Book Holiday Homes in Pickering

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Pickering

Cottage in the  centre of Whitby - beautiful coastal and Abbey views

Cottage in the centre of Whitby - beautiful coastal and Abbey views

Whitby
Stay at this vacation home in Whitby. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. ...
Cottage in the centre of Whitby - beautiful coastal and Abbey views
Beach House "Just Beachy" Pool, Gym, Pet Friendly, close to Beach, WiFi, Netflix

Beach House "Just Beachy" Pool, Gym, Pet Friendly, close to Beach, WiFi, Netflix

Filey
Stay at this vacation home in Filey. Enjoy free WiFi, a fitness center, and an in-room coffeemaker. Popular attractions Reighton Sands and Hunmanby Sands are ...
Beach House "Just Beachy" Pool, Gym, Pet Friendly, close to Beach, WiFi, Netflix
Beach House Paradise Found WF-Fi, Netflix, Pool,Gym, Pet Friendly close to beach

Beach House Paradise Found WF-Fi, Netflix, Pool,Gym, Pet Friendly close to beach

Filey
Book a stay at this family-friendly vacation home in Filey. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Reighton Sands and Hunmanby ...
Beach House Paradise Found WF-Fi, Netflix, Pool,Gym, Pet Friendly close to beach
Save an average of 15% on thousands of hotels when you're signed in
Cottage in village location with lovely views to the Hambleton Hills and White H

Cottage in village location with lovely views to the Hambleton Hills and White H

York
Book a stay at this family-friendly vacation home in York. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Shandy Hall and Byland Abbey are ...
Cottage in village location with lovely views to the Hambleton Hills and White H
Beachfront Aparthotel, Seaview Apartment with free parking #2

Beachfront Aparthotel, Seaview Apartment with free parking #2

Redcar
The price is NZ$238 per night from 14 Apr to 15 Apr
NZ$238
includes taxes & fees
14 Apr - 15 Apr
Stay at this vacation home in Redcar. Enjoy air conditioning. Popular attractions Redcar Esplanade and Zetland Lifeboat Museum are located nearby.
Beachfront Aparthotel, Seaview Apartment with free parking #2
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.

Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.

York
Book a stay at this family-friendly vacation home in York. Enjoy free WiFi, a fitness center, and tennis courts. Popular attractions Redwood Park Fishing Lakes ...
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
Seadale Lodge- Holiday rental that sleeps 4-6 people with superb view of Filey

Seadale Lodge- Holiday rental that sleeps 4-6 people with superb view of Filey

Filey
Stay at this vacation home in Filey. Enjoy free WiFi, patios, and in-room fireplaces. Popular attractions West Avenue Pitch and Putt and Filey Beach are located ...
Seadale Lodge- Holiday rental that sleeps 4-6 people with superb view of Filey
Cottage With Sea Views

Cottage With Sea Views

Scarborough
Book a stay at this family-friendly vacation home in Scarborough. Enjoy free WiFi, a water park, and patios. Popular attractions Scarborough Open Air Theatre ...
Cottage With Sea Views
Rural peace & luxury near Malton, beautiful barn, stunning views, woodburner

Rural peace & luxury near Malton, beautiful barn, stunning views, woodburner

Malton
Stay at this vacation home in Malton. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Flamingo Land Theme Park and Zoo and Eden Camp ...
Rural peace & luxury near Malton, beautiful barn, stunning views, woodburner
Don't see what you're looking for?
See all available properties in Pickering
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pickering Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pickering vacation homes are the perfect way for you to wing it.

Holiday houses in Pickering let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pickering in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pickering adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pickering with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pickering vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Pickering Holiday Homes essential information

Accommodation
1233 Holiday Homes
Lowest Price
NZ$90
Highest Price
NZ$238
Popular accommodation
Cottage in the centre of Whitby - beautiful coastal and Abbey views , Beach House "Just Beachy" Pool, Gym, Pet Friendly, close to Beach, WiFi, Netflix, Beach House Paradise Found WF-Fi, Netflix, Pool,Gym, Pet Friendly close to beach, Cottage in village location with lovely views to the Hambleton Hills and White H, Beachfront Aparthotel, Seaview Apartment with free parking #2, Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym., Seadale Lodge- Holiday rental that sleeps 4-6 people with superb view of Filey, Cottage With Sea Views , Rural peace & luxury near Malton, beautiful barn, stunning views, woodburner

Top trending hotels in Pickering

The Royal Hotel

The Royal Hotel

3 out of 5
West Cliff, Whitby, England
Fully refundableReserve now, pay when you stay
The price is NZ$164 per night from 6 Apr to 7 Apr
NZ$164
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star hotel in Whitby. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
The Royal Hotel
Britannia Grand Hotel Scarborough

Britannia Grand Hotel Scarborough

3 out of 5
St. Nicholas Cliff, Scarborough, England
Fully refundableReserve now, pay when you stay
The price is NZ$90 per night from 6 Apr to 7 Apr
NZ$90
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star beach hotel in Scarborough. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the helpful staff and the clean rooms in ...
Britannia Grand Hotel Scarborough
Crown Spa Hotel Scarborough by Compass Hospitality

Crown Spa Hotel Scarborough by Compass Hospitality

4 out of 5
The Esplanade, Scarborough, England
Fully refundableReserve now, pay when you stay
The price is NZ$184 per night from 6 Apr to 7 Apr
NZ$184
includes taxes & fees
6 Apr - 7 Apr
Stay at this 4-star beach hotel in Scarborough. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
Crown Spa Hotel Scarborough by Compass Hospitality
Save an average of 15% on thousands of hotels when you're signed in
Penny Hedge, Whitby by Marston's Inns

Penny Hedge, Whitby by Marston's Inns

4 out of 5
Stainsacre Lane, Whitby, England
Fully refundableReserve now, pay when you stay
The price is NZ$172 per night from 5 May to 6 May
NZ$172
includes taxes & fees
5 May - 6 May
Stay at this 4-star inn in Whitby. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Penny Hedge, Whitby by Marston's Inns
Don't see what you're looking for?
See all available properties in Pickering
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.