PRIVATE BEACH on the Chesapeake Bay

- Location: Gwynn
- Guest rating: 10/10 (Exceptional, 150 reviews)
- Price: £3,427 (was £3,705, 7% off), for 7 nights, 1 home, £490 per night, includes taxes & fees

Photo by Kacy Kish
We found 243 holiday rentals — enter your dates for availability
Select from 28 homes, 11 cottages and other holiday rentals in Pine Top to find one that's perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include Wi-Fi and a pool. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.















House
Condo/Apartment
Cabin
Cottage
Villa
Chalet

Premier Host
Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host
Sleeps 6 · 3 bedrooms · 2 bathrooms

Premier Host
Sleeps 4 · 2 bedrooms · 1 bathroom

Premier Host
Sleeps 9 · 2 bedrooms · 2 bathrooms

Sleeps 7 · 3 bedrooms · 2+ bathrooms

Sleeps 11 · 4 bedrooms · 3 bathrooms
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From booking to staying, the whole process is simple and enjoyable
Enjoy full kitchens, pools, gardens and more
More space, more privacy, more amenities — more value
When considering a holiday rental in Pine Top, Virginia, the best area to stay in would be the charming neighbourhood surrounding the local parks and natural attractions. This area not only offers a variety of rental properties, suiting different tastes and budgets, but it also provides easy access to some of the region's top attractions.
One top point of interest nearby is the scenic hiking trails in the surrounding hills, which are great for those who enjoy outdoor activities and wish to immerse themselves in nature. Additionally, the local community centre often hosts events and activities that can provide a glimpse into the vibrant culture of Pine Top.
Staying in this neighbourhood allows visitors to experience the tranquillity of the area while still being close to essential amenities and local eateries. The combination of natural beauty and community spirit makes it an ideal base for exploring all that Pine Top has to offer.
Prices for holiday rentals in Pine Top 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 Pine Top to more spacious homes. To get the best value, book early and take advantage of Vrbo’s free rewards program.
You can find great discounts on house rentals in Pine Top 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.
A long-stay holiday rental in Pine Top is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Vrbo offers a wide selection of holiday rentals in Pine Top with parking available—perfect for families or travellers 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.
Book your Pine Top holiday 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 holiday rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
To find Pine Top holiday 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 makes it easy to book with confidence.
Joining Vrbo as a host opens the door to a global community of travellers 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 cosy cabin or a beach house, 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.
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.
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.
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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.
Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Vrbo's Trip Planner makes organising 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.