Piney Island vacation rentals

We found 141 vacation rentals — enter your dates for availability

Discover a selection of 54 homes, 12 villas, and vacation rentals in Piney Island that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Piney Island

Why visit Piney Island

  • Outdoor Adventures: Piney Island offers a variety of activities like kayaking and beach outings, perfect for nature enthusiasts.
  • Stunning Natural Beauty: Enjoy the picturesque landscapes and serene waters surrounding the island, ideal for relaxation.
  • Family-Friendly Atmosphere: The island provides a welcoming environment for families, ensuring fun for all ages.
  • Charming Accommodations: Choose from cozy vacation homes and inviting cottages for a comfortable stay.
  • Friendly Locals: Experience the warmth of the community, adding to the charm of your visit.

Popular types of accommodation around Piney Island

Planning your getaway to Piney Island? Discover the charm of this beautiful destination with our top vacation rentals. From cozy houses and inviting cottages to modern condos, there's something for everyone. Consider staying at the Chincoteague Resort for a touch of luxury or the Happy Hideaway for a more intimate experience. Explore your options and make your trip to Piney Island unforgettable.

  • Houses: The top choice for visitors, these spacious homes offer the comfort and privacy ideal for families and groups.
  • Cottages: A delightful option for a cozy stay, these charming abodes provide a quaint atmosphere perfect for relaxation.
  • Condos: These modern accommodations offer great amenities and are conveniently located for easy access to local attractions.
  • Cabins: Perfect for nature enthusiasts, these rustic retreats provide a peaceful escape surrounded by the beauty of the outdoors.
  • Apartments: A practical choice for solo travelers or couples, offering a comfortable stay with essential amenities.**

Top attractions near Piney Island

Piney Island in Chincoteague, Virginia, is perfect for outdoor and beach vacations, offering a variety of attractions like the beautiful island and nearby reserves. Whether you're seeking adventure or a family-friendly experience, you'll find plenty to explore, including Piney Island and Piney Creek. Enjoy the natural beauty and recreational activities that make this destination a must-visit for travelers looking to unwind and connect with nature.

  • Chincoteague National Wildlife Refuge: A serene reserve known for its diverse ecosystems and wildlife, including the famous wild ponies. Enjoy miles of picturesque trails and pristine beaches, perfect for birdwatching and photography.
  • Assateague Lighthouse: This historic lighthouse offers a glimpse into maritime history and stunning views from the top. Its cultural significance and charming surroundings make it a must-visit for history buffs and photographers.
  • Assateague Point: A vibrant town neighborhood that captures the essence of coastal living. Explore local shops and eateries while enjoying the lively atmosphere and beautiful waterfront views.

Things to do recommended for couples

Planning a romantic getaway at Piney Island? Don't miss a visit to Bloxom Winery, just 17 miles away. Enjoy the enchanting atmosphere and entertainment vibes as you sip on exquisite wines, creating unforgettable memories together.

Things to do recommended for families

Families visiting Piney Island can have a splash-tastic time at Maui Jack's Waterpark, where thrilling slides and relaxing pools create unforgettable memories. Enjoy a day filled with adventure and family fun in this vibrant waterpark, perfect for all ages.

Things to do recommended for groups

Groups visiting Piney Island can enjoy a round of golf at Nassawango Golf Course, located 16 miles away, or Captain's Cove Golf and Yacht Club, just 6 miles away. Both venues offer a fantastic outdoor atmosphere perfect for sports enthusiasts.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Piney Island

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Piney Island with a group: Think about how many bedrooms you'll require, along with additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Piney Island with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, as well as look for age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Piney Island: For many families, a trip isn’t truly special without their furry companions. If you relate to this, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Piney Island: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search to enhance your experience.

Where to stay near Piney Island

Piney Island offers a delightful escape for those seeking outdoor adventures and beach vacations. Nestled near Chincoteague Island, visitors can enjoy family-friendly atmospheres and relaxing seaside experiences. Explore charming vacation homes surrounded by ponderosa pines, where friendly locals enhance your stay. Whether you're kayaking through serene waters or soaking up the sun on sandy shores, Piney Island and its nearby attractions promise unforgettable memories for all ages.

  • Chincoteague: Chincoteague is a charming island city that serves as the gateway to Piney Island. Known for its stunning beaches and family-friendly atmosphere, Chincoteague offers a plethora of outdoor activities. Travelers can stroll along the picturesque boardwalk, explore the recreational areas, or indulge in shopping at local boutiques. The nearby landmarks, including the pristine family beach and the scenic esplanade, make it an ideal destination for those seeking relaxation and adventure alike. Whether you're visiting for a day or an extended stay, Chincoteague promises a memorable experience.
  • Deep Hole: Deep Hole is a quaint village located just a mile from Piney Island, making it an easy and delightful addition to your travel itinerary. Known for its outdoor adventures and beautiful beach access, visitors can enjoy activities such as kayaking, fishing, or simply unwinding by the shore. The village features a lovely boardwalk and recreational areas that allow you to connect with nature. With its welcoming atmosphere and proximity to the family beach and local neighborhoods, Deep Hole is perfect for those looking to immerse themselves in the coastal lifestyle.
  • Assateague Island: Assateague Island, located 11 miles from Piney Island, is a stunning natural destination renowned for its breathtaking landscapes and abundant wildlife. This barrier island is perfect for outdoor enthusiasts, offering countless opportunities for adventure, including hiking, birdwatching, and beachcombing. The island is home to the famous Assateague Island National Seashore, where visitors can explore scenic trails, enjoy family-friendly beaches, and witness the iconic wild ponies. With its enchanting scenery and diverse recreational options, Assateague Island is a must-visit for families and adventurers alike.

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? Being open to adjusting your travel dates can lead to significant savings, as prices tend to vary. Additionally, opting for a longer stay often results in even greater discounts. To discover the perfect Vrbo property that fits your budget, utilize our filters to narrow down options by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer truly has its benefits. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on eligible stays. Sign up today and begin earning rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a simple and organized way to plan your travels, whether you’re starting a new trip, resuming an existing one, or managing your itinerary. You can easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, just head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Piney Island?
In Piney Island, vacation houses are the most popular type of rental, with about 52 available across the island. These properties typically offer spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor areas for relaxation. Travelers can enjoy the serene surroundings while having the comforts of home. Additionally, there are around 10 villas that provide a more luxurious experience, often featuring upscale furnishings and private outdoor spaces. Several cottages are also available, offering a charming and cozy atmosphere, ideal for smaller groups or couples seeking a peaceful getaway.
Are there any beach house rentals in Piney Island?
In Piney Island, there are about 36 beach house vacation rentals available, offering a range of options for travelers seeking a coastal getaway. These rentals are typically located near the waterfront, providing easy access to the beach and stunning views of the surrounding area. Most beach houses are equipped with amenities such as fully furnished kitchens, spacious living areas, and outdoor decks or patios ideal for enjoying the sunset. Many properties also feature multiple bedrooms, making them suitable for families or groups looking for an enjoyable stay by the sea.
How much does it cost to rent a vacation home in Piney Island?
Prices for vacation rentals in Piney Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Piney Island to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Piney Island vacation house rentals?
You can find great discounts on house rentals in Piney Island on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Piney Island?
In Piney Island, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature coffee and tea makers for those who enjoy a warm beverage in the morning. Additionally, rentals often come with outdoor spaces such as decks or patios, providing a superb spot to relax and take in the natural surroundings. Onsite parking is typically available, making it convenient for travelers with vehicles. Some rentals also include porches or lanais, enhancing the outdoor experience and offering a cozy area to unwind after a day of exploration.
Can I find family house rentals in Piney Island?
In Piney Island, Virginia, there are numerous family-friendly house rentals available, with around 46 options to choose from. This charming area provides an inviting space for families, with properties often featuring spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces great for children to play. Many homes come with amenities such as air conditioning and Wi-Fi, ensuring a comfortable stay.

Visitors can enjoy nearby attractions, including beautiful waterfront areas and scenic parks, providing great spots for picnics and outdoor activities. The location also offers opportunities for fishing, boating, and exploring the natural beauty of the Virginia coast.
Can I rent a vacation home with a pool or hot tub in Piney Island?
In Piney Island, Virginia, travelers can find a selection of vacation homes available for rent that feature pools and hot tubs, with around 12 properties offering pools and several more equipped with hot tubs. This peaceful destination provides a serene atmosphere for relaxation and leisure. Many of these rentals come with spacious outdoor areas, superb for enjoying the Virginia sunshine, and may include amenities such as fully equipped kitchens and cozy living spaces for family gatherings.
Are there any Piney Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Piney Island with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly vacation rentals in Piney Island?
Yes, you can book pet-friendly vacation rentals in Piney Island, Virginia. There are several options available, with around 13 vacation rentals suiting travelers with pets. These properties typically offer amenities such as fenced yards, pet-friendly furnishings, and spacious living areas, making them suitable for families or groups traveling with their furry companions.

Piney Island is known for its beautiful natural surroundings, and many rentals provide easy access to local parks and outdoor spaces where pets can enjoy walking or playing. The area also features nearby beaches and waterfront activities, allowing for a fun-filled vacation experience for both you and your pets.
Can I find long-stay vacation rentals in Piney Island?
A long-stay vacation rental in Piney Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Piney Island for a vacation rental?
The best time to visit Piney Island for a vacation rental is during the peak season from June to August, with July being particularly popular. This vibrant summer period draws travelers eager to soak up the sun, enjoy water activities, and explore the island's stunning natural beauty.

During these months, temperatures typically range from the mid-70s to mid-80s Fahrenheit, creating ideal conditions for outdoor adventures like kayaking, fishing, and beachcombing. The warm weather also invites visitors to take leisurely strolls along the picturesque coastline and partake in local events, making it a bustling time filled with opportunities for fun and relaxation.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter atmosphere, great for those who enjoy a more peaceful escape while still experiencing the charm of Piney Island. The fall season brings beautiful landscapes and a chance to savor the tranquility of nature, making it a delightful time to unwind.
Are there any remote work vacation rentals in Piney Island?
In Piney Island, Virginia, there are numerous vacation rentals suitable for remote work, with around 50 options available. These rentals often feature essential amenities for productivity, including free Wi-Fi, designated workspaces with desks and chairs, and comfortable living areas conducive to working from home. Many properties also provide a peaceful environment, allowing for focused work sessions while being surrounded by the natural beauty of the area. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Piney Island vacation rental?
Book your Piney Island vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Piney Island, Virginia, United States of America?
Piney Island, Virginia, is a unique destination offering various attractions, particularly for nature lovers and those interested in maritime activities. The island is surrounded by water, making it an excellent spot for fishing, boating, and kayaking. Visitors can explore the beautiful marshlands and coastal ecosystems, superb for birdwatching and observing local wildlife.

Nearby, the historic town of Cape Charles offers charming shops, restaurants, and a lovely beach along the Chesapeake Bay. The Cape Charles Beach is a popular spot for both relaxation and water activities, providing a picturesque setting for visitors.

For those interested in history, the nearby Eastern Shore of Virginia National Wildlife Refuge is not only a great place for outdoor activities but also offers interpretive trails that highlight the area's natural and historical significance.
Can I change or cancel my Piney Island home rental booking on Vrbo?
To find Piney Island vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Piney Island vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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