Gloucester holiday lettings

We found 489 holiday rentals — enter your dates for availability

Select from 19 homes, 13 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:6 Mar - 13 Mar

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, (35 reviews)
Exceptional
(35 reviews)

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

Mathews, VA

8% off
Price is £1,182
for 7 nights, 1 home
£169 per night
includes taxes & fees
Fire Pit🔥 Walk to Town. 1st floor King Bed & Walk in Shower! Monthly Discounts!

Find spaces that suit your style

Why visit Gloucester

  • Stunning outdoor adventures: Enjoy a range of activities in Gloucester's beautiful parks, beaches, and islands, perfect for nature lovers and families alike.
  • Rich local heritage: Discover the area’s fascinating history through its charming communities and historical sites.
  • Family-friendly activities: Engage in a variety of activities that cater to visitors of all ages, ensuring fun for the whole family.
  • Charming accommodation options: Choose from delightful vacation homes, cosy cottages, and modern condos for a comfortable stay.
  • Relaxing atmosphere: Experience the serene vibe of Gloucester, ideal for unwinding and enjoying quality time with loved ones.

Popular types of accommodation in Gloucester

You've chosen Gloucester for your next getaway, and now it’s time to find the perfect accommodation. Explore a variety of options available, from charming houses and cosy cottages to modern condos. Whether you're seeking Gloucester rental listings, apartments in Gloucester County, or spacious homes, we have a range of choices to ensure a memorable stay in this picturesque locale.

  • Houses: The top choice for holidaymakers in Gloucester, these homes offer a perfect space for families or groups seeking comfort and privacy.
  • Condos: A popular option for those wanting modern amenities, condos provide a stylish and convenient base for exploring the area.
  • Cottages: These quaint and charming retreats are ideal for a peaceful getaway, nestled in picturesque surroundings.
  • Cabins: Perfect for nature enthusiasts, cabins offer a rustic escape while still being close to local attractions.
  • Flats: A practical choice for solo travellers or couples, flats provide essential comforts in a compact setting.**

Top attractions in and around Gloucester

Gloucester, Virginia, is ideal for outdoor and family holidays, offering a delightful blend of scenery and adventure. Visitors can explore stunning beaches, picturesque islands, and captivating state parks, making it a perfect destination for those seeking outdoor experiences and quality time with loved ones. With a variety of attractions to enjoy, Gloucester promises a memorable trip for all ages.

  • Yorktown Beach: A charming beach located 7.5km from Gloucester, Yorktown Beach offers a relaxing coastal atmosphere. Enjoy sunbathing, picnicking, or taking a leisurely stroll along the sandy shore while soaking in the picturesque views of the water.
  • Middle Peninsula State Park: Nestled within Gloucester, this national park is a haven for outdoor enthusiasts. Experience exhilarating adventures with hiking and wildlife watching, all set against stunning natural scenery.
  • Rosewell Ruins: These historic ruins provide a glimpse into the area's rich cultural heritage. Explore the remnants of this once-grand estate and appreciate the beautiful architecture and the stories it holds.

Things to do recommended for couples

If you're seeking a romantic getaway in Gloucester, the Williamsburg Winery is a must-visit, located 9.9km away. Enjoy the enchanting atmosphere, indulge in fine wines, and experience the local entertainment vibes for a perfect couple's retreat.

Things to do recommended for families

Families visiting Gloucester, Virginia, can have a splashing good time at Water Country USA, unwind at Waller Mill Park, or embark on an adventure at MagiQuest. Each destination is a short 7.5km from Gloucester, offering fun-filled experiences suitable for everyone.

Things to do recommended for groups

Enjoy a round of golf at Kiskiack Golf Club, just 8.1km from Gloucester, or savour craft beers at Alewerks Brewing Company, also 8.1km away. For a cultural experience, visit the Kimball Theatre, situated 8.7km from Gloucester, offering entertainment for all the family.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to set the right priorities when filtering your options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Gloucester with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Gloucester with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is advisable.
  • Taking your pets with you to Gloucester: For many, a family holiday isn’t quite the same without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Gloucester: If you're searching for holiday rentals offering discounts for stays of a month or more, you've come to the perfect place. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don’t forget to include additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay in Gloucester

Gloucester, Virginia, offers a delightful mix of outdoor adventures and family-friendly activities, making it an ideal holiday destination. Explore the picturesque surroundings, rich history, and welcoming communities in Gloucester County. Nearby, you’ll find charming neighbourhoods perfect for renters, along with a vibrant atmosphere that caters to both recreation and relaxation. Whether you’re enjoying scenic views or delving into local heritage, Gloucester promises a memorable experience for every visitor.

  • Zanoni: Zanoni is a picturesque village located in the Gloucester area, renowned for its stunning outdoor scenery and adventurous spirit. Visitors are drawn to the village for its remarkable natural beauty, with a nearby beach and lake perfect for relaxation and exploration. The local nature reserve offers a tranquil escape, while the amusement park and boardwalk provide delightful entertainment for families and thrill-seekers alike. Zanoni’s charming landscape and recreational opportunities make it an ideal destination for those seeking an adventurous getaway.
  • Ware Neck: Ware Neck is another delightful village situated within Gloucester, known for its scenic vistas and outdoor adventures. The area boasts a variety of engaging activities, including a well-maintained golf course that attracts enthusiasts from near and far. Shoppers will appreciate the local shopping centre, which offers a diverse range of shops and dining options. Close to the beach, national park, and museum, Ware Neck provides a perfect blend of relaxation and cultural exploration, making it a wonderful spot for tourists looking to immerse themselves in Virginia's natural beauty.
  • Schley: Schley is a charming village that promises outdoor fun and family-friendly experiences. The area is home to an amusement park and recreation park, making it a popular choice for families looking to enjoy a day of excitement. Nearby attractions include the beach, national state park, and theme park, providing ample opportunities for outdoor activities and exploration. Schley’s inviting atmosphere and array of attractions cater to visitors of all ages, ensuring a memorable holiday experience for everyone.

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that meets your budget, simply use our filters to sort by price, location, and type of holiday rental. We’re here to help you find the perfect accommodation for your needs.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up where you left off, or manage your travel arrangements with ease. You can now access the properties you've saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • 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 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)
  • White Stone Beach (16.8 mi / 27 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 a holiday rental in Gloucester, Virginia, a wonderful area to stay is the historic downtown district. This charming neighbourhood is steeped in history and offers a delightful blend of quaint shops, local eateries, and beautiful waterfront views along the York River. The area is particularly appealing for those who appreciate a relaxed atmosphere with easy access to attractions. One popular site is the Gloucester Museum of History, where visitors can delve into the rich past of the region. Additionally, the nearby Historic Court Circle showcases stunning architecture and is a lovely spot for leisurely strolls.

Another excellent choice is the area surrounding the Gloucester Point, which provides a stunning vantage point of the river and is within close proximity to the Virginia Institute of Marine Science. Here, you can enjoy outdoor activities such as fishing and boating, making it great for those who love nature and water sports. This neighbourhood tends to feature a good number of holiday rentals, suiting various preferences and budgets.
How much does it cost to rent a holiday home in Gloucester?
Prices for holiday 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 holiday 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, travellers should focus on the scenic waterfront areas along the York River and the Chesapeake Bay. The region offers a variety of properties that cater to different preferences, with many located near the charming historic district of Gloucester Courthouse, providing easy access to local shops and restaurants.

Along the riverfront, visitors can find spacious beach houses featuring amenities such as private docks, outdoor decks for entertaining, and fully equipped kitchens ideal for family gatherings. Many properties also boast direct access to the water, making activities like kayaking and fishing readily accessible.

Additionally, the area around the Gloucester Point Beach Park is particularly appealing for those looking for a more family-friendly atmosphere. Here, you can find beach house rentals that cater to larger groups, often equipped with amenities such as swimming pools, picnic areas, and fire pits, great for enjoying summer evenings. The park itself offers a sandy beach, playgrounds, and walking trails, enhancing the overall beachside experience.
What is the most popular type of holiday rental accomodation in Gloucester?
In Gloucester, holiday houses are the most popular type of rental accommodation, with around 19 available throughout the area. These houses typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups looking for a home-like environment. Additionally, there are about 12 charming cottages that offer a more rustic experience, often set in picturesque surroundings and equipped with essential amenities for a comfortable stay.
Are there any family house rentals in Gloucester?
In Gloucester, Virginia, there are a variety of family-friendly house rentals available, with around 26 properties to choose from. Visitors can find accommodations in neighbourhoods near the picturesque waterfront, providing easy access to activities along the York River. Many of these homes boast spacious living areas, full kitchens for preparing meals together, and outdoor spaces great for family gatherings and playtime.
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, providing excellent options for those looking to relax and unwind. The area is known for its picturesque waterfront and charming rural landscapes, making it a delightful destination for a getaway.
Can I find long-stay holiday rentals in Gloucester?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Gloucester?
In Gloucester, there are several pet-friendly house rentals available, with around twelve options for travellers to choose from. These holiday homes often come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets.
Are there any remote work holiday rentals in Gloucester?
In Gloucester, Virginia, there are a variety of remote work holiday rentals available, with around 35 options to choose from. This charming area offers a peaceful setting for those looking to balance work and leisure. Many of the properties are equipped with dedicated workspaces, including desks, ergonomic chairs, and high-speed Wi-Fi, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Gloucester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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, holiday rentals commonly feature essential amenities that cater to the needs of travellers. Most properties include a fully equipped kitchen, complete with a refrigerator, stovetop, microwave, and cookware, dishware, and utensils, allowing guests to prepare their meals comfortably. This focus on self-catering provides a convenient and homely atmosphere, ideal for families or groups looking to enjoy their stay in a more private setting.
When is the best time to visit Gloucester for a holiday rental?
The peak season for holiday rentals in Gloucester is during the summer months, specifically from June to August. This vibrant period attracts families and beach enthusiasts eager to enjoy the warm weather and the beautiful shoreline along the Chesapeake Bay. With temperatures soaring into the high 20s Celsius, visitors can indulge in a multitude of outdoor activities, including swimming, fishing, and kayaking, all while soaking in the stunning coastal scenery.

July stands out as the most popular month to visit Gloucester, drawing crowds with its lively atmosphere and numerous local festivals. Families can partake in events celebrating the region's rich maritime history, while outdoor enthusiasts can explore the nearby parks and nature trails. The long summer days provide ample opportunities for sightseeing and enjoying the picturesque waterfront.

For those looking for more budget-friendly options, consider visiting Gloucester in December. This quieter month offers a unique charm, as you can experience the festive season with holiday lights and local events, all while avoiding the hustle and bustle of peak tourist crowds. Embrace the crisp winter air with cozy walks along the waterfront or enjoy a warm drink at a local café.
How early should I book a Gloucester holiday rental?
Book your Gloucester holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Gloucester home rental booking on Vrbo?
To find Gloucester holiday 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 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 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, Vrbo 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 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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