Gloucester holiday rentals

We found 472 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:18 Dec - 25 Dec

Beach
Property grounds
Exterior
Property grounds
Exceptional
(150 reviews)

PRIVATE BEACH on the Chesapeake Bay

Gwynn

8% off
AU$6,085
for 7 nights, 1 home
AU$869 per night
includes taxes & fees
PRIVATE BEACH on the Chesapeake Bay
Exterior
Property grounds
Room
Living area
Exceptional
(124 reviews)

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Gloucester

16% off
AU$1,547
for 7 nights, 1 room
AU$221 per night
includes taxes & fees
Charming Quiet Retreat on North River in Historic Gloucester, Virginia
Exterior
Property grounds
Interior
Property grounds
Very good
(5 reviews)

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

Hayes

6% off
AU$5,040
for 7 nights, 1 cottage
AU$720 per night
includes taxes & fees
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Marina
Outdoor dining
Living area
Marina
Exceptional
(76 reviews)

Enjoy family fun and Sunsets at Piankatank Point.

Saluda

8% off
AU$3,843
for 7 nights, 1 home
AU$549 per night
includes taxes & fees
Enjoy family fun and Sunsets at Piankatank Point.
Spacious back porch/utility room
Plenty of room to play tag, fly a kite or ride a bike!
The parking area has all the space you need. And it's safe and secure!
Completely remodeled kitchen. Double ovens and 5-burner cooktop
Exceptional
(203 reviews)

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

Bohannon

8% off
AU$5,214
for 7 nights, 1 home
AU$745 per night
includes taxes & fees
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
Property grounds
Waterfront home with amazing views!
Fully equipped Kitchen with stainless steel appliances
Dining Room table comfortably seats 10
Exceptional
(69 reviews)

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

Onemo

8% off
AU$3,310
for 7 nights, 1 home
AU$473 per night
includes taxes & fees
The Harbor House - Waterfront Home with Private Pier & Amazing Views!
Interior
Exterior detail
Interior
Property grounds
Exceptional
(47 reviews)

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

Gwynn

8% off
AU$3,200
for 7 nights, 1 home
AU$457 per night
includes taxes & fees
Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!
Dining
Private kitchen
Living area
Interior
Exceptional
(33 reviews)

3 bedroom in Williamsburg - Next to Busch Gardens!

Williamsburg

9% off
AU$4,093
for 7 nights, 1 home
AU$585 per night
includes taxes & fees
3 bedroom in Williamsburg - Next to Busch Gardens!
Dining
Interior
Interior
Living area
Exceptional
(21 reviews)

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

Gwynn

8% off
AU$4,779
for 7 nights, 1 home
AU$683 per night
includes taxes & fees
Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home

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    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)
  • Bounce House (13.2 mi / 21.3 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)
  • Urbanna Historic District (15.9 mi / 25.6 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 rental?
When considering the best area to stay in Gloucester, Virginia for a holiday rental, the historic village is an excellent choice. This charming neighbourhood is known for its quaint atmosphere and picturesque surroundings. Visitors can explore the nearby Gloucester Point Beach Park, which offers lovely views of the Chesapeake Bay and is superb for a relaxing day outdoors. Additionally, the area is home to the impressive Historic Courthouse, where you can appreciate local architecture and learn about the region's rich history.Another appealing option is the outskirts of Gloucester, where you can find properties located near nature. This area provides access to a variety of outdoor activities, including hiking and kayaking, particularly around the beautiful Mathews County and the surrounding waterways. Here, you can truly immerse yourself in the natural beauty of Virginia while enjoying a peaceful retreat.Overall, Gloucester boasts a variety of properties, from quaint cottages to larger family homes, suiting different preferences and group sizes.
Where are the best areas for renting a beach house in Gloucester?
For renting a beach house in Gloucester, Virginia, consider the picturesque waterfront areas along the Chesapeake Bay. The vicinity near Ware Neck offers a tranquil setting with access to sandy beaches and stunning views of the bay. Many holiday rentals in this area come equipped with amenities like private docks, outdoor seating areas, and fully stocked kitchens, ideal for families or groups looking to enjoy a seaside getaway.Additionally, the area around Gloucester Point is another excellent choice, featuring properties that provide easy access to the beach and local marinas. Rentals here often include features such as screened porches, fire pits for evening gatherings, and spacious living areas to accommodate larger groups. The nearby York River also offers opportunities for fishing and boating, making it a fantastic choice for water enthusiasts.For those interested in exploring local attractions, Gloucester has a rich historical background, with nearby points of interest including the Colonial Court House and various parks offering hiking trails. Rentals in this charming region often blend comfort with convenience, providing close proximity to both the beach and cultural sites.
What is the most popular type of holiday rental accomodation in Gloucester?
In Gloucester, holiday houses are the most popular type of holiday rental, with around 60 available throughout the area. These properties typically provide spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also feature outdoor spaces such as gardens or patios, superb for enjoying the pleasant Virginia climate. Additionally, there are about 44 charming cottages that offer a cozy atmosphere and often include amenities like fireplaces and rustic decor, enhancing the tranquil experience of the surrounding countryside. For those seeking a different stay, approximately 12 apartments are available, mainly located near local attractions and waterfront areas, providing convenience and comfort. Gloucester also has several campsites and condos for those looking for alternative accommodations.
Are there any family house rentals in Gloucester?
In Gloucester, Virginia, there are numerous family-friendly holiday rentals available, with around 23 properties to choose from. This charming area offers a variety of homes that cater to families, featuring spacious living areas that allow for relaxation and socialising. Many of these accommodations come equipped with full kitchens, making it convenient for guests to prepare meals together after a day of exploring.Visitors can find amenities such as outdoor spaces, ideal for children to play, and some properties may even include features like game rooms or access to nearby parks. The historic charm of Gloucester, combined with its proximity to the scenic York River, provides plenty of opportunities for outdoor activities such as fishing, boating, and hiking.
Can I rent a holiday home with a pool or hot tub in Gloucester?
In Gloucester, Virginia, there are several holiday homes available for rent that feature pools and hot tubs. This charming town offers a picturesque setting along the York River, great for those looking to relax in a tranquil environment. Many properties come with amenities such as private swimming pools, outdoor hot tubs, and spacious patios or decks for enjoying the scenic views.Travellers can also expect fully equipped kitchens, allowing for convenient self-catering during their stay. Some rentals may include additional features like barbecue facilities and ample outdoor space, making them ideal for families or groups seeking a comfortable getaway.
Are there pet-friendly house rentals in Gloucester?
In Gloucester, Virginia, there are several pet-friendly house rentals available, with a total of 13 options to choose from. Many of these holiday homes are situated near scenic waterfront areas, providing lovely views and easy access to the surrounding natural beauty. Travellers can expect amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, which are superb for families or groups travelling with pets.The area also offers nearby parks and natural attractions where pets are welcome, allowing for enjoyable outdoor experiences. In particular, the charming local parks provide walking trails and picnic areas, making it easy for pet owners to enjoy time outdoors with their furry companions.
Are there any remote work holiday rentals in Gloucester?
In Gloucester, Virginia, there are plenty of remote work holiday rentals available, with around 120 options to choose from. This charming town offers a peaceful atmosphere, ideal for those working remotely while enjoying a scenic environment. Many properties come equipped with essential amenities such as complimentary Wi-Fi, spacious work areas, and comfortable living spaces, ensuring that you can maintain productivity during your stay.The area boasts a mix of waterfront homes and cosy cottages, often featuring outdoor patios or decks where you can unwind after a day of work. Gloucester is also close to various points of interest, including the picturesque York River and local parks, providing opportunities for relaxation and recreation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Gloucester?
In Gloucester, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals and enjoy home-cooked comfort. Many properties feature outdoor decks or patios, providing a nice space to relax and take in the natural surroundings. Additionally, rentals often come equipped with modern conveniences such as blenders and coffee or tea makers, ensuring that guests can start their day with a fresh brew. Onsite parking is typically available, making it convenient for visitors with vehicles.
When is the best time to visit Gloucester for a holiday rental?
The best time to visit Gloucester for a holiday rental is during the peak season from June to August. This vibrant period attracts families and outdoor enthusiasts looking to enjoy the warm summer weather and a variety of activities. With temperatures typically ranging from the mid-20s to low 30s Celsius, it's great for leisurely days spent at the beach, exploring local parks, or engaging in water sports on the beautiful Chesapeake Bay.July stands out as the most popular month, bustling with visitors eager to experience Gloucester's charm. The lively option is enhanced by various local events and festivals, providing ample opportunities for socialising and enjoying the community spirit.If you're seeking a more budget-friendly option, consider visiting in December. While this is part of the low season, it offers a unique opportunity to explore Gloucester's historical sites without the usual crowds. The festive decorations and seasonal events create a warm, welcoming environment, making it a lovely time for a quieter getaway.Ultimately, the best time to visit Gloucester will depend on your preferences—whether you want the energetic buzz of summer activities or the peaceful charm of winter explorations.
What are the top attractions in Gloucester?
In Gloucester, Virginia, visitors can enjoy a variety of attractions that showcase the area's natural beauty and rich history. The historic Gloucester Court House area features charming shops, local eateries, and the Gloucester Museum of History, where guests can learn about the region's past. For those interested in outdoor activities, the nearby Ware River offers opportunities for kayaking and fishing, with beautiful waterfront views.Additionally, the surrounding countryside is home to scenic parks, such as the Beaverdam Park, which boasts walking trails and picnic areas, making it ideal for family outings and nature walks.
Are all fees included in the Gloucester 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 Gloucester holiday homes with parking?
Stayz offers a wide selection of holiday homes in Gloucester 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 Gloucester holiday homes?
You can find great discounts on holiday homes in Gloucester 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 Gloucester holiday home booking on Stayz?
To find Gloucester 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 Gloucester?
A long-stay holiday home in Gloucester 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 Gloucester holiday home?
Book your Gloucester 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 Gloucester?
Prices for holiday homes in Gloucester 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 Gloucester 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.

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