to Chincoteague, visitors can fly into Wicomico Regional Airport in Salisbury, or to one of the 6 national and international airports, all less than 4 hours away. After you’ve arrived, the Pony Express will take you to most points of interest around the island for a mere 25 cents.

Vacation Rentals in Chincoteague

Looking for the perfect vacation rental for your Chincoteague getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Chincoteague offers 71 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 53 properties with high-speed internet, 24 full with jacuzzi and pool, and homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $25 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Chincoteague has 71 gorgeous homes with 14 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

Search properties from 5 rental sites in Chincoteague where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 35 HomeAway rentals, 17 TripAdvisor short term rentals and 9 Booking.com vacation rentals.