Gloucester vacation rentals

We found 494 vacation rentals — enter your dates for availability

Select from 16 homes, 13 cottages, and other vacation rentals in Gloucester to find one that's perfect for your trip. Vacation rentals provide the amenities you need and want for your stay with friends, family, or just your pet, like air conditioning and cable TV. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Gloucester

Showing deals for:Aug 7 - Aug 14

Image gallery for Waterfront with Private Pier and Tranquil Water views!

Private dock and boathouse
10 out of 10, Exceptional, (108 reviews)
Exceptional
(108 reviews)

Waterfront with Private Pier and Tranquil Water views!

Gloucester

9% off
Price is $248
$1,737 for 7 nights
All fees included
Waterfront with Private Pier and Tranquil Water views!

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Find out more about Gloucester

Why visit Gloucester

  • Outdoor Adventures: Gloucester offers stunning scenery, perfect for outdoor enthusiasts and families, with beautiful islands and national parks to explore.
  • Historical Significance: Visit the Gloucester Courthouse for a touch of local history and charm.
  • Charming Downtown: Experience the blend of rustic charm and historical significance in the quaint downtown area.
  • Beach Getaway: Enjoy nearby beaches that provide a perfect setting for relaxation and fun.
  • Welcoming Atmosphere: Friendly locals and a warm community spirit ensure a memorable experience for all visitors.

Popular types of accommodation in Gloucester

Planning your getaway to Gloucester? Explore a variety of popular vacation rentals, including private homes, condos, and cozy cottages. Whether you're seeking affordable options or unique Airbnb stays, Gloucester has something for everyone. Enjoy essential amenities and the charm of Gloucester Courthouse, Virginia, ensuring your stay is comfortable and memorable. Discover the perfect home base for your adventures in this beautiful area.

  • Houses: The top choice for visitors in Gloucester, these homes provide a spacious and comfortable setting for families, groups, or couples looking for a home-away-from-home experience.
  • Condos: A popular option for those seeking modern amenities and convenient locations, condos offer a blend of comfort and community.
  • Cottages: Charming and cozy, cottages in Gloucester offer a quaint retreat that embodies the local character and charm.
  • Cabins: Ideal for nature lovers, cabins provide a rustic getaway surrounded by beautiful landscapes.
  • Apartments: A practical choice for solo travelers or couples, apartments offer convenience and a home-like feel in the heart of Gloucester.**

Top attractions in Gloucester

Gloucester, Virginia, is perfect for outdoor and family vacations, offering stunning scenery and various attractions. Visitors can explore beautiful islands, beaches, and national parks that cater to outdoor enthusiasts and families alike. A notable point of interest is the Gloucester Courthouse, which adds a touch of history to your trip. Discover the charm of Gloucester as you enjoy its diverse recreational opportunities and picturesque landscapes.

  • Rosewell Ruins: Explore the haunting beauty of the Rosewell Ruins, remnants of an 18th-century plantation. The site offers a glimpse into the area's cultural history, surrounded by picturesque landscapes that evoke a sense of nostalgia.
  • Middle Peninsula State Park: Experience adventure and stunning scenery at Middle Peninsula State Park. This national park features trails, waterways, and picnic areas, perfect for outdoor enthusiasts seeking a day of hiking, fishing, or kayaking.
  • Gloucester Museum of History: Dive into the rich heritage of the region at the Gloucester Museum of History. With engaging exhibits, the museum showcases local artifacts and stories, offering a deeper understanding of Gloucester's cultural roots.

Things to do recommended for couples

Gloucester, Virginia, offers couples a charming getaway. Explore the scenic trails of Beaverdam Park, enjoy a sunset cruise on the York River, or have a romantic dinner at a riverside restaurant. Don't miss the local wineries for a delightful wine tasting experience together.

Things to do recommended for families

In Gloucester, families can explore the enchanting woods of Beaverdam Park, enjoy a fun day at the historic Gloucester Point Beach, or visit the interactive exhibits at the Virginia Institute of Marine Science. Each experience offers a unique way to connect with nature and learn together.

Things to do recommended for groups

Groups visiting Gloucester can enjoy a guided tour of historic sites like the Gloucester Museum, take a scenic boat ride on the York River, and indulge in local seafood at charming waterfront restaurants, perfect for a memorable experience together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Gloucester

When you're planning a trip, whether with a group, family, pets, or for an extended stay, be sure to prioritize your filters appropriately. Here are some helpful booking tips for Vrbo.

  • Traveling to Gloucester with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Gloucester with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Gloucester: For many families, a vacation isn't truly enjoyable without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Gloucester: If you're searching for vacation rentals that offer great deals for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Gloucester

Gloucester, Virginia, offers a delightful blend of outdoor adventures and family-friendly activities. Explore the charming downtown area, where rustic charm meets historical significance. Enjoy a beach getaway nearby, or venture into Gloucester County to immerse yourself in scenic landscapes. The welcoming atmosphere and friendly locals make every moment special, ensuring a memorable experience for visitors of all ages.

  • North: North is a charming city located 6 miles from Gloucester, offering visitors a delightful outdoor experience along its picturesque beaches and scenic bay. Travelers flock to North for its beautiful boardwalks and the fun-filled amusement park, making it an ideal destination for families and adventure seekers. With access to stunning lakes and coastal views, North is perfect for those looking to enjoy water activities, picnicking, or simply unwinding in nature. The serene environment and vibrant local atmosphere make it a must-visit spot for anyone seeking a refreshing getaway.
  • Ware Neck: Nestled within Gloucester, Ware Neck is a quaint village that exudes a romantic and entertaining ambiance. Ideal for couples and families alike, it features a delightful boardwalk and an arcade adventure zone that promises fun for all ages. The nearby nature reserve invites visitors to explore lush landscapes while the local archaeology and anthropology museum offers a glimpse into the area's rich history. Ware Neck's blend of outdoor activities and cultural attractions makes it an enchanting place to spend a day or two, perfect for creating cherished memories.
  • Zanoni: Zanoni is a picturesque village within the Gloucester area, known for its family-friendly atmosphere and outdoor adventures. Visitors can enjoy various activities, including a lively boardwalk and an amusement park, ensuring a fun-filled experience for children and adults alike. The proximity to beautiful beaches and serene lakes allows for relaxing days by the water, making it an ideal spot for family gatherings and picnics. With its charming environment and abundance of recreational opportunities, Zanoni invites you to create lasting memories in this delightful setting.

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as this can lead to significant price differences. Moreover, extending your stay can often result in even better savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, refine your travel arrangements, or manage your existing bookings. Your saved or reserved properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting historic Gloucester

Take a vacation 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 vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Gloucester

Are you hoping to discover top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Gloucester a one-of-a-kind vacation spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Busch Gardens Williamsburg (13.8 mi / 22.2 km)
  • Water Country USA (11.8 mi / 19.1 km)
  • Golden Horseshoe Golf Club (13.7 mi / 22 km)
  • Kingsmill Plantation Golf Course (14.9 mi / 23.9 km)
  • Ford's Colony at Williamsburg (15.3 mi / 24.6 km)
  • Williamsburg Winery (16.2 mi / 26 km)

Exploring the natural features in Gloucester

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Gloucester is a great place to get outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Fossil Beach (9.8 mi / 15.8 km)
  • Cuba Island (11.7 mi / 18.8 km)
  • Yorktown Beach (12 mi / 19.2 km)
  • Quarterpath Park (13.2 mi / 21.3 km)
  • Williamsburg Botanical Garden (16.2 mi / 26.1 km)
  • White Stone Beach (16.8 mi / 27 km)

Traveling to and around Gloucester

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

Frequently asked questions

What is the best area to stay in Gloucester, Virginia, United States of America when booking a vacation rental?
When considering a vacation rental in Gloucester, Virginia, the area surrounding the historic downtown offers a charming experience that captures the essence of this coastal town. This neighborhood features a delightful mix of quaint shops, local eateries, and scenic views along the waterfront. One of the top attractions nearby is the Gloucester Museum of History, where you can delve into the rich heritage of the region. Additionally, the beautiful Ware River offers opportunities for kayaking and fishing, making it a great spot for outdoor enthusiasts.

Another attractive option is the area near the York River, which provides stunning views and easy access to parks and recreational activities. The nearby Yorktown Battlefield is a must-visit, showcasing the historical significance of the Revolutionary War. This area also boasts a variety of vacation rental properties, giving visitors a range of choices to suit different preferences and budgets.
How much does it cost to rent a vacation home in Gloucester?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Gloucester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Gloucester vacation house rentals?
You can find great discounts on house rentals in Gloucester on Vrbo, 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.
Where are the best areas for renting a beach house in Gloucester?
For renting a beach house in Gloucester, Virginia, the area around the Chesapeake Bay offers some delightful options. The stretch near Bethel Beach features picturesque properties that provide direct access to sandy shores and stunning bay views. Many of these rentals come equipped with amenities such as spacious decks for outdoor dining, fully stocked kitchens, and sometimes even private beach access, making them superb for families and groups looking to enjoy a coastal getaway.

Further along, the area around Ware River presents additional opportunities for beach house rentals. Here, you can find charming cottages that often include amenities like cozy fire pits, outdoor grills, and kayaks for exploring the serene waters. The proximity to local seafood restaurants and quaint shops in Gloucester Point also enhances the appeal, allowing travelers to enjoy both relaxation and local culture.

Additionally, the nearby historic district of Gloucester offers a great experience with its beautiful waterfront properties that combine modern comforts with historic charm. Many houses in this area feature large windows for soaking in the views, along with amenities like hot tubs and access to community docks.
What is the most popular type of vacation rental accomodation in Gloucester?
In Gloucester, vacation houses are the most popular rental choice, with around 15 available throughout the area. These homes typically provide spacious rooms, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces for enjoying the serene surroundings. The picturesque setting near the water makes them ideal for families or groups seeking a relaxing getaway. Additionally, there are about 11 cottages that offer a charming, cozy atmosphere, great for couples or smaller families looking for a quaint retreat. A few apartments and condos can also be found, providing convenient options for those wanting to stay closer to local amenities.
Are there any family house rentals in Gloucester?
In Gloucester, Virginia, there are numerous family-friendly vacation rentals available, with around 23 options scattered throughout the area. Visitors can find homes in neighborhoods that offer spacious layouts, great for family gatherings. Many of these properties come equipped with full kitchens, allowing families to prepare meals together, and comfortable living spaces where everyone can relax after a day of exploring.

Outdoor amenities such as decks or yards are common, providing a safe space for children to play. The proximity to local attractions like the historic Gloucester Court House, the scenic York River, and various parks makes this area ideal for family outings.
Can I rent a vacation home with a pool or hot tub in Gloucester?
In Gloucester, Virginia, there are several vacation homes available for rent that feature pools and hot tubs. This charming area, known for its scenic waterfront and historic sites, offers a peaceful retreat for travelers. Many of the rentals come with amenities such as private pools, hot tubs, and spacious outdoor areas, making them ideal for relaxation and family gatherings. Properties often include fully equipped kitchens, comfortable living spaces, and easy access to local attractions, ensuring a delightful stay in this picturesque setting.
Can I find long-stay vacation rentals in Gloucester?
A long-stay vacation rental in Gloucester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Gloucester?
In Gloucester, visitors can find a variety of pet-friendly house rentals that cater to travelers with furry companions. With around 13 options available, there are several charming properties scattered throughout the area. Many of these rentals feature spacious yards, allowing pets to roam freely, as well as amenities like fully equipped kitchens, outdoor grilling spaces, and cozy living areas for relaxation after a day of exploring.

The town is known for its scenic beauty, with waterfront properties often providing stunning views of the surrounding landscapes. Travelers can enjoy easy access to local parks and outdoor spaces where pets are welcome, making it a great destination for those looking to vacation with their animals.
Are there any remote work vacation rentals in Gloucester?
In Gloucester, Virginia, there are around 30 vacation rentals that are suitable for remote work. Many of these properties cater to professionals looking for a comfortable workspace while enjoying a getaway. Travelers can expect amenities such as dedicated desks, ergonomic chairs, and complimentary Wi-Fi, allowing for a productive work environment.

The area itself offers a charming blend of coastal scenery and historical sites, with points of interest like the historic Gloucester Courthouse and the picturesque York River. Many rentals are equipped with spacious living areas and full kitchens, providing a cozy atmosphere for both work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Gloucester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Gloucester with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Gloucester?
In Gloucester, Virginia, popular vacation rental amenities include well-equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals also feature decks or patios, providing outdoor spaces for relaxation and enjoying the scenic views of the surrounding area. Travelers can expect amenities like blenders and coffee/tea makers to enhance their experience, ensuring they can enjoy fresh beverages and quick meals. Onsite parking is commonly available, making it convenient for those traveling by car.
When is the best time to visit Gloucester for a vacation rental?
The best time to visit Gloucester for a vacation rental is during the lively summer months of June through August, with July being the most popular time to experience the area's charm. During this peak season, visitors can indulge in a variety of outdoor activities, such as kayaking in the picturesque rivers or enjoying leisurely days on the local beaches. The warm temperatures, typically ranging from the mid-70s to the low 90s Fahrenheit, create an inclusive setting for both relaxation and adventure.

As you explore Gloucester, you'll find that the vibrant community hosts numerous events, including festivals and local markets, all set against the backdrop of the scenic Chesapeake Bay. This is a fantastic time for travelers seeking both comfort and convenience, as many attractions and restaurants are fully operational and ready to cater to your needs.

For those looking to travel on a budget, consider visiting Gloucester in December. While it may be the low season, the area offers a unique charm with holiday festivities, beautiful decorations, and a quieter pace. This time can provide a cozy retreat and often more affordable rental options without sacrificing quality.

Ultimately, the best time to visit Gloucester will hinge on whether you prefer the bustling summer atmosphere filled with activities or the peaceful, festive feel of the winter season.
How early should I book a Gloucester vacation rental?
Book your Gloucester vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Gloucester, Virginia, United States of America?
In Gloucester, Virginia, visitors can explore a variety of attractions that highlight the area's rich history and natural beauty. The historic Gloucester Courthouse area features charming shops and restaurants, offering a glimpse into the town's past. Nearby, the Gloucester Museum of History provides insights into the county's heritage, showcasing artifacts and exhibits related to local history.

For nature enthusiasts, the beautiful landscapes of the Chesapeake Bay can be experienced at the nearby Beaverdam Park, which offers trails, fishing opportunities, and picnic areas. The park is an excellent spot for hiking and enjoying the scenic views of the water.

Additionally, visitors can explore the nearby York River State Park, which provides opportunities for kayaking, hiking, and observing local wildlife. The park's trails wind through diverse ecosystems, great for outdoor activities and appreciating the region's natural surroundings.
Can I change or cancel my Gloucester home rental booking on Vrbo?
To find Gloucester vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Gloucester vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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