Photo by Kacy Kish

Pine Top holiday rentals

We found 239 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:22 Jan - 29 Jan

Marina
Outdoor dining
Private kitchen
Marina
Exceptional
(76 reviews)

Enjoy family fun and Sunsets at Piankatank Point.

Saluda

7% off
S$3,611
for 7 nights, 1 home
S$516 per night
includes taxes & fees
Enjoy family fun and Sunsets at Piankatank Point.
Fire pit
Living area
Upstairs porch with queen bed (no private entrance,)
Interior
Exceptional
(148 reviews)

Gorgeous Waterfront Estate--Private Pool, Pier, Tennis Court, Firepit

Foster

8% off
S$5,586
for 7 nights, 1 home
S$798 per night
includes taxes & fees
Gorgeous Waterfront Estate--Private Pool, Pier, Tennis Court, Firepit
Dining
Property grounds
Exterior
Beach
Exceptional
(150 reviews)

PRIVATE BEACH on the Chesapeake Bay

Gwynn

8% off
S$5,768
for 7 nights, 1 home
S$824 per night
includes taxes & fees
PRIVATE BEACH on the Chesapeake Bay
Property grounds
Bahamas? in White Stone
Large open concept - perfect for entertaining!
Interior
Excellent
(20 reviews)

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

White Stone

10% off
S$5,031
for 7 nights, 1 home
S$719 per night
includes taxes & fees
BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock
Interior
Exterior
Private kitchen
The Rosé Retreat is ready for your next getaway!
Exceptional
(26 reviews)

The Rosé Retreat: Pool-Screened Porch-RELAX

Irvington

8% off
S$3,140
for 7 nights, 1 home
S$449 per night
includes taxes & fees
The Rosé Retreat: Pool-Screened Porch-RELAX
Private kitchen
Interior
Interior
Interior
Exceptional
(12 reviews)

Beautiful Gwynn’s Island Waterfront Home

Gwynn

8% off
S$3,580
for 7 nights, 1 home
S$511 per night
includes taxes & fees
Beautiful Gwynn’s Island Waterfront Home
Start slow with your favorite morning coffee before heading out to the dock, kayaks, or nearby oyster trail.
Rainy days call for getting the kids out of the house and staying active. Compass Entertainment has both indoor and outdoor games including batting cages, putt-putt golf, a movie theatre, and on site restaurant and bar.
An open gathering space makes it easy to reconnect after a day on the water, with the outside dining area just outside the door.
Original hardwood floors and a decorative fireplace give this spacious room timeless farmhouse character.
Exceptional
(26 reviews)

Waterfront Getaway: Hot Tub, Dock & Kayaks

White Stone

7% off
S$4,810
for 7 nights, 1 home
S$687 per night
includes taxes & fees
Waterfront Getaway: Hot Tub, Dock & Kayaks
Terrace/patio
Living area
Dining
Living area
Exceptional
(7 reviews)

Heron's Landing at Sunset Cove - Pet Friendly!

Weems

8% off
S$2,170
for 7 nights, 1 home
S$310 per night
includes taxes & fees
Heron's Landing at Sunset Cove - Pet Friendly!
Living area
Property grounds
Room
Exterior
Exceptional
(125 reviews)

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Gloucester

15% off
S$1,459
for 7 nights, 1 room
S$208 per night
includes taxes & fees
Charming Quiet Retreat on North River in Historic Gloucester, Virginia
Interior
Interior
Property grounds
Living area
Exceptional
(31 reviews)

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

White Stone

8% off
S$2,110
for 7 nights, 1 cottage
S$301 per night
includes taxes & fees
Charming Spacious Cottage, private, water views, close to amenities
Interior
Exterior detail
Interior
Property grounds
Exceptional
(47 reviews)

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

Gwynn

8% off
S$3,005
for 7 nights, 1 home
S$429 per night
includes taxes & fees
Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!
Living area
Interior
Interior
Interior
Exceptional
(21 reviews)

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

Gwynn

8% off
S$4,493
for 7 nights, 1 home
S$642 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$1,939
for 7 nights, 1 home
S$277 per night
includes taxes & fees
1891 Coastal Charmer: fully renovated farmhouse
Private kitchen
Property grounds
Miscellaneous
Room
Exceptional
(5 reviews)

Charming studio in lovely Topping with AC, WiFi that has stunning water views!

Topping

12% off
S$1,744
for 7 nights, 1 apartment
S$249 per night
includes taxes & fees
Charming studio in lovely Topping with AC, WiFi that has stunning water views!
Outdoor dining
Exterior
Interior
Marina
Exceptional
(47 reviews)

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

Weems

8% off
S$2,159
for 7 nights, 1 home
S$308 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)
  • Piankatank River Golf Club (3.8 mi / 6 km)
  • Compass Entertainment Complex (9.1 mi / 14.6 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)
  • Chesapeake Bay (17.1 mi / 27.5 km)
  • Fossil Beach (19 mi / 30.5 km)
  • Thousand Trails Beach Park (6.1 mi / 9.8 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.