Owner Direct Vacation
Rentals in Pickering
The Best Owner Direct Vacation Rentals in Pickering. Explore thousands of vacation home rentals, large cabins, and villas near Pickering
GUESTS
Explore the Best Pickering Vacation Homes
Looking for the perfect place to stay in Pickering? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Pickering 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
- Pet Friendly
- View
- Parking
- TV
- Balcony/Terrace
- Parking
- TV
- Balcony/Terrace
- Parking
- Balcony/Terrace
- Security/Safety
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- View
- Parking
- Pet Friendly
- View
- Parking
- Pet Friendly
- View
- Parking
- Pet Friendly
- Balcony/Terrace
- Parking
- Pet Friendly
- Balcony/Terrace
- Parking
- Pet Friendly
- Balcony/Terrace
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- View
- Parking
- TV
- Balcony/Terrace
- Parking
- TV
- Balcony/Terrace
- Parking
- Balcony/Terrace
- Security/Safety
Why Travelers Love Using
Owner Direct to
Find Pickering 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 Pickering
- Parking
- Pet Friendly
- View
- Parking
- TV
- Balcony/Terrace
- Parking
- TV
- Balcony/Terrace
- Parking
- Balcony/Terrace
- Security/Safety
Popular Neighborhoods for Pickering Vacation Rentals
What are the best areas to stay in Pickering
Discover the top neighborhoods in Pickering and choose a place that suits your stay.
Tuesday Feb 17
Pickering, England
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Pickering 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 Pickering
- Parking
- TV
- Balcony/Terrace
- Parking
- Pet Friendly
- Balcony/Terrace
- Parking
- Pet Friendly
- View
- Parking
- TV
- Balcony/Terrace
- Parking
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Balcony/Terrace
How to Reserve Your Pickering 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.
Pickering Vacation Rental FAQs
1. What are the top vacation rentals in Pickering?
There are a lot of options in Pickering. If you plan on staying in the Pickering area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pickering:
- Cawthorne House
- Lovely 3 Bedroom Cottage w/Garden, Thornton. Family&Bike Friendly. Parking Space
- Middlehead Cottages at Cropton Forest
- Bank Top Barn Double Bedroom Self-catering 2 guests
- Gorgeous Thornton-le-Dale 2 Bedroom Cottage & Garden, Cosy Family Friendly, WIFI
- 5 bedroom accommodation in Pickering
- Middlehead Huts at Cropton Forest
- Hungate Garden Cottage
- 3 bedroom accommodation in Pickering
- 1 bedroom accommodation in Thornton le Dale near Pickering
2. Which vacation homes in Pickering are best for families?
If you are looking for a family-friendly vacation home in Pickering, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pickering:
3. How many vacation rentals are available in Pickering?
Currently, the total number of properties listed in 2026 is over 598 in the Pickering area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pickering.