Gloucester vacation rentals

We found 495 vacation rentals — enter your dates for availability

Select from 19 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:Apr 3 - Apr 10

Image gallery for Fire Pit🔥 Walk to Town. 1st floor King Bed & Walk in Shower! Monthly Discounts!

Firepit in the backyard perfect for making smores & memories!
10 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)

Fire Pit🔥 Walk to Town. 1st floor King Bed & Walk in Shower! Monthly Discounts!

Mathews

8% off
Price is $227
$1,588 for 7 nights
All fees included
Fire Pit🔥 Walk to Town. 1st floor King Bed & Walk in Shower! Monthly Discounts!

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Find out more about Gloucester

Why visit Gloucester

  • Outdoor Adventures: Gloucester is perfect for nature lovers with its beautiful islands, relaxing beaches, and nearby parks for hiking and exploration.
  • Family-Friendly Activities: The area offers a variety of attractions that engage families, making it an ideal destination for all ages.
  • Charming Neighborhoods: Explore the scenic landscapes and quaint neighborhoods of Gloucester County, rich in history.
  • Affordable Accommodations: Enjoy a range of lodging options, from cozy cottages to luxurious rentals, suitable for every budget.
  • Warm Hospitality: Experience the friendly and welcoming nature of the locals during your stay.

Popular types of accommodation in Gloucester

Discover the charm of Gloucester with a variety of vacation rentals to suit every traveler. Whether you're looking for houses, cozy cottages, or modern condos, we have options that cater to your needs. From luxurious escapes to budget-friendly holiday cottages, finding the perfect place to stay is easy. Explore our selection of house rentals and VA houses for rent to make your Gloucester getaway unforgettable.

  • Houses: The top choice for visitors in Gloucester, offering spacious and comfortable stays ideal for families or groups.
  • Condos: A popular option for those seeking modern amenities and a community atmosphere during their stay in Gloucester.
  • Cottages: Charming and cozy, these rentals provide a quaint experience perfect for a relaxing getaway in Gloucester.
  • Cabins: Great for nature lovers, these rustic accommodations offer a unique experience in the scenic surroundings of Gloucester.
  • Apartments: Convenient and versatile, apartments are a favored choice for solo travelers or couples looking for a home-like feel.**

Top attractions in and around Gloucester

Gloucester, Virginia, is perfect for outdoor and family vacations, offering stunning scenery and a range of activities. Visitors can explore beautiful islands, relaxing beaches, and nearby national and state parks. Whether you're traveling with family or seeking a peaceful retreat, Gloucester provides a variety of attractions that cater to outdoor enthusiasts and beach lovers alike, making it an ideal destination for your next getaway.

  • Yorktown Beach: Experience the relaxing beach vibes at Yorktown Beach, located 12 miles from Gloucester. Enjoy the sandy shores, gentle waves, and stunning sunsets, perfect for a day of relaxation or a picnic with family and friends.
  • Rosewell Ruins: Step back in time at Rosewell Ruins, a historic site within Gloucester. Explore the remains of this once-grand plantation, immersing yourself in the rich cultural heritage and architectural beauty of the area.
  • Middle Peninsula State Park: Discover adventure at Middle Peninsula State Park, where outdoor enthusiasts can enjoy hiking, fishing, and picturesque scenery. The park offers a perfect escape for nature lovers seeking tranquility and breathtaking views.

Things to do recommended for couples

If you're seeking a romantic getaway in Gloucester, head to Williamsburg Winery, just 16 miles away. Enjoy wine tastings in a picturesque setting, perfect for couples. The ambiance is filled with romance and entertainment, making it an ideal spot to unwind and connect with each other.

Things to do recommended for families

Your family will have a blast at Water Country USA, a thrilling waterpark only 12 miles from Gloucester. For a more relaxed day, visit Brown Park or Waller Mill Park, both offering serene environments perfect for wellness and relaxation right in the area.

Things to do recommended for groups

Group travelers in Gloucester, Virginia can enjoy shopping at York River Crossing, just 9 miles away, or play a round of golf at Kiskiack Golf Club, 13 miles away, and Piankatank River Golf Club, located 10 miles away, both offering great outdoor sports vibes.

*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

If you’re traveling with friends, family, pets, or planning an extended stay, it’s important to use the right filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Gloucester with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor space for gatherings. Luckily, you can easily narrow down your options on Vrbo to find exactly what you need and more.
  • Traveling to Gloucester with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Gloucester: For many families, a trip wouldn't feel complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Gloucester: If you're in search of vacation rentals that offer discounts for stays of a month or more, 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 Gloucester

Gloucester, Virginia, offers a delightful blend of outdoor adventures and family-friendly activities, making it an ideal vacation spot. Explore the charming neighborhoods and scenic landscapes of Gloucester County, while also venturing nearby to historic Williamsburg. Enjoy affordable accommodations and experience the warm hospitality of friendly locals, all set against a backdrop rich in history and recreation. Whether you're in search of a relaxing getaway or an engaging family trip, Gloucester has something for everyone.

  • Schley: Schley is a charming village in Gloucester that offers a fantastic blend of outdoor adventure and family-friendly experiences. Nestled close to beautiful beaches and a national state park, Schley provides plenty of opportunities for hiking, picnicking, and enjoying nature. The local amusement park and recreation area are perfect for families, ensuring that everyone can find something fun to do. For those who enjoy shopping, the nearby shopping center offers a variety of options. Whether you're looking to explore historic sites or simply relax in the great outdoors, Schley is a delightful destination.
  • Zanoni: Zanoni is another picturesque village in Gloucester known for its stunning scenery and outdoor activities. Travelers flock to this area to appreciate its natural beauty, with nearby beaches, serene lakes, and nature reserves providing the perfect backdrop for exploration. Enjoy a day of education and fun at local attractions, including an amusement park and scenic boardwalk. The peaceful environment makes it ideal for picnics and leisurely strolls, making Zanoni a great choice for those looking for a tranquil yet adventurous getaway.
  • Ware Neck: Ware Neck is a delightful village that offers an array of outdoor activities and scenic views. Known for its beautiful golf courses, this area attracts golf enthusiasts from all around. The local shopping center provides a chance to explore unique shops and grab a bite to eat. Ware Neck is also close to stunning beaches, a national park, and a museum, making it a well-rounded destination for visitors. Whether you're hitting the greens or taking in the local history, Ware Neck is a fantastic spot for adventure and relaxation.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to better prices. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, be sure to utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer certainly has its perks. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use platform for planning your travel adventures. You can create new trips, continue from where you last stopped, or manage and view your itinerary all in one place. Your saved or booked properties will be neatly organized into categories like Potential, Upcoming, or Current Trips. To begin exploring 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)
  • Kiskiack Golf Club (12.6 mi / 20.3 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)

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:

  • Cuba Island (11.7 mi / 18.8 km)
  • Yorktown Beach (12 mi / 19.2 km)
  • White Stone Beach (16.8 mi / 27 km)
  • Newport News Park (17.6 mi / 28.4 km)
  • Greensprings Greenway Interpretative Trail (18.1 mi / 29.1 km)
  • Jamestown Beach (19.3 mi / 31 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 when booking a vacation rental?
When looking for the best area to stay in Gloucester, Virginia, consider the historic downtown area. This charming neighborhood offers a blend of quaint shops, cozy cafes, and rich history, making it an ideal spot for a vacation rental. The downtown area is also conveniently located near attractions such as the Gloucester Museum of History, where you can delve into the local heritage, and the picturesque Court House, which showcases stunning architecture and is a focal point of the community.

Another great option is the waterfront area, particularly along the banks of the York River. This scenic location provides beautiful views and opportunities for outdoor activities like fishing and kayaking. It's also close to popular points of interest such as the historic Ware Church and the serene Beaverdam Park, where you can enjoy hiking and birdwatching. In terms of vacation rentals, both the downtown and waterfront areas offer a diverse selection, ensuring you can find a property that suits your needs, whether you're looking for a cozy cottage or a spacious family home.
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, consider the picturesque waterfront areas along the York River and the Chesapeake Bay. The region near Gloucester Point offers charming vacation rentals with direct access to sandy beaches and beautiful views of the water. Many properties in this area feature amenities such as private docks for boating, spacious decks for outdoor entertaining, and fully equipped kitchens, great for families or groups seeking a relaxing getaway.

Further along the coast, the Mathews County area, which is just a short drive from Gloucester, provides additional options for beach house rentals. Here, you can find homes tucked away in tranquil settings, often with features like outdoor fire pits, screened porches, and cozy living areas. This area is ideal for travelers looking to enjoy both the beach and nearby nature reserves.

Additionally, the waterfront along the Rappahannock River offers opportunities for exploring local history and enjoying water activities. Rentals here frequently come with amenities such as kayaks, grills, and access to nearby parks with walking trails, making them suitable for those who appreciate both relaxation and adventure.
What is the most popular type of vacation rental accomodation in Gloucester?
In Gloucester, vacation houses are the most popular type of rental, with about 19 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for comfort and convenience. Additionally, there are around 13 cottages that provide a charming, rustic experience, often located near the waterfront or in peaceful settings surrounded by nature. Several apartments and condos can also be found, offering more compact accommodations for solo travelers or couples. Many of these rentals include outdoor spaces, like decks or patios, superb for enjoying the coastal breeze after a day of exploring local attractions such as the historic downtown or the scenic York River.
Are there any family house rentals in Gloucester?
In Gloucester, Virginia, families will be pleased to find a variety of rental homes—about 26 options available throughout the area. The picturesque surroundings make it an inviting destination for family gatherings. Many of these properties offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces ideal for children to play and explore. Common amenities such as Wi-Fi and air conditioning contribute to a comfortable stay.

The historic town center, with its charming shops and restaurants, is a short drive away, providing opportunities for local dining and cultural experiences. Furthermore, families can enjoy nearby outdoor activities, including water sports on the York River or visits to the scenic parks in the region.
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, providing a wonderful option for travelers looking to relax and unwind. The area is known for its scenic beauty along the waterways, making it an ideal destination for those who enjoy outdoor activities. Many rentals in Gloucester come equipped with amenities such as private pools, spacious outdoor areas for entertaining, and fully equipped kitchens, allowing guests to enjoy both relaxation and convenience during their stay. Additionally, some properties may offer features like fire pits and waterfront views, enhancing the overall experience.
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, travelers can find a variety of pet-friendly house rentals, with about 12 options available. Many of these properties are situated near the scenic waterfront, providing easy access to beautiful views and outdoor activities. Vacation rentals here often feature amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them ideal for families and groups traveling with pets.

The area around Gloucester Point is particularly appealing, with its proximity to parks and nature trails where pets can enjoy walks and playtime. Nearby, the historic downtown area offers charming shops and restaurants, ideal for visitors.
Are there any remote work vacation rentals in Gloucester?
In Gloucester, Virginia, there are numerous vacation rentals that cater to remote work needs, with around 36 options available. The area is known for its scenic waterfront, historical sites, and charming small-town atmosphere, making it an appealing place for those looking to blend work and leisure. Many of these properties come equipped with essential remote work amenities such as Wi-Fi, dedicated desks, ergonomic chairs, and even computer monitors, ensuring a productive environment during your stay.

Travelers can enjoy the tranquility of Gloucester while also having the opportunity to explore local attractions. The historic downtown area features quaint shops and restaurants, while the nearby York River offers stunning views and recreational activities. Additionally, the proximity to natural parks and waterfronts provides ample opportunities for relaxation and outdoor adventures after a day of work. 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, popular vacation rental amenities include kitchens, allowing guests to prepare their own meals with ease. Many rentals also provide WiFi, ensuring travelers can stay connected during their stay. For those who enjoy cooking, amenities like blenders are often available, great for whipping up smoothies or other creations. Additionally, many properties feature patios, offering outdoor space to relax and enjoy the pleasant Virginia weather. Coffee and tea makers are also commonly found, providing a convenient way to start the day with a warm beverage.
When is the best time to visit Gloucester for a vacation rental?
The best time to book a vacation rental in Gloucester is during the peak season from June to August. This vibrant period attracts families and outdoor enthusiasts looking to soak up the sun and enjoy the stunning waterfront views along the Chesapeake Bay. With warm temperatures averaging in the mid-80s Fahrenheit, Gloucester becomes a hub for water activities such as sailing, fishing, and kayaking, making it an ideal destination for those who appreciate both adventure and relaxation.

July stands out as the most popular month, offering a lively atmosphere with plenty of events and activities. Visitors can explore the local festivals that celebrate the area's rich maritime heritage, indulge in fresh seafood at waterfront restaurants, and take leisurely strolls along the scenic trails that wind through historic sites and natural beauty.

For travelers seeking a more budget-friendly option, visiting in December can be quite rewarding. While the temperatures dip to the low 40s Fahrenheit, the charm of Gloucester shines through with holiday festivities and cozy accommodations. This quieter month allows for a more intimate experience, where you can enjoy the local culture and festivities without the crowds.

Ultimately, the best time to visit Gloucester depends on whether you prefer the bustling summer months filled with activities or the peaceful atmosphere of winter, where you can enjoy the town's unique charm and hospitality.
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?
In Gloucester, Virginia, visitors can explore a variety of attractions that highlight the area's natural beauty and historical significance. The historic downtown area features charming shops and restaurants, superb for a leisurely stroll. Nearby, the Gloucester Museum of History offers insights into the region's past, including its maritime heritage.

For outdoor enthusiasts, the scenic Ware River provides opportunities for kayaking and fishing, while the adjacent Beaverdam Park is ideal for hiking and picnicking, featuring trails and a serene lake. Additionally, the area is known for its beautiful waterfront views, particularly at the Gloucester Point Beach Park, which offers a lovely spot for relaxation and scenic sunsets.

The surrounding countryside is dotted with wineries and farms, making it an excellent area for those interested in agritourism.
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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