Gloucester Rentals By Owner

Gloucester Rentals by Owner

Waterfront Farmhouse, Private Pool, Dock, 2 Master Suites - Book 8/26 - 9/1

Highly Rated

House

Waterfront Farmhouse, Private Pool, Dock, 2 Master Suites - Book 8/26 - 9/1

10.0

Exceptional

(77 Reviews)

4 Bedrooms 3 Baths 10 Guests 3000 ft²

£629/Night 7 Nights - £4,402

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Gloucester Retreat w/Backyard Oasis & Pier!

House

Gloucester Retreat w/Backyard Oasis & Pier!

9.5

Exceptional

(2 Reviews)

4 Bedrooms 3 Baths 10 Guests 2400.35 ft²

£380/Night 7 Nights - £2,663

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House

The Uncorked Cottage ~North River Retreat~North VA

10.0

Exceptional

(9 Reviews)

3 Bedrooms 3 Baths 7 Guests

£247/Night 7 Nights - £1,727

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Family-Friendly Main St Gloucester Apt w/Balcony!

Apartment

Family-Friendly Main St Gloucester Apt w/Balcony!

9.5

Exceptional

(2 Reviews)

2 Bedrooms 1 Bath 7 Guests 904.17 ft²

£177/Night 7 Nights - £1,242

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House

Water front Oasis with pickle-ball court and hot tub

8.8

Fabulous

(13 Reviews)

9 Bedrooms 7 Baths 22 Guests 3800 ft²

£844/Night 7 Nights - £5,910

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House

Radiant Gloucester House w/Private Porch!

9.4

Exceptional

(8 Reviews)

2 Bedrooms 1 Bath 6 Guests 1205.56 ft²

£96/Night 7 Nights - £671

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"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Highly Rated

House

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0

Exceptional

(117 Reviews)

2 Bedrooms 1 Bath 4 Guests 1000 ft²

£147/Night 7 Nights - £1,030

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Located in the Heart of Gloucester Courthouse!

New

House

Located in the Heart of Gloucester Courthouse!

3 Bedrooms 3 Baths 5 Guests 1700.7 ft²

£304/Night 7 Nights - £2,130

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Apartment

Eclectic Apartment- 2-4 friends- Family centered. Safe Neighborhood

10.0

Exceptional

(5 Reviews)

1 Bedroom 1 Bath 4 Guests

£130/Night 7 Nights - £913

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House

Private 2 BD 1 Bath Suite

10.0

Exceptional

(2 Reviews)

2 Bedrooms 1 Bath 4 Guests 940 ft²

£180/Night 7 Nights - £1,262

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Apartment

Family-Friendly Main St Gloucester Apt w/Balcony!

9.8

Exceptional

(7 Reviews)

2 Bedrooms 1 Bath 7 Guests 900 ft²

£253/Night 7 Nights - £1,768

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House

Radiant Gloucester House w/Private Porch!

9.4

Exceptional

(33 Reviews)

2 Bedrooms 1 Bath 6 Guests 1200 ft²

£191/Night 7 Nights - £1,339

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More Top-Rated Rentals by Owner in Gloucester Area

Why Choose Rent By Owner for your Gloucester vacation rental?

What makes our Rentals by Owner special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Gloucester

When should you plan your Rentals by Owner stay?

Finding the ideal time to vacation here can enhance your experience, allowing you to enjoy the region’s unique climate and seasonal offerings while making the most of your rental by owner booking in Gloucester, Virginia.

Peak Season Highlights

Spring (March to May)

During the spring months, you can enjoy pleasant weather and blooming landscapes, making it an ideal time to explore the region’s natural beauty from your rental by owner.

Average Temperature Daytime: around 65°F to 75°F - Nighttime: around 45°F to 55°F

Fall (September to November)

Autumn offers cooler temperatures and stunning fall foliage, perfect for outdoor activities and experiencing the area's vibrant seasonal colors from your vacation home.

Average Temperature Daytime: around 60°F to 70°F - Nighttime: around 40°F to 50°F

Off-Season Highlights

Summer (June to August)

In the summer, the region experiences warmer weather and longer days, providing a lively atmosphere suitable for outdoor adventures near your rental property.

Average Temperature Daytime: around 80°F to 90°F - Nighttime: around 60°F to 70°F

Winter (December to February)

During winter, the area tends to be quieter with cooler temperatures, offering a peaceful retreat and time to enjoy the cozy comfort of your vacation rental.

Average Temperature Daytime: around 40°F to 50°F - Nighttime: around 25°F to 35°F

Weekly Weather Forecast for Gloucester

How to Book Your Gloucester vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Gloucester

More Top-Rated Rentals by Owner in Gloucester Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy outdoor dining areas perfect for al fresco meals in the area’s pleasant climate.
Take advantage of spacious yards or gardens ideal for relaxing or outdoor activities.
Benefit from access to private patios or decks for enjoying the fresh air and scenic views.
Look for properties with fire pits or outdoor fireplaces to gather comfortably during cooler evenings.
Explore properties that feature outdoor grills, making it easy to host barbecues and cookouts.
Find rentals with covered porches or verandas that provide shaded spots to unwind outside.
Some accommodations offer boat docks or slip access for exploring the area’s waterways and lakes.

Top Attractions Around Gloucester

What attractions are nearby?

While staying here, you'll have the opportunity to explore a variety of nearby activities, including scenic outdoor adventures and cultural experiences that showcase the best of Gloucester's local charm.

Family Activities

Mariners Museum and Park: You can explore engaging maritime exhibits and enjoy outdoor activities along the riverwalk, making it a perfect family outing in this historic region.
Beacher’s Point Park: This scenic waterfront park offers picnic areas and gentle walking trails where your family can relax and take in the beautiful views of the area.
Historic District Tours: Discover the area's rich history through guided or self-guided tours that bring to life the stories of this destination's past.
Gloucester County Fairgrounds Events: Check out seasonal fairs and festivals held here, providing fun-filled entertainment for all ages during your stay.

Adult Activities

Historic Battlefields Tour: Explore the region's rich history by visiting notable battlefields that offer a glimpse into its historic significance.
Nature and Birdwatching at Local Parks: Enjoy peaceful walks and birdwatching opportunities in nearby parks that showcase the area's natural beauty.
Fishing and Boating on the River: Take advantage of the riverside amenities for fishing or boating adventures, perfect for relaxing days here.
Local Culinary Experiences: Savor regional flavors at local eateries that highlight the area's culinary heritage and provide a taste of this destination's charm.

Other Places to Stay in Gloucester, VA

Gloucester Travel Tips

How Can You Make the Most of Your Stay?

Explore local dining options: Take advantage of the area's diverse culinary scene to enjoy authentic regional flavors during your stay.
Visit nearby outdoor attractions: Make the most of the region’s natural beauty by exploring parks, trails, or waterfront areas close to your rental.
Immerse yourself in local history: Discover the area's rich heritage through museums and historic sites to enrich your visit.
Plan transportation ahead: Arrange for convenient travel options within the region to ensure smooth and stress-free exploration.

Transportation Options

Gloucester County Transit: Offers convenient bus services within the region, making it easy for you to explore local attractions without a car.
Rental Car Services: Numerous rental agencies operate in the area, providing reliable transportation options to suit your travel needs.
Taxi and Rideshare Options: Taxis and rideshare services like Uber and Lyft are readily available here, offering flexible ways to get around the destination.
Personal Vehicles: Having your own vehicle or renting one ensures freedom and ease when visiting specific sites across this scenic region.

Local Customs Options

Southern Hospitality: Expect warm welcomes and friendly interactions that reflect the region's renowned hospitality when you visit here.
The area's strong ties to maritime history influence local customs, including boat-related festivities and seafood delicacies.
Historic Preservation: Respect for historical sites and local heritage plays a significant role in community life and cultural events around this destination.
Community Festivals: Participating in local festivals offers a glimpse into regional pride and traditions unique to this part of Virginia.

Frequently Asked Questions About Gloucester Rentals by Owner

1. What are the top Vacation Rentals in Gloucester?

There are a lot of options in Gloucester. If you plan on staying in the Gloucester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Gloucester:

2. How many Vacation Rentals are available in Gloucester?

Currently, the total number of properties listed by RBO in 2026 is over 35 in the Gloucester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Gloucester. 

3. What is the cancellation policy for a rental by owner in Gloucester, Virginia?

The cancellation policy varies depending on the individual listing. You should review the specific terms provided on the rental's page or contact the owner directly to understand the conditions and any potential fees associated with cancellations.

4. How can I ensure the rental property in the region meets my needs before booking?

You can check the detailed property descriptions, photos, and amenities listed online. Additionally, reaching out to the owner for further questions or clarification helps ensure the rental aligns with your expectations.

5. Are there any additional fees I should be aware of when booking a private rental in this area?

Additional fees such as cleaning fees, service charges, or security deposits may apply. These details are typically specified in the listing, so review them carefully or ask the owner directly for clarity.

6. What steps should I take if I encounter issues during my stay in a rental property here?

First, contact the property owner promptly to address any concerns. If unresolved, consider reaching out to Rent By Owner's support team for assistance, ensuring your experience remains smooth and trustworthy.

7. Is it possible to modify my reservation after booking a rental by owner in Gloucester, Virginia?

Reservation modifications depend on the owner's policies. Contact the owner directly through the platform to request changes, and review the terms related to amendments or extensions before confirming.