Owner Direct Vacation
Rentals in Gloucester
The Best Owner Direct Vacation Rentals in Gloucester. Explore thousands of vacation home rentals, large cabins, and villas near Gloucester
GUESTS
Explore the Best Gloucester Vacation Homes
Looking for the perfect place to stay in Gloucester? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Gloucester character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
- Parking
- Accessibility
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- TV
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Parking
- Accessibility
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- View
- Ocean View
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Why Travelers Love Using
Owner Direct to
Find Gloucester Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Gloucester
- Parking
- Accessibility
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- TV
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- TV
Popular Neighborhoods for Gloucester Vacation Rentals
What are the best areas to stay in Gloucester
Discover the top neighborhoods in Gloucester and choose a place that suits your stay.
Monday Feb 9
Gloucester, Virginia
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Gloucester vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Gloucester
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- TV
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
How to Reserve Your Gloucester Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Gloucester Vacation Rental FAQs
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 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 vacation rentals are available in Gloucester?
Currently, the total number of properties listed in 2026 is over 47 in the Gloucester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Gloucester.