Photo by Pon Xayavong Photography

Gloucester Point holiday rentals

We found 1,452 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Gloucester Point to find one that's perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, such as air conditioning and a TV. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Gloucester Point

Showing deals for:6 Nov - 13 Nov

Exterior
Property grounds
Sunrise from the porch
Property grounds
Exceptional
(145 reviews)

PRIVATE BEACH on the Chesapeake Bay

Gwynn

8% off
AU$6,134
for 7 nights, 1 home
AU$876 per night
includes taxes & fees
PRIVATE BEACH on the Chesapeake Bay
Room
Exterior
Miscellaneous
Miscellaneous
Exceptional
(121 reviews)

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Gloucester

16% off
AU$1,560
for 7 nights, 1 room
AU$223 per night
includes taxes & fees
Charming Quiet Retreat on North River in Historic Gloucester, Virginia
Interior
Indoor spa tub
Interior
Interior
Very good
(5 reviews)

Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

Hayes

6% off
AU$5,182
for 7 nights, 1 cottage
AU$740 per night
includes taxes & fees
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Plenty of room to play tag, fly a kite or ride a bike!
Plenty of room to spread out to play corn hole with water views everywhere!
No other rental home offers this much riverfront acreage in Mathews!
Waterfront view from the kayak. Wide open space for kids and dogs to play
Exceptional
(200 reviews)

Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!

Bohannon

8% off
AU$4,931
for 7 nights, 1 home
AU$704 per night
includes taxes & fees
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
Private kitchen
Exterior
Living area
Dining
Excellent
(5 reviews)

Poquoson 4 bed, 2 bath! Great Langley Access!

Poquoson

15% off
AU$4,394
for 7 nights, 1 home
AU$628 per night
includes taxes & fees
Poquoson 4 bed, 2 bath! Great Langley Access!
Private kitchen
Property grounds
Beach
Living area
Exceptional
(10 reviews)

Beautiful Gwynn’s Island Waterfront Home

Gwynn

8% off
AU$3,909
for 7 nights, 1 home
AU$558 per night
includes taxes & fees
Beautiful Gwynn’s Island Waterfront Home
Living area
Living area
Exterior
Exterior
Excellent
(25 reviews)

Large 4bed 2.5b home w/ fenced in back yard & deck

Gloucester Point

7% off
AU$3,431
for 7 nights, 1 home
AU$490 per night
includes taxes & fees
Large 4bed 2.5b home w/ fenced in back yard & deck
Fully equipped Kitchen with stainless steel appliances
Beautiful Sunrises await you!
Fire Pit and grill next to small pond near deck
Beautiful, open Dining Room
Exceptional
(65 reviews)

The Harbor House - Waterfront Home with Private Pier & Amazing Views!

Onemo

8% off
AU$3,337
for 7 nights, 1 home
AU$477 per night
includes taxes & fees
The Harbor House - Waterfront Home with Private Pier & Amazing Views!
Dining
Exterior detail
Interior
Exceptional
(50 reviews)

Historic B&B located walking distance to the Williamsburg and The College of W&M

Williamsburg

16% off
AU$13,395
for 7 nights, 1 home
AU$1,914 per night
includes taxes & fees
Historic B&B located walking distance to the Williamsburg and The College of W&M
Enjoy the nature views from the new pier
SHADYHURST, a Victorian Farmhouse built in 1921, restored in 2021.
SHADYHURST - a birds eye view
Another birds eye view - SHADYHURST property includes waterfront (East River)
Exceptional
(46 reviews)

Victorian Farmhouse w/ private waterfront & pier at the mouth of Mobjack Bay

Bohannon

8% off
AU$5,783
for 7 nights, 1 home
AU$826 per night
includes taxes & fees
Victorian Farmhouse w/ private waterfront & pier at the mouth of Mobjack Bay
Kitchen
Kitchen
Kitchen
Kitchen
Exceptional
(97 reviews)

Minutes to Colonial Williamsburg, William & Mary, Busch Gardens, Pet Friendly!

Williamsburg

16% off
AU$3,409
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Minutes to Colonial Williamsburg, William & Mary, Busch Gardens, Pet Friendly!
Living area
Exterior detail
Exterior
Interior
Exceptional
(42 reviews)

Amazing Colonial Home a Heart Beat from Colonial Williamsburg & William & Mary

Williamsburg

12% off
AU$15,176
for 7 nights, 1 home
AU$2,168 per night
includes taxes & fees
Amazing Colonial Home a Heart Beat from Colonial Williamsburg & William & Mary
Exterior
Exterior
Outdoor dining
Property grounds
Excellent
(5 reviews)

4 Bedroom Lockoff Suite at Williamsburg Governors Green!!

Williamsburg

8% off
AU$12,502
for 7 nights, 1 apartment
AU$1,786 per night
includes taxes & fees
4 Bedroom Lockoff Suite at Williamsburg Governors Green!!
Comfy leather chairs, one swivel to view golf course and one with ottoman
Premiere River Golf Course View
Comfortable Sleep Sofa
Living area
Exceptional
(78 reviews)

Stunning 1 Bedroom condo on River Golf Course Ninth Hole.

Williamsburg

7% off
AU$2,457
for 7 nights, 1 apartment
AU$351 per night
includes taxes & fees
Stunning 1 Bedroom condo on River Golf Course Ninth Hole.
Interior
Exterior detail
Exterior
Dining
Exceptional
(35 reviews)

History Filled Bed & Breakfast in Downtown Williamsburg

Williamsburg

12% off
AU$15,607
for 7 nights, 1 room
AU$2,230 per night
includes taxes & fees
History Filled Bed & Breakfast in Downtown Williamsburg
Beach
Beach
Welcome to your very own private beach vacation.
Exterior detail
Exceptional
(42 reviews)

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

Gwynn

8% off
AU$3,226
for 7 nights, 1 home
AU$461 per night
includes taxes & fees
Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!
Room
Exterior
Property grounds
Room
Exceptional
(55 reviews)

Family friendly home near Colonial Williamsburg and Busch Gardens

Williamsburg

8% off
AU$3,576
for 7 nights, 1 home
AU$511 per night
includes taxes & fees
Family friendly home near Colonial Williamsburg and Busch Gardens
Dining
Property grounds
Interior
Living area
Exceptional
(19 reviews)

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

Gwynn

8% off
AU$4,818
for 7 nights, 1 home
AU$688 per night
includes taxes & fees
Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home
Living area
Living area
Large and spacious living room suite with plenty of seating.
Enjoy dining at the Marina bar and grill
Exceptional
(31 reviews)

Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!

Williamsburg

7% off
AU$2,943
for 7 nights, 1 apartment
AU$420 per night
includes taxes & fees
Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!
Private kitchen
Exterior
Living area
Outdoor dining
Exceptional
(31 reviews)

3 bedroom in Williamsburg - Next to Busch Gardens!

Williamsburg

9% off
AU$4,166
for 7 nights, 1 home
AU$595 per night
includes taxes & fees
3 bedroom in Williamsburg - Next to Busch Gardens!
Private kitchen
Terrace/patio
Property grounds
Golf
Wonderful
(17 reviews)

Lovely condo with water & golf course view

Williamsburg

8% off
AU$2,272
for 7 nights, 1 apartment
AU$325 per night
includes taxes & fees
Lovely condo with water & golf course view
Private kitchen
Property grounds
Living area
Room
Exceptional
(48 reviews)

Kingsmill Luxury - Sleeps 6 - Virginia's only AAA Four Diamond Condo Golf Resort

Williamsburg

11% off
AU$4,502
for 7 nights, 1 apartment
AU$643 per night
includes taxes & fees
Kingsmill Luxury - Sleeps 6 - Virginia's only AAA Four Diamond Condo Golf Resort
Hand-held showerhead
Property grounds
Bathroom
Hand-held showerhead
Exceptional
(5 reviews)

Blanchard Farm Camper Stay

Diggs

8% off
AU$1,783
for 7 nights, 1 home
AU$255 per night
includes taxes & fees
Blanchard Farm Camper Stay
  • 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

The friendly city of Gloucester Point awaits you

Learn about the unique charm of Gloucester Point with a stay in a holiday home rental. This welcoming city has many special qualities. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Gloucester Point

Are you hoping to discover attractions to see while you're in the area? Venture out of your holiday home and check out everything that makes Gloucester Point a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Busch Gardens Williamsburg (8.2 mi / 13.2 km)
  • Water Country USA (7.5 mi / 12.1 km)
  • Kingsmill Plantation Golf Course (9.5 mi / 15.4 km)
  • Golden Horseshoe Golf Club (11.2 mi / 18 km)
  • Williamsburg Winery (12.3 mi / 19.8 km)
  • Ford's Colony at Williamsburg (15.8 mi / 25.5 km)

Exploring the natural landscape of Gloucester Point

Whether you're an active traveller or just want to spend some time taking in the scenery, Gloucester Point is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Yorktown Beach (1.3 mi / 2 km)
  • Newport News Park (6.7 mi / 10.9 km)
  • Fossil Beach (15.8 mi / 25.4 km)
  • Jamestown Beach (16.2 mi / 26.1 km)
  • Huntington Beach (16.7 mi / 26.8 km)
  • Chesapeake Bay (28.4 mi / 45.6 km)

How to get to and around Gloucester Point

Fly into Newport News, VA (PHF-Newport News - Williamsburg Intl.), the closest airport, located 8.4 mi (13.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Norfolk, VA (ORF-Norfolk Intl.), which is 29.3 mi (47.2 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Gloucester Point?
Based on our data, cottages are considered the most popular type of holiday home in Gloucester Point. But as you'd expect, everyone's idea of an awesome stay can differ. Stayz has holiday homes in a variety of shapes and sizes, and we'll help you locate your ideal fit.
How much does it cost to rent a holiday home in Gloucester Point?
The average price for a holiday home in Gloucester Point can vary depending on factors including property type, season and length of stay. Whether you're thinking about a sprawling villa with room to move around or a quaint cabin just for the two of you, just enter your travel dates to view stays with unbeatable value.
How much does it cost to rent a beach house in Gloucester Point?
Prices for beach houses in Gloucester Point can differ depending on the type and size of the property and when you're travelling. Simply enter your dates of travel into Stayz and the number of guests to view your home options and prices. From there you can use the filters to narrow your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Gloucester Point?
With three properties that host four-legged guests, your happy hound can join in the fun on your Gloucester Point holiday. Use the filter tool to browse our pet-friendly holiday homes and find the pawfect pad on Stayz.
What are popular home amenities in Gloucester Point?
When it comes to home amenities that guests search for in Gloucester Point, a nearby waterfront, a water view and nearby museums rank highest. With Stayz holiday homes, you'll discover options to suit your taste and style, whether you're going on a holiday with friends, family or even pets.
Are there holiday homes in Gloucester Point that welcome kids?
Bring the whole family together for fun-filled adventures in Gloucester Point at one of our three family-friendly holiday properties. A lot of these stays provide conveniences that are perfect for getaways with the little ones, such as laundries, bunk beds and swimming pools. Just click on the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Gloucester Point?
If you've got the little ones in tow, be sure to include these family-friendly attractions in Gloucester Point on your list of things to do:
  • Middle Peninsula State Park
  • Rosewell Ruins
Are there holiday homes with WiFi in Gloucester Point?
Pick from two holiday homes with WiFi in Gloucester Point. If you want to disconnect from daily life while on holiday, but still want to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Gloucester Point?
Gloucester Point has three holiday homes where you can wind down in air-conditioned comfort. To find a stay on Stayz offering this amenity, 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 home in Gloucester Point?
The minimum age requirements can vary across properties on Stayz, so double-check the rules of the holiday home in Gloucester Point you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Gloucester Point for?
It really depends on the Gloucester Point property. To see all available options offering extended stays, simply enter your dates and number of guests into the Stayz search page. Enjoy having the entire property to yourself, along with amenities such as a fully-equipped kitchen and outdoor spaces where your little ones can play. Be on the lookout for long-term stays that offer weekly or monthly discounts.