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:1 Jan - 8 Jan

Property grounds
Property grounds
Beach
Exterior
Exceptional
(150 reviews)

PRIVATE BEACH on the Chesapeake Bay

Gwynn

8% off
S$5,407
for 7 nights, 1 home
S$772 per night
includes taxes & fees
PRIVATE BEACH on the Chesapeake Bay
Property grounds
Interior
Interior
Living area
Exceptional
(31 reviews)

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

White Stone

8% off
S$2,551
for 7 nights, 1 cottage
S$364 per night
includes taxes & fees
Charming Spacious Cottage, private, water views, close to amenities
Room
Property grounds
Living area
Interior
Exceptional
(124 reviews)

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Gloucester

16% off
S$1,368
for 7 nights, 1 room
S$195 per night
includes taxes & fees
Charming Quiet Retreat on North River in Historic Gloucester, Virginia
Private kitchen
Outdoor dining
Marina
Marina
Exceptional
(76 reviews)

Enjoy family fun and Sunsets at Piankatank Point.

Saluda

8% off
S$3,406
for 7 nights, 1 home
S$487 per night
includes taxes & fees
Enjoy family fun and Sunsets at Piankatank Point.
Master bed with sofa and views of Chesapeake Bay
Bahamas? in White Stone
Interior
Large open concept - perfect for entertaining!
Excellent
(20 reviews)

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

White Stone

10% off
S$4,745
for 7 nights, 1 home
S$678 per night
includes taxes & fees
BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock
Interior
Interior
Private kitchen
Property grounds
Exceptional
(11 reviews)

Beautiful Gwynn’s Island Waterfront Home

Gwynn

8% off
S$3,437
for 7 nights, 1 home
S$491 per night
includes taxes & fees
Beautiful Gwynn’s Island Waterfront Home
Interior
Exterior detail
Property grounds
Interior
Exceptional
(47 reviews)

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

Gwynn

8% off
S$2,837
for 7 nights, 1 home
S$405 per night
includes taxes & fees
Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!
Dining
Living area
Living area
Terrace/patio
Exceptional
(7 reviews)

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

Weems

8% off
S$2,011
for 7 nights, 1 home
S$287 per night
includes taxes & fees
Charming Pet Friendly 4-bedroom river view home with grill, in lovely Weems!
Marina
Exterior
Interior
Outdoor dining
Exceptional
(46 reviews)

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

Weems

8% off
S$2,074
for 7 nights, 1 home
S$296 per night
includes taxes & fees
Waterfront-Peaceful-Weems-VA-NNK-Kayaks-Views
Interior
Interior
Interior
Dining
Exceptional
(21 reviews)

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

Gwynn

8% off
S$4,237
for 7 nights, 1 home
S$605 per night
includes taxes & fees
Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home
The narrow and steep original stairs help retain the cottage feel.
Dining area looking into kitchen.
Hall opens up into the porch, dining room and living room.
Perfect desk niche for working. ( if you must...)
Exceptional
(25 reviews)

1891 Coastal Charmer: fully renovated farmhouse

White Stone

8% off
S$1,830
for 7 nights, 1 home
S$261 per night
includes taxes & fees
1891 Coastal Charmer: fully renovated farmhouse

  • 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 most popular type of holiday rental accommodation in Pine Top?
According to our data, houses are the most in-demand holiday property type in Pine Top. But as you know, everyone's idea of an epic trip can differ. Vrbo has holiday homes in a variety of shapes and sizes, and we'll help you discover the perfect fit for you.
How much does it cost to rent a holiday rental in Pine Top?
Property type, season and length of stay are some factors that can affect the price of a holiday home. Simply enter your dates of travel to find your ideal escape. From cosy cabins to plush villas, all Vrbo holiday rentals offer amazing value.
How much does it cost to rent a beach house in Pine Top?
Prices for beach houses in Pine Top will vary depending on the size and style of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and how many guests to see your rental options and prices. From there you can use our filter tool to tailor your search by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday rentals in Pine Top?
Good news! Yes. You can choose from 17 holiday rentals that cater to pets in Pine Top. Lots of our pet-friendly holiday rentals come with an outdoor area for your fur child to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.
Can I rent a house with a pool in Pine Top?
Mark the "pool" box in our filter tool and you'll find five houses with private pools in Pine Top on Vrbo. Ball games, gentle soak or noodle joust? Leisure time is up to you when your holiday property comes with its own swimming pool.
What are popular rental amenities in Pine Top?
When it comes to rental amenities that people prefer in Pine Top, a fireplace, nearby museums and a water view are at the top of the list. With Vrbo holiday rentals, you'll enjoy choices to fit your taste and style, whether you're going on a holiday with your partner, your family or even pets.
Are there large group holiday rentals in Pine Top?
With three holiday rentals that can sleep 10 or more people in Pine Top, you won't have to cross anyone off the invite list. From extended family holidays to events like Christmas and birthday parties, Vrbo will help you find a large group rental to match the occasion.
Are there holiday rentals in Pine Top that welcome kids?
Pine Top has 17 family-friendly holiday homes. And discovering a stay that welcomes kiddos is a cinch with our "Properties good for families" filter. In addition to having the whole place to yourselves, you'll have access to perks and amenities like bunk beds, kitchens and private pools.
What are the top attractions for families in Pine Top?
Keep your kids busy at these leading family-friendly attractions in Pine Top:
  • Deltaville Maritime Museum
  • White Stone Beach
  • Compass Entertainment Complex
Are there one-bedroom holiday rentals in Pine Top?
Pine Top has five one-bedroom rentals on offer. Often situated in well-regarded areas because of their smaller size, a one-bedroom rental is ideal if you're travelling with a friend or your partner. And with plenty of home comforts like kitchens and more privacy than a standard hotel, you'll be able to relax while enjoying this fabulous destination.
Can I find two-bedroom holiday rentals in Pine Top?
Gather your family and experience complete comfort and privacy in one of the five two-bedroom holiday homes Pine Top has to offer.
Are there holiday rentals with WiFi in Pine Top?
Pine Top has nine holiday rentals with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to scrolling social media, these Vrbo homes make it a breeze to get online.
How can I find holiday rentals with air conditioning in Pine Top?
Pine Top has 17 holiday rentals where you can relax in air-conditioned comfort. To locate a property on Vrbo that comes with this perk, enter your dates of travel and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Pine Top?
The minimum required age is typically 16, 18 or 21. It can change from property to property on Vrbo, so look at the rules of your preferred Pine Top holiday home before booking your trip.
How long can I rent a holiday rental in Pine Top for?
The length of time you can rent a holiday rental in Pine Top varies according to the property. Simply enter your chosen travel dates to display a list of options offering extended stays. With loads of amenities like washing machines and kitchens, as well as some offering discounted weekly or monthly prices, you're sure to find the perfect place to call your home away from home in Pine Top.