Best Vacation Homes in Gloucester
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $260/Night
For 7 Nights CA $1,821
2400.35 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Parking
- Internet
- Child Friendly
CA $850/Night
For 7 Nights CA $5,949
1 Bedroom
1 Bathroom
Ocean View
RV Rental
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $217/Night
For 7 Nights CA $1,521
1500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $398/Night
For 7 Nights CA $2,786
1194.79 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
CA $177/Night
For 7 Nights CA $1,240
900 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $197/Night
For 7 Nights CA $1,380
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $205/Night
For 7 Nights CA $1,434
850 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $197/Night
For 7 Nights CA $1,381
Gloucester Luxury Rentals
3800 ft²
22 Guests
9 Bedrooms
7 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $1,992/Night
For 7 Nights CA $13,945
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $876/Night
For 7 Nights CA $6,132
3000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Other
- Private Pool
- Fireplace/Heating
- Pool
CA $807/Night
For 7 Nights CA $5,649
2400 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $714/Night
For 7 Nights CA $4,998
2549 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $578/Night
For 7 Nights CA $4,048
2200 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $566/Night
For 7 Nights CA $3,960
900 ft²
7 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $395/Night
For 7 Nights CA $2,763
7 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $391/Night
For 7 Nights CA $2,736
Gloucester Pet Friendly Vacation Rentals
1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $287/Night
For 7 Nights CA $2,008
904.17 ft²
7 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Spa
- Fireplace/Heating
- Pet Friendly
CA $328/Night
For 7 Nights CA $2,296
7 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $320/Night
For 7 Nights CA $2,244
349.06 ft²
20 Guests
79 Bedrooms
7 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $186/Night
For 7 Nights CA $1,301
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $370/Night
For 7 Nights CA $2,594
2300 ft²
9 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $484/Night
For 7 Nights CA $3,391
Gloucester Large Vacation Homes
1450 ft²
10 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $280/Night
For 7 Nights CA $1,959
3200 ft²
10 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
CA $995/Night
For 7 Nights CA $6,965
1500 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $362/Night
For 7 Nights CA $2,537
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Other
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $291/Night
For 7 Nights CA $2,035
Why Choose Rent By Owner for your Gloucester Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals stay?
Choosing the right time to visit this charming destination ensures you can enjoy its unique atmosphere and make the most of your stay in Gloucester, Virginia, USA.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the region experiences warm weather and longer days, making it ideal for enjoying outdoor activities and exploring local attractions.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Early Fall (September to October)
This period offers pleasant temperatures and fewer crowds, perfect for relaxing and taking in the natural beauty of the area.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
The cooler months bring cooler temperatures and quieter surroundings, providing a peaceful retreat for those seeking tranquility away from the peak travel times.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Late Fall to Early Winter (November)
As the leaves fall and temperatures drop, you can enjoy a quieter visit with the opportunity for cozy stays and scenic views without larger crowds.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F
Weekly Weather Forecast for Gloucester
How to Book Your Gloucester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Gloucester
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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 access to spacious outdoor seating areas perfect for relaxing and entertaining.
- Take advantage of private or shared grilling stations to prepare meals surrounded by scenic views.
- Discover well-maintained lawns or gardens that add to the tranquil atmosphere of your stay.
- Make use of outdoor fire pits for cozy evenings under the stars with family or friends.
- Explore nearby walking trails or nature paths that showcase the natural beauty of the region.
- Utilize outdoor recreational equipment such as kayaks, paddleboards, or bicycles if available.
- Relax in inviting patios or verandas that offer picturesque views of the surrounding landscape.
Top Attractions Around Gloucester
What attractions are nearby?
In this charming destination, you can explore a variety of outdoor activities, historical sites, and cultural attractions that highlight the unique character of the region, making it an ideal spot for your next getaway.
Family Activities
- Historic Gloucester County Tour: Discover the rich history of the area by exploring local museums and landmarks that offer engaging insights into its past.
- Potomac River Waterfront Activities: Enjoy family-friendly activities such as fishing, kayaking, or simply relaxing along the scenic riverfront in this region.
- Natural Trail Exploration: Embark on a hike or nature walk through protected parks and trails that showcase the area's diverse wildlife and beautiful landscapes.
- Farmers Market Visits: Experience local flavors and pick up fresh produce at bustling farmers markets that highlight the region’s agricultural heritage.
Adult Activities
- Exploring historic sites: You can immerse yourself in the region’s rich history by visiting well-preserved landmarks and museums that tell the story of Gloucester’s past.
- Enjoying outdoor recreation: The area offers a variety of outdoor activities such as boating, fishing, and hiking that allow you to appreciate its scenic natural beauty.
- Savoring local cuisine: Indulge in the region’s culinary scene by trying out local restaurants known for their fresh seafood and regional specialties.
- Visiting cultural events: Take advantage of seasonal festivals and community events organized within this destination, providing authentic experiences and entertainment.
Other Places to Stay in Gloucester, VA
Rosewell Ruins
Schley
Ware Neck
Zanoni
Gloucester Museum of History
Riverside Walter Reed Hospital
Gloucester County
Petsworth
Gloucester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take time to discover the area's unique historical sites and outdoor activities that highlight Gloucester's rich heritage and natural beauty.
- Plan Ahead for Dining: Research local eateries and specialized cuisine options nearby to make dining experiences both convenient and memorable.
- Utilize Nearby Amenities: Make the most of nearby shopping centers, parks, and community events to enrich your stay in this region.
- Schedule Outdoor Adventures: Take advantage of the area's scenic spots and outdoor recreation opportunities for a relaxing and engaging vacation experience.
Transportation Options
- Virginia Railway Express (VRE): This commuter rail service offers convenient transportation into nearby urban centers, making it easy to explore the region from your vacation rental.
- Local Bus Services: Local bus routes provide affordable and accessible transit options within the area, connecting you seamlessly to key destinations around your stay.
- Taxi and Rideshare Services: Taxis and rideshare options such as Uber and Lyft are readily available, offering flexible transportation for trips within Gloucester County and beyond.
- Private Car Rentals: Renting a car locally allows you to explore the scenic surroundings and nearby attractions at your own pace during your visit here.
Local Customs Options
- Traditional Seafood Cuisine: You’ll find that seafood is a cornerstone here, with local customs emphasizing fresh catches prepared in time-honored ways that reflect the area's maritime heritage.
- Historic Civil War Commemoration: Visiting during special events allows you to observe respectful reenactments and ceremonies that honor the region’s significant role in American history.
- Southern Hospitality and Community Gatherings: Expect warm welcomes and community-centered events where friendly locals celebrate regional traditions and foster a sense of belonging.
Frequently Asked Questions About Gloucester?
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:
- Historic Cottage on Ware River Estate
- Relax, Refresh, Renew.Waterfront Cottage.Near Williamsburg
- Charming Quiet Retreat on North River in Historic Gloucester, Virginia
- "Bee Haven" Cottage Retreat Near Colonial Williamsburg
- Waterfront Farmhouse, Private Pool, Dock, 2 Master Suites + optional guesthouse
- Welcome to "The Happy Soul"
- Welcome to this Waterfront Home with Amazing Viewsn
- Right on Main St! Shops, Arts, Dining and More!
- Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock
- The Uncorked Cottage ~North River Retreat~North VA
2. How many vacation rentals have private pools in Gloucester?
There are 1 vacation rentals with private pools near Gloucester. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Gloucester are best for families?
If you are looking for a family-friendly vacation home in Gloucester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Gloucester:
4. How many Rentbyowner vacation rentals are available in Gloucester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 47 in the Gloucester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Gloucester.
5. What is the cancellation policy for vacation rentals in Gloucester, Virginia?
Cancellation policies vary depending on the property owner’s terms listed on the booking platform. It is recommended to carefully review the specific policies for your selected property in this destination before confirming your reservation.
6. Are there any additional fees associated with booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or local taxes may apply and are detailed within each property listing. To avoid surprises, review all fees specified before finalizing your booking.
7. How do I contact the property owner if I have questions about my stay?
You can reach out directly through the messaging system provided on the booking platform. The property owner’s contact information is usually available to help address any specific inquiries regarding your stay in this region.
8. What amenities are typically included in vacation rentals in this area?
Most listings feature essential amenities like Wi-Fi, kitchens, and parking. For additional features such as pools, outdoor spaces, or pet accommodations, consult the detailed property description and amenities list on the listing.
9. Is it possible to modify or extend my reservation after booking in Gloucester, Virginia?
Reservation modifications depend on the property owner’s policies and availability. Contact the owner directly through the platform to discuss any changes or extensions to your planned stay in this destination.
Gloucester Top Rated Vacation Rentals
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Private Pool
- Pool
- Balcony/Terrace
CA $194/Night
For 7 Nights CA $1,356
CA $159/Night
For 7 Nights CA $1,114
719.64 ft²
28 Guests
83 Bedrooms
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
CA $207/Night
For 7 Nights CA $1,448
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
CA $134/Night
For 7 Nights CA $938
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
CA $558/Night
For 7 Nights CA $3,905
2300 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $461/Night
For 7 Nights CA $3,225
700 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
CA $330/Night
For 7 Nights CA $2,313
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Spa
- Fireplace/Heating
- Pool
CA $246/Night
For 7 Nights CA $1,726
