Photo by Mark Stacevich

Search Holiday Homes in Pickering

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Pickering holiday homes

1. The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award

The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
Pickering
10.0 out of 10, Exceptional, (3 reviews)
"Eight friends (5 of whom were at uni together in the 70s) meet every year. Yorkshire was this year’s choice. We couldn’t have stayed in a better location. We loved everything: the house; the swim spa; the area; the weather. We would love to come back. Thank you!"
United Kingdom
Deborah H.
The price is £1,834
includes taxes & fees
9 Nov - 10 Nov
The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award

2. Manor Cottage

Manor Cottage
3.0 star property
Pickering
The price is £497
includes taxes & fees
11 Nov - 12 Nov
Manor Cottage

3. Luxury retreat for 2 couples/ family in spectacular location in North York Moors

Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Glaisdale
10.0 out of 10, Exceptional, (44 reviews)
"The property was excellent, beautiful throughout. We enjoyed our stay and the hosts were very welcoming and friendly. We would highly recommend "
United Kingdom
Catherine C.
The price is £408
includes taxes & fees
9 Nov - 10 Nov
Luxury retreat for 2 couples/ family in spectacular location in North York Moors

4. WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms

WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms
KIRBYMOORSIDE
WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms

5. 2-bed House Sleeps 4 - Private Garden - Pets Ok

2-bed House Sleeps 4 - Private Garden - Pets Ok
3.0 star property
Middlesbrough
The price is £114
includes taxes & fees
6 Dec - 7 Dec
2-bed House Sleeps 4 - Private Garden - Pets Ok

6. The Great Ayton Hideaway

The Great Ayton Hideaway
Great Ayton
8.0 out of 10, Very good, (1 review)
"Did what it said on the tin"
United Kingdom
Nick L.
The price is £126
includes taxes & fees
1 Dec - 2 Dec
The Great Ayton Hideaway

7. Bedford House Retreat

Bedford House Retreat
3.5 star property
Scarborough City Centre
8.0 out of 10, Very good, (3 reviews)
"Bedford House was amazing, the owners were fantastic, we had to change our dates at short notice they were very accommodating, thank you, we had a lovely 3 night stay and could have stayed longer, we were very lucky with the weather, we would absolutely recommend Bedford House but would not book through Hotels.com again, absolute nightmare of a company, when we tried to change our dates they told us that they could not do it as they could not contact the owners so we looked them up on their...
United Kingdom
Jackie
The price is £65
includes taxes & fees
15 Nov - 16 Nov
Bedford House Retreat

8. Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
10.0 out of 10, Exceptional, (1 review)
"Very happy with our stay. The accommodation was just right for 2, in a really excellent location"
United States
Helen H.
The price is £364
includes taxes & fees
8 Nov - 9 Nov
Beautiful stone cottage in the heart of Helmsley - sleeps 2

9. En-Suite Double with Parking · Walk to Whitby Abbey & 199 Steps

En-Suite Double with Parking · Walk to Whitby Abbey & 199 Steps
North Yorkshire
The price is £65
includes taxes & fees
24 Nov - 25 Nov
En-Suite Double with Parking · Walk to Whitby Abbey & 199 Steps

10. Thirley Beck Lodge

Thirley Beck Lodge
3.0 star property
Scarborough
The price is £318
includes taxes & fees
15 Nov - 16 Nov
Thirley Beck Lodge

11. Great location Holiday Home in Driffield

Great location Holiday Home in Driffield
Driffield
9.6 out of 10, Exceptional, (10 reviews)
"Beautiful house great base to explore Driffield from and our 2 year old slept so well."
United Kingdom
Anthony B.
The price is £117
includes taxes & fees
8 Nov - 9 Nov
Great location Holiday Home in Driffield

12. Host & Stay | Grumbles Cottage

Host & Stay | Grumbles Cottage
Whitby
8.0 out of 10, Very good, (3 reviews)
"Great little place, hosts were super quick at getting back to us and great at communicating. Loved the showers. No free parking close by however, so budget in some parking money. Also, 1st floor larger bed frame was wobbly, so favour the upstairs bedroom. Beautiful decor. Had everything we needed for a short stay."
United Kingdom
A W.
The price is £150
includes taxes & fees
8 Nov - 9 Nov
Host & Stay | Grumbles Cottage

13. Host Stay Grumbles Cottage

Host Stay Grumbles Cottage
2.0 star property
Whitby
The price is £186
includes taxes & fees
8 Nov - 9 Nov
Host Stay Grumbles Cottage

14. The Bungalow, Lingdale

The Bungalow, Lingdale
Lingdale
6.0 out of 10, (2 reviews)
"Does the job if you just need a place to sleep in the area but it needs some TLC and the garden is over grown, not sure if the heating is working. I'd hace still rated it as average as lomg as your not taking the family on holiday but communication feom the host was dreadful. I shluld have tp asl a half dozen times for access info, its not necessary and it adds to the stress. No one wants to make a three hour drive without knowing they will be able to get in when they get there "
United Kingdom
Michael
The price is £112
includes taxes & fees
8 Nov - 9 Nov
The Bungalow, Lingdale

15. 1 Bed Flat Sleeps 2 - Pets Welcome - Tv & Wifi

1 Bed Flat Sleeps 2 - Pets Welcome - Tv & Wifi
3.0 star property
Middlesbrough
The price is £86
includes taxes & fees
6 Dec - 7 Dec
1 Bed Flat Sleeps 2 - Pets Welcome - Tv & Wifi

16. Portman House

Portman House
Middlesbrough
The price is £95
includes taxes & fees
8 Nov - 9 Nov
Portman House

17. Meadowside Bungalow

Meadowside Bungalow
Weaverthorpe
The price is £418
includes taxes & fees
8 Nov - 9 Nov
Meadowside Bungalow

18. Millers Terrace - Luxury 3 Bed, Sleeps 6

Millers Terrace - Luxury 3 Bed, Sleeps 6
Whitby
The price is £219
includes taxes & fees
8 Nov - 9 Nov
Millers Terrace - Luxury 3 Bed, Sleeps 6

19. Glasswing Stays | Scoresby Cottage.

Glasswing Stays | Scoresby Cottage.
North Yorkshire
The price is £277
includes taxes & fees
18 Nov - 19 Nov
Glasswing Stays | Scoresby Cottage.

20. Sag Harbour, Sandsend Retreats at Saltmoore - Sag Harbour

Sag Harbour, Sandsend Retreats at Saltmoore - Sag Harbour
Sandsend
The price is £403
includes taxes & fees
9 Nov - 10 Nov
Sag Harbour, Sandsend Retreats at Saltmoore - Sag Harbour
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.

Learn more about Pickering

Step aboard the North Yorkshire Moors Railway for a nostalgic steam train journey through spectacular countryside. Explore the medieval castle ruins and discover local heritage at the Beck Isle Museum with its Victorian-era workshops and displays.

A stone castle ruin with a flag on top, surrounded by green grass and trees.
Photo by Mark Stacevich
Open Photo by Mark Stacevich

Top reviews in Pickering

Explore a world of travel with Expedia