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

Pickering Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Pickering vacation homes

A stone house with a red-tiled roof, two visible windows, and a chimney.

1. Manor Cottage

Manor Cottage
4.0 star property
Pickering
The price is CA $712
CA $854 total
includes taxes & fees
Oct 14 - Oct 15
Manor Cottage
A hot tub on a wooden deck with stone walls and a tiled roof in the background.

2. 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 CA $3,765
CA $3,765 total
includes taxes & fees
Oct 12 - Oct 13
The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
A beach with rocks and people walking.

3. 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
A spacious loft with a high ceiling, exposed wooden beams, a kitchen area, and a staircase leading to an upper level.

4. 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 CA $273
CA $762 total
includes taxes & fees
Oct 15 - Oct 16
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
A living room with a beige sofa, a fireplace, a bookshelf, and framed artwork on the wall.

5. 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 CA $123
CA $148 total
includes taxes & fees
Oct 8 - Oct 9
Bedford House Retreat
A cozy living room with a fireplace, a television, and comfortable seating.

6. 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 CA $657
CA $748 total
includes taxes & fees
Oct 17 - Oct 18
Beautiful stone cottage in the heart of Helmsley - sleeps 2
A cozy living room with a brown leather sofa, a dining table with two chairs, a TV mounted on the wall, and a large window offering a view of the outdoors.

7. Thirley Beck Lodge

Thirley Beck Lodge
3.0 star property
Scarborough
The price is CA $455
CA $546 total
includes taxes & fees
Oct 16 - Oct 17
Thirley Beck Lodge
A stone building with a wooden bench outside, a door, and a sign that reads "The Barn".

8. This barn is a 1 bedroom(s), 1 bathrooms, located in Whitby, N Yorks.

This barn is a 1 bedroom(s), 1 bathrooms, located in Whitby, N Yorks.
Whitby
9.0 out of 10, Wonderful, (4 reviews)
"Nicely restored stone barn flat. Excellent communication from host Cara. 2 very friendly dogs bring treats for them.Excellent location for a coastal Moors holiday"
United States
Todd L.
The price is CA $360
CA $473 total
includes taxes & fees
Oct 8 - Oct 9
This barn is a 1 bedroom(s), 1 bathrooms, located in Whitby, N Yorks.
A living room with a sofa, two chairs, a table, and a lamp. There are two wall-mounted picture frames and a radiator.

9. 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 CA $189
CA $219 total
includes taxes & fees
Oct 7 - Oct 8
The Bungalow, Lingdale
A breakfast table with bread, croissants, and fruit, set on a yellow tablecloth.

10. Great location Holiday Home in Driffield

Great location Holiday Home in Driffield
Driffield
9.6 out of 10, Exceptional, (9 reviews)
"Beautiful house great base to explore Driffield from and our 2 year old slept so well."
United Kingdom
Anthony B.
The price is CA $160
CA $209 total
includes taxes & fees
Nov 1 - Nov 2
Great location Holiday Home in Driffield
A modern kitchen with a central island, bar stools, and a dining table set for two.

11. Meadowside Bungalow

Meadowside Bungalow
Weaverthorpe
The price is CA $645
CA $824 total
includes taxes & fees
Oct 11 - Oct 12
Meadowside Bungalow
A stone building with a red-tiled roof, multiple windows, and a paved driveway.

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

Sag Harbour, Sandsend Retreats at Saltmoore - Sag Harbour
Sandsend
The price is CA $319
CA $759 total
includes taxes & fees
Oct 7 - Oct 8
Sag Harbour, Sandsend Retreats at Saltmoore - Sag Harbour
A neatly arranged bedroom with a bed, pillows, a framed picture, a bedside lamp, and a shelf with a plant.

13. 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 CA $170
CA $283 total
includes taxes & fees
Oct 12 - Oct 13
Host & Stay | Grumbles Cottage
Room

14. Host Stay Harbour Cottage

Host Stay Harbour Cottage
2.0 star property
Saltburn-by-the-Sea
2.0 out of 10, (1 review)
"Cottage was ok but after booking through hotels.com I was contacted by Host & Stay and advised I had to pay an additional fee for a damage waiver. Alternatively I could pay a deposit but they take an admin fee so you don’t get the full amount back plus they state they may take 14 days to refund."
United Kingdom
Paul
The price is CA $143
CA $299 total
includes taxes & fees
Oct 8 - Oct 9
Host Stay Harbour Cottage
An outdoor seating area with a sofa and two chairs, a table with drinks, and a potted plant.

15. Hideaway

Hideaway
3.0 star property
Whitby
10.0 out of 10, Exceptional, (1 review)
"It was a lovely little cottage, had everything we could need. Staff were also very helpful. very comfortable place. We enjoyed our stay very much. However the mattresses were a bit hard but that made little difference. We still slept well 😊 would recommend! "
United Kingdom
Georgina
The price is CA $170
CA $355 total
includes taxes & fees
Oct 19 - Oct 20
Hideaway
A modern living room with a fireplace, a flat-screen TV, and a comfortable seating area.

16. The Sequoia

The Sequoia
3.0 star property
Scarborough
10.0 out of 10, Exceptional, (1 review)
"A lovely little cottage tucked away just outside Scarborough. We stayed over for a wedding and it was a convenient 10 minute drive to the registry office. The accommodation was well thought out with everything we needed. The hot tub was set up and ready to use as soon as we arrived, and even a chilled bottle of Prosecco waiting in the fridge!! The kids enjoyed themselves and especially liked watching the nesting swallows and meeting the resident horse in the stables. Great location, but...
United Kingdom
Sarah
The price is CA $675
CA $810 total
includes taxes & fees
Oct 10 - Oct 11
The Sequoia
A modern kitchen with grey cabinets, a built-in oven, and a sink.

17. 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 CA $129
CA $242 total
includes taxes & fees
Oct 15 - Oct 16
The Great Ayton Hideaway
A window with horizontal blinds, a view of buildings with red roofs, and a white wall.

18. Host & Stay | Harbour Cottage

Host & Stay | Harbour Cottage
Staithes
5.6 out of 10, (5 reviews)
"Newly refurbished to high standard. Being a 3 storey cottage space can be an issue and open plan steep stairs may be a problem for some. Location excellent. Would return."
United Kingdom
Garry C.
The price is CA $158
CA $253 total
includes taxes & fees
Oct 8 - Oct 9
Host & Stay | Harbour Cottage
A neatly made bed with pillows, a bedside table with a lamp, a mirror, and artwork on the wall.

19. Portman House

Portman House
Middlesbrough
The price is CA $104
CA $171 total
includes taxes & fees
Nov 5 - Nov 6
Portman House
A wooden deck with outdoor furniture, a stone building with a tiled roof, and a garden with red-leaved trees.

20. East Hampton, Sandsend Retreats at Saltmoore - East Hampton

East Hampton, Sandsend Retreats at Saltmoore - East Hampton
Whitby
The price is CA $319
CA $759 total
includes taxes & fees
Oct 19 - Oct 20
East Hampton, Sandsend Retreats at Saltmoore - East Hampton
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.
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Top Pickering Hotel Reviews

White Horse Farm Inn

White Horse Farm Inn

10/10 Excellent
"We had a one night stop here in October. The room had been redecorated reasonably recently, the bathroom also looked very modern, all very clean. A new mattress wouldn't go amiss though. The staff were very friendly and helpful, for our evening meal we had a pizza, which was ok, it was tasty and very filling. We didn't have breakfast so cant comment. The absolute best thing about this hotel is sitting outside the front having a drink and admiring a stunning view! That alone would bring us back. We will definitely return sometime, recommended."
James 1-night trip
Posted 10 hours ago
White Horse Farm Inn

Find out more about Pickering

Pickering Vacation Homes information

Number of reviews
75
Accommodation
44 Vacation Homes
Lowest Price
CA $148
Highest Price
CA $3,765