Photo by Kacy Kish

Pine Top holiday rentals

We found 245 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.

Holiday rentals with weekly discounts – Pine Top

Showing deals for:25 Dec - 1 Jan

Property grounds
Property grounds
Kitchen
Bedroom 6 with queen and one twin and full bath
Exceptional
(98 reviews)

'Pop Castle' Historic Gem on the Rappahannock River

White Stone

9% off
AU$21,782
for 7 nights, 1 home
AU$3,112 per night
includes taxes & fees
'Pop Castle' Historic Gem on the Rappahannock River
Exterior
Property grounds
Beach
Dining
Exceptional
(150 reviews)

PRIVATE BEACH on the Chesapeake Bay

Gwynn

8% off
AU$6,231
for 7 nights, 1 home
AU$890 per night
includes taxes & fees
PRIVATE BEACH on the Chesapeake Bay
Property grounds
Interior
Living area
Interior
Exceptional
(31 reviews)

Charming Spacious Cottage, private, water views, close to amenities

White Stone

8% off
AU$3,390
for 7 nights, 1 cottage
AU$484 per night
includes taxes & fees
Charming Spacious Cottage, private, water views, close to amenities
Exterior
Property grounds
Room
Interior
Exceptional
(124 reviews)

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Gloucester

15% off
AU$1,594
for 7 nights, 1 room
AU$228 per night
includes taxes & fees
Charming Quiet Retreat on North River in Historic Gloucester, Virginia
Marina
Outdoor dining
Private kitchen
Living area
Exceptional
(76 reviews)

Enjoy family fun and Sunsets at Piankatank Point.

Saluda

8% off
AU$3,877
for 7 nights, 1 home
AU$554 per night
includes taxes & fees
Enjoy family fun and Sunsets at Piankatank Point.
Large open concept - perfect for entertaining!
Bahamas? in White Stone
Interior
Master bed with sofa and views of Chesapeake Bay
Excellent
(20 reviews)

BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock

White Stone

10% off
AU$5,402
for 7 nights, 1 home
AU$772 per night
includes taxes & fees
BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock
Interior
Interior
Interior
Property grounds
Exceptional
(11 reviews)

Beautiful Gwynn’s Island Waterfront Home

Gwynn

8% off
AU$3,990
for 7 nights, 1 home
AU$570 per night
includes taxes & fees
Beautiful Gwynn’s Island Waterfront Home
Dining
Living area
Room
Living area
Exceptional
(7 reviews)

Charming Pet Friendly 4-bedroom river view home with grill, in lovely Weems!

Weems

8% off
AU$2,348
for 7 nights, 1 home
AU$335 per night
includes taxes & fees
Charming Pet Friendly 4-bedroom river view home with grill, in lovely Weems!
Interior
Exterior detail
Interior
Property grounds
Exceptional
(47 reviews)

Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!

Gwynn

8% off
AU$3,293
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!
Interior
Interior
Dining
Living area
Exceptional
(21 reviews)

Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home

Gwynn

8% off
AU$4,919
for 7 nights, 1 home
AU$703 per night
includes taxes & fees
Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home
Interior
Exterior
Marina
Interior
Exceptional
(46 reviews)

Waterfront-Peaceful-Weems-VA-NNK-Kayaks-Views

Weems

8% off
AU$2,385
for 7 nights, 1 home
AU$341 per night
includes taxes & fees
Waterfront-Peaceful-Weems-VA-NNK-Kayaks-Views

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Pine Top getaway

Learn about the unique charm of Pine Top with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Pine Top

Do you want to find attractions to visit in the area? Venture out of your cosy holiday rental and experience everything that makes Pine Top a fun spot to go on holiday. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Golden Eagle Golf Club (8.5 mi / 13.7 km)
  • Compass Entertainment Complex (9.1 mi / 14.6 km)
  • Piankatank River Golf Club (3.8 mi / 6 km)
  • Good Luck Cellars (12.6 mi / 20.4 km)
  • Gloucester Golf Club (12.8 mi / 20.6 km)

Exploring the natural features in Pine Top

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Pine Top is a great place to get outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • White Stone Beach (5 mi / 8.1 km)
  • Urbanna Historic District (10.4 mi / 16.7 km)
  • Bethel Beach Natural Area Preserve (13.5 mi / 21.7 km)
  • Hughlett Point Natural Area (13.6 mi / 21.9 km)
  • Chesapeake Bay (17.1 mi / 27.5 km)
  • Fossil Beach (19 mi / 30.5 km)

How to get to and around Pine Top

The nearest airport is in Newport News, VA (PHF-Newport News - Williamsburg Intl.), located 29.8 mi (47.9 km) from the city centre.

Frequently asked questions

What is the best area to stay in Pine Top when booking a holiday rental?
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.
Are all fees included in the Pine Top holiday homes prices shown on Stayz?
Stayz 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.
Are there any Pine Top holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Pine Top holiday homes?
You can find great discounts on holiday homes in Pine Top on Stayz, 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.
Can I change or cancel my Pine Top holiday home booking on Stayz?
To find Pine Top holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pine Top?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Pine Top holiday home?
Book your Pine Top holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pine Top?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pine Top to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.