Gloucester holiday homes

We found 493 holiday rentals — enter your dates for availability
Select from 18 homes, 14 cottages and other holiday rentals in Gloucester to find one that's perfect for your trip. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as parking and a TV. You're 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 – Gloucester

Showing deals for:13 Nov - 20 Nov

Beach
Property grounds
Property grounds
Dining
Exceptional
(145 reviews)

PRIVATE BEACH on the Chesapeake Bay

Gwynn

8% off
NZ$7,456
for 7 nights, 1 home
NZ$1,065 per night
includes taxes & fees
PRIVATE BEACH on the Chesapeake Bay
Long pier with a pergola - great for watching sunsets/sunrises and for fishing!
Large deck overlooking the Bay
Aerial view of the property
Living area
Exceptional
(20 reviews)

Spectacular waterfront property with breathtaking views of the Chesapeake Bay!

Deltaville

8% off
NZ$8,236
for 7 nights, 1 home
NZ$1,177 per night
includes taxes & fees
Spectacular waterfront property with breathtaking views of the Chesapeake Bay!
Exterior
Property grounds
Property grounds
Interior
Very good
(5 reviews)

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

Hayes

6% off
NZ$6,192
for 7 nights, 1 cottage
NZ$885 per night
includes taxes & fees
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Living area
Property grounds
Room
Exterior
Exceptional
(121 reviews)

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Gloucester

16% off
NZ$1,867
for 7 nights, 1 room
NZ$267 per night
includes taxes & fees
Charming Quiet Retreat on North River in Historic Gloucester, Virginia
The floating dock makes it easy for swimmers to get in and our of the water.
Enjoy the nature views from the new pier
SHADYHURST - a birds eye view
A favorite spot to enjoy a good read and coffee.
Exceptional
(46 reviews)

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

Bohannon

8% off
NZ$6,994
for 7 nights, 1 home
NZ$999 per night
includes taxes & fees
Victorian Farmhouse w/ private waterfront & pier at the mouth of Mobjack Bay
Fully equipped Kitchen with stainless steel appliances
Waterfront home with amazing views!
The pampas grass makes you feel like you are sitting at the ocean
Dining Room table comfortably seats 10
Exceptional
(66 reviews)

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

Onemo

8% off
NZ$3,993
for 7 nights, 1 home
NZ$570 per night
includes taxes & fees
The Harbor House - Waterfront Home with Private Pier & Amazing Views!
Interior
Living area
Living area
Room
Excellent
(25 reviews)

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

Gloucester Point

7% off
NZ$3,697
for 7 nights, 1 home
NZ$528 per night
includes taxes & fees
Large 4bed 2.5b home w/ fenced in back yard & deck
Completely remodeled kitchen. Double ovens and 5-burner cooktop
Plenty of room to play tag, fly a kite or ride a bike!
Spacious back porch/utility room
The parking area has all the space you need. And it's safe and secure!
Exceptional
(200 reviews)

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

Bohannon

8% off
NZ$6,251
for 7 nights, 1 home
NZ$893 per night
includes taxes & fees
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
Property grounds
Exterior detail
Interior
Interior
Exceptional
(44 reviews)

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

Gwynn

8% off
NZ$3,940
for 7 nights, 1 home
NZ$563 per night
includes taxes & fees
Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!
Interior
Interior
Dining
Interior
Exceptional
(19 reviews)

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

Gwynn

8% off
NZ$5,885
for 7 nights, 1 home
NZ$841 per night
includes taxes & fees
Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home
Back deck overlooking the York River
The Island Cottage
Fall morning looking out over the river
Built in bookcases with games and DVDs.
Exceptional
(381 reviews)

Cottage on a Private Island in the York River

Hayes

7% off
NZ$2,695
for 7 nights, 1 cottage
NZ$385 per night
includes taxes & fees
Cottage on a Private Island in the York River
Dining
Room
Interior
Property grounds
Exceptional
(102 reviews)

Minutes from Busch Gardens-Water Country-Colonial Williamsburg-William&Mary

Williamsburg

12% off
NZ$2,047
for 7 nights, 1 home
NZ$292 per night
includes taxes & fees
Minutes from Busch Gardens-Water Country-Colonial Williamsburg-William&Mary
Outdoor dining
Private kitchen
Living area
Dining
Exceptional
(31 reviews)

3 bedroom in Williamsburg - Next to Busch Gardens!

Williamsburg

9% off
NZ$5,011
for 7 nights, 1 home
NZ$716 per night
includes taxes & fees
3 bedroom in Williamsburg - Next to Busch Gardens!

  • 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

Why people love visiting historical Gloucester

Take a holiday to Gloucester and enjoy the area's festivals, history and art galleries. This city is well-known for its camping and wildlife. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Gloucester

Are you looking for top things to see and do during your stay? Venture out of your holiday home and check out everything that makes Gloucester a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Busch Gardens Williamsburg (13.8 mi / 22.2 km)
  • Water Country USA (11.8 mi / 19.1 km)
  • Kiskiack Golf Club (12.6 mi / 20.3 km)
  • Golden Horseshoe Golf Club (13.7 mi / 22 km)
  • Colonial Heritage Golf Club (13.9 mi / 22.4 km)
  • Kingsmill Plantation Golf Course (14.9 mi / 23.9 km)

Exploring the natural features in Gloucester

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Gloucester is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Fossil Beach (9.8 mi / 15.8 km)
  • Cuba Island (11.7 mi / 18.8 km)
  • Yorktown Beach (12 mi / 19.2 km)
  • Bethel Beach Natural Area Preserve (15 mi / 24.2 km)
  • Williamsburg Botanical Garden (16.2 mi / 26.1 km)
  • Newport News Park (17.6 mi / 28.4 km)

Travelling to and around Gloucester

Fly into Newport News, VA (PHF-Newport News - Williamsburg Intl.), the closest airport, located 19.3 mi (31.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Norfolk, VA (ORF-Norfolk Intl.), which is 39.5 mi (63.5 km) away.

Frequently asked questions

What is the best area to stay in Gloucester when booking a holiday home?
If you're organising a Gloucester trip, Schley is one of the most desirable places to stay. Whether you go for a condo, cottage or another property type, you'll always have the whole place to yourself.
What is the most popular type of holiday home accommodation in Gloucester?
The most popular types of holiday homes in Gloucester are farmhouses. Want something different? Bookabach has numerous options to match our guests' needs, so you'll see properties in loads of shapes and sizes. The perfect home away from home is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Gloucester?
A number of things affect how much you'll pay for a holiday home in Gloucester, like the time of year, length of stay and property type. However, all Bookabach homes have something in common — unbeatable value. Just add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Gloucester?
The average price for a holiday home by the beach in Gloucester will depend on when you'll be there and the size and style of property you're searching for. You can easily and quickly find prices on Bookabach by entering your preferred travel dates. Then use our handy filter tool to pick the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday homes in Gloucester?
Pack a squeezy toy and a bone for your pooch because Gloucester has eight stays that open their doors to pets. Let your four-legged buddy join in with the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates then check the "Pets allowed" filter box.
What are popular home amenities in Gloucester?
A nearby river, a nearby waterfront and a garden top the list of most popular home amenities in Gloucester. Whether you're heading away alone, with your better half or a bunch of friends, Bookabach will help you find a holiday home that matches your tastes with all the options you need.
Are there large group holiday homes in Gloucester?
Gloucester has two holiday homes that can host 10 or more guests. These properties come with plenty of space to enjoy good times with your nearest and dearest.
Are there holiday homes in Gloucester that welcome kids?
Bring the entire family together for a memorable adventure in Gloucester at one of our eight family-friendly properties. A lot of these stays come with amenities that are perfect for trips with children, such as kitchens, living rooms and patios. Just click on the "Properties good for families" filter and pick your favourite.
What are the top attractions for families in Gloucester?
There are plenty of amazing things to do and see with the family in Gloucester, including:
  • Gloucester Museum of History
  • Middle Peninsula State Park
  • Rosewell Ruins
Can I find two-bedroom holiday homes in Gloucester?
Gather your besties and experience complete comfort and privacy in one of the three two-bedroom holiday properties Gloucester has to offer.
Are there holiday homes with WiFi in Gloucester?
Whether you'd like to keep up with the headlines, write a few emails or surf social media, there are two holiday homes with WiFi in Gloucester. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Gloucester?
Select your dates and then make use of our filters to search for holiday homes with air conditioning in Gloucester on Bookabach. With eight air-conditioned properties to choose from here, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday home in Gloucester?
The minimum required age is generally 16, 18 or 21. It can vary from property to property on Bookabach, so check the rules of your preferred Gloucester holiday home before booking.
How long can I rent a holiday home in Gloucester for?
It really depends on the Gloucester property. To look at a list of options offering extended stays, simply type your travel dates and number of people into the Bookabach search page. You can look forward to having the entire place to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and a yard to play in. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.