25 incredible Vacation Rentals in Chincoteague, VA

Ready for a quiet, serene and nature-filled vacation? Chincoteague Island is located on Virginia’s Eastern Shore and is known for its wild ponies, quiet beaches, and scenic sunsets over Chincoteague Bay.

From ponies, to waterfowl, to sea creatures and so much more, this is the perfect island to sit back, relax and explore via kayak. 

Chincoteague Vacation Rental

Grand Victorian on North Main

Details: Sleeps 10 in 4 bedrooms + 2.5 bathrooms | Rental Info

Located along Main Street, this gorgeous Victorian still has much of its original charm. 

There is an outside hot and cold shower, great for rinsing off after a day at the beach. Additionally, there is an enclosed yard and a dog park nearby. Pets are allowed with an additional fee. 

There is a game room and futon on the third level of the house, so there really is something for everyone at this property. 

Chincoteague Vacation Rental

Rhythm and Blues

Details: Sleeps 7 in 3 bedrooms + 2 bathrooms | Rental Info

This stunning beach oasis features architectural windows and a rustic wood-clad interior. Guests enter through a screened porch but there is also a large front deck to bird watch from. 

There is a huge loft with a wall of windows and a generous area dedicated for the kids. Additionally, there is a shared fire pit with the sister house, Les Bons Temps. If you have a large group, these two properties can house 13 people. 

Guests can easily launch kayaks or small boats from this water front property and fish for crabs from the dock while they’re at it. 

Chincoteague Vacation Rental

Lavinder House

Details: Sleeps 10 in 5 bedrooms + 4 bathrooms | Rental Info

This stunningly unique purple waterfront home is truly one of a kind. With water views from its balconies and most rooms, this charming Victorian-style home honors the traditional interiors from when it was built, complete with original woodwork and a brick kitchen floor. 

This property once belonged to actress Linda Lavin. There is an open front porch and a screened porch, allowing for unobstructed panoramic views of Chincoteague Bay. 

Guests have access to two kayaks, paddles and life jackets. 

Chincoteague Vacation Rental

Duck’s Delight

Details: Sleeps 10 in 4 bedrooms + 2 bathrooms | Rental Info

With three queen sized beds and two sets of bunk beds, this house can accommodate quite a large party. 

The house is located within walking distance to town and positioned along a flat road suited for bike riding. 

Included with the house is an outdoor enclosed shower, beach umbrellas, beach chairs, coolers, a barbeque grill and a clothes line, making this a great beach house to seamlessly move into for vacation. 

Chincoteague Vacation Rental

Captain’s Rest

Details: Sleeps 8 in 3 bedrooms + 3 bathrooms | Rental Info

This brand new luxury townhome is located across the channel from Chincoteague Island on Marsh Island and is known for its impressive sunset views. 

There is a private waterfront balcony perfect for spotting waterfowl. With a spa-like primary bathroom and a walk-in shower with custom tiling, this place is indeed luxurious. 

This property does not rent to groups with guests under 25. 

Chincoteague Vacation Rental

Les Bon Temps

Details: Sleeps 6 in 3 bedrooms + 2 bathrooms  | Rental Info

Located steps from the public boat launch, this property is great for nature lovers and boat lovers. 

Travelling with a large group? Located just next door is its sister property, Rhythm & Blues, together the homes will sleep 13 people. Additionally, there is a shared fire pit between the two houses. 

This property does not rent to groups with guests under 25. 

Chincoteague Vacation Rental

Casas de la Isla

Details: Sleeps 8 in 4 bedrooms + 2 bathrooms | Rental Info

This cute historic home is close to town and features a large front sleeping porch, complete with a daybed and trundle, perfect for enjoying the summer breeze and maximizing space. Additionally, there is an air mattress on site so the property can sleep up to ten guests!

The largest room has a queen bed and gorgeous windows allowing for natural light to stream in, and a seating area. There is a bedroom with single beds, great for the kids. 

Chincoteague Vacation Rental

Chincoteague Channel Townhome

Details: Sleeps 6 in 3 bedrooms + 3 bathrooms | Rental Info

A stunning waterfront townhome, take in views of the Chincoteague Channel. There are balconies overlooking the channel from the living room and the master bedroom, which makes this a great spot to see both sunrise and sunset.  

Guests have the ability to rent a boat slip for an additional $100. Enjoy the sights of Chincoteague and its wildlife from the water!

Chincoteague Vacation Rental

Contemporary Cottage

Details: Sleeps 8 in 3 bedrooms + 3 bathrooms | Rental Info

Nestled in a quiet setting about half a mile from downtown, this unique rental has many opportunities to spot wildlife with its massive front windows. 

There is a newly renovated kitchen complete with a stainless steel double oven, double drawer dishwasher and a five burner gas cooktop. French doors open to a screened in porch. 

There is a cleaning station for fresh catches, a covered garage under the house, and a container of corn for feeding the local wildlife. 

Chincoteague Vacation Rental

Oyster Bay Beach Home

Details: Sleeps 8 in 4 bedrooms + 3.5 bathrooms | Rental Info

This custom beach house has incredible water views overlooking Oyster Bay. Guests can fish and crab from the backyard. 

There are many windows in this unique home and most bedrooms have waterside balconies. 

Interestingly, the bedrooms are on the first level while the main living area is on the second level. For rainy days, the home has four cable TVs. 

Chincoteague Vacation Rental

Island Pearl

Details: Sleeps 6 in 3 bedrooms + 3 bathrooms | Rental Info

Located just a short bike ride from the beach, this property is a great place to relax and unwind. Nearby, there are two fishing marinas on the southern end of the island on Main Street, and two miniature golf courses on Maddox Blvd. 

There is a fabulous screened porch along with two levels of balconies. 

Chincoteague Vacation Rental

Waterman’s Daughter

Details: Sleeps 6 in 3 bedrooms +3 bathrooms | Rental Info

This townhome is located off of East Side Drive and features a lovely second floor balcony with sweeping views and a table for two. 

There is a full kitchen, complete with a stove top oven, microwave, dishwasher, and a kitchen bar with seating for three. 

For the off season, the property features a cozy fireplace and is pet friendly with an additional fee. 

Chincoteague Vacation Rental

Winder Station

Details: Sleeps 8 in 3 bedrooms + 2 bathrooms | Rental Info 

This new waterfront property is perfect for kayakers and water lovers. The property has direct access to the water!

It is tucked off of North Main Street in a private setting. Bring up to two pets for your stay here and enjoy the great outdoor amenities like an outdoor shower and a screened porch. 

There is a separate living room upstairs with a TV, so when travelling with a large group everyone has their own space.

Chincoteague Vacation Rental

A Teague of Our Own

Details: Sleeps 8 in 3 bedrooms + 2 bathrooms | Rental Info

It’s hard to miss this house with its bright blue siding and vibrant red door. Inside, it is decorated in a “beachy-chic” style. The living room comes complete with a flat screen TV and an electric fireplace. 

The kitchen comes fully stocked with a gas stove, sharp knives and a blooming herb garden. 

Outdoors, there is a tiki-shower, a large carport and enough room to hold a cookout in the yard. Pets are allowed with an additional fee. 

Chincoteague Vacation Rental

Unplugged in Chincoteague 

Details: Sleeps 8 in 3 bedrooms + 2 bathrooms | Rental Info 

This house comes stocked with everything your family could need for a fun, active, outdoors vacation. With boogie boards, beach chairs, sand toys, beach umbrellas, a tandem kayak, life jackets, crab box traps, and much more, you’ll find yourself outside exploring the entirety of your stay. 

There is a front enclosed porch, outdoor shower, and two car garage along with a long driveway. For rainy days, the house comes with many books on Chincoteague’s history and board games and puzzles perfect for a family game night. 

This family-run rental has all of the charm of staying at a bed and breakfast.  

Chincoteague Vacation Rental

Pier Home

Details: Sleeps 6 in 3 bedrooms + 2 bathrooms | Rental Info

Nestled along the salt marshes of Chincoteague Bay, this property includes a private pier perfect for launching small boats, crabbing, and fishing. 

There are numerous large windows and oversized sliding glass doors, so the views are panoramic. The first floor is completely wheelchair accessible, providing access to the main living areas and large master bedroom suite. 

This waterfront property is sure to have you relaxed in no time!

Chincoteague Vacation Rental

Laughing Pony

Details: Sleeps 10 in 4 bedrooms + 2 bathrooms | Rental Info

This three story traditional home is located on the edge of town and features many new renovations. It is near the shopping and waterfront downtown plaza. 

The garage comes complete with beach chairs, umbrellas, boogie boards and a charcoal grill. Outside is an outdoor shower and great deck. 

Chincoteague Vacation Rental

Sunset Dreams

Details: Sleeps 8 in 3 bedrooms + 3 bathrooms | Rental Info

A luxury waterfront townhome, this is a premier spot for watching the sunset. The unit features a second floor balcony and water views from most rooms. Additionally, there is an enclosed air-conditioned sunroom. 

Outside, there is an outdoor shower and across the street is a long pier perfect for fishing and crabbing. 

This rental is pet friendly with a two dog maximum and an additional fee. 

Chincoteague Vacation Rental


Details: Sleeps 10 in 4 bedrooms + 2 bathrooms | Rental Info

This custom beach house is located on Willow Street and is decorated with the nautical colors of sea glass, sand and the ocean. 

There is tons of natural light in this property with several skylights, windows and a sunroom. Additionally, there is an outdoor hammock, large patio with a gas grill and picnic table and a gazebo! The outdoor living spaces here are unmatched. 

This is a great house if you have kids as there are two twin bunk beds with trundles. 

Chincoteague Vacation Rental

Endless Summer

Details: Sleeps 8 in 4 bedrooms + 3 bathrooms | Rental Info 

A large white dream house, this property features a sweeping front porch and a freshly updated kitchen. While it was built in the 1930s, it still carries its Chincoteague charm with many modern amenities. 

It is located on the popular East Side, just a short walk from the public boat launch and dock. There is enough parking at the home for guests to tow their boat along, too!

There are three other rentals on this street, making it an ideal spot to rent for big groups. However, this property does not rent to groups under the age of 25 or bachelor and bachelorette parties. 

Chincoteague Vacation Rental

Island Temenos

Details: Sleeps 8 in 5 bedrooms + 1.5 bathrooms | Rental Info

Located on South Main Street near the Historic District for Dining and Shopping and Robert Reed Waterfront Park, you’ll even be able to see the wild ponies at the carnival grounds. 

Filled with charm, this property greets you with a white picket fence and a tree swing. Additionally, there is a screened porch. 

Upstairs is perfect for the kids with two spacious bedrooms with two twin beds in each and a half bathroom to share. 

Chincoteague Vacation Rental

Jay’s Waterside Retreat

Details: Sleeps 6 in 3 bedrooms + 1.5 bathrooms | Rental Info

You will never want to leave this waterside property with its waterside firepit and two open air decks. There is also a screened in porch with a dining set for six guests. 

The property includes two kayaks and four bicycles free to use. Guests can kayak from the private dock to the bay, or catch dinner with the included crab trap and net. It is not far from the community boat launch. 

Pets are welcome to stay with an additional fee, though pets are not allowed on the beach. 

Chincoteague Vacation Rental

Sunset Bay Villas Waterfront Condo

Details: Sleeps 8 in 3 bedrooms + 2 bathrooms  | Rental Info

A gorgeous luxury corner unit, this condo has stunning views of the Intracoastal Waterway, Wallops Island and the Chincoteague Channel. 

There are immense nine foot windows so every room has a view of the water. 

Located just steps from a pool, gym and marina, there are many amenities suitable for a relaxing vacation. 

Chincoteague Vacation Rental


Details: Sleeps 10 in 3 bedrooms + 2 bathrooms | Rental Info

This new home was built in 2019 and features an open floor plan, perfect for two families with kids or three couples or even one large family. It is located just a short walk away from Main Street and the Chincoteague Fair Grounds. 

A large screened in porch provides a great view of sunsets, and the property includes beach chairs, umbrellas and beach toys for use at the nearby beach. 

The property is dog friendly, but does include an extra pet fee. 

Chincoteague Vacation Rental

Piney Island Home

Details: Sleeps 8 in 3 bedrooms + 2 bathrooms | Rental Info

This brightly colored single family home screams beach vacation with its decor. The cottage has been newly renovated and is just minutes away from Assateague’s nature trails and beach.

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