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Short-term rentals in Pickering

Pickering has 1,042 tracked short-term rental listings in myDataValue's November 2026 snapshot, 622 on Airbnb and 420 on Booking.com. That ranks it 81st of 597 short-term rental markets across the United Kingdom, with 60% of its listings on Airbnb. 63% of supply is run by professional operators, above the median market's 41%, led by Cottages.com (230 listings). Counts are tracked public listings, not total supply.

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Photo: Centre of Pickering by Charles Rispin · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons

Data updated

Tracked listings
1,042
Market rank
#81 / 597
National share
0.2%
Named professional operators
13

Airbnb vs Booking.com in Pickering

In Pickering, Airbnb leads with 622 listings (60%), versus 420 on Booking.com (40%).

Where the listings are in Pickering

The dots are a representative sample of tracked short-term rentals — Airbnb in red and Booking.com in blue. Zoom and pan to explore the market, or open the full report for filters, operator overlays, and the listing-level view.

Airbnb Booking.com 250 sampled locations from 1,042 tracked listings — open the full interactive report

Market structure in Pickering

Booking.com supply is more professionalised than Airbnb's: 70% of Booking.com listings sit with operators of that size, against 58% on Airbnb. The 13 named professional operators run 563 local listings between them, and the three largest — Cottages.com, Sykes Holiday Cottages and holidaycottages.co.uk — account for 89% of that. The other 93 listings run by operators with 26 or more listings belong to operators without a published profile.

Professional share
63%
Median market
41%
Single-listing hosts
14%

Listings by operator portfolio size

Tracked listings grouped by how many properties their operator runs — from single hosts to 26+ professionals.

  • Single listing 151
  • 2–5 listings 157
  • 6–25 listings 78
  • 26+ (professional) 656

Listings by property type

Houses, cottages & holiday homes make up 81% of Pickering's classified listings, followed by Private & shared rooms (5%).

  • Houses, cottages & holiday homes 841
  • Private & shared rooms 54
  • Apartments & flats 52
  • Unique & outdoor 49
  • B&Bs & guest houses 40
  • Hotels & hostels 6

Largest operators in Pickering

Ranked by local tracked listings across Airbnb and Booking.com. Scores and portfolio review totals are aggregated across each operator's tracked United Kingdom listings. Together, the table and directory cover every professional operator we track in this market.

Scroll sideways to see all columns.

Largest operators in Pickering, ranked by local tracked listings.
# Operator Listings Airbnb score Booking.com score Portfolio reviews
1 Cottages.com 230 4.77 / 5 9.0 / 10 221,687
2 Sykes Holiday Cottages 192 4.69 / 5 8.9 / 10 184,961
3 holidaycottages.co.uk 77 4.73 / 5 8.8 / 10 82,888
4 Host & Stay 40 4.57 / 5 8.3 / 10 59,959
5 NORTH YORKSHIRE COTTAGE HOLIDAYS LTD 10 4.72 / 5 8.7 / 10 492
6 Travelnest Ltd 3 4.52 / 5 8.0 / 10 99,168
7 Finest Retreats 2 4.65 / 5 8.5 / 10 14,946
8 Norfolk Hideaways 2 4.75 / 5 9.0 / 10 4,836
9 Port Isaac Bay Holidays 2 4.84 / 5 9.1 / 10 138,199
10 The Holiday Cottage Collection 2 4.74 / 5 8.7 / 10 1,076

The other 3 professional operators in Pickering

Local listings

Browse the full United Kingdom operator directory →

Operators enter the index after reaching 26 listings across the United Kingdom and count Pickering among their markets. See the full interactive Pickering market report for additional filters and operator comparisons.

How Pickering compares

Pickering ranks 81st of 597 tracked markets in the United Kingdom, with 0.2% of tracked supply in this coverage. Markets of similar size:

Photo credits

Browse the full United Kingdom city directory or the United Kingdom market report .

Pickering market FAQ

How many short-term rentals are in Pickering?

Pickering has 1,042 short-term rental listings as of November 2026: 622 on Airbnb and 420 on Booking.com.

Who is the largest short-term rental operator in Pickering?

The largest professional operator in Pickering is Cottages.com, with 230 local listings.

How professionalised is the Pickering short-term rental market?

63% of Pickering's listings (656 of 1,042) are run by operators with 26 or more listings, above the median of 597 markets across the United Kingdom (41%). Booking.com supply is more professionalised than Airbnb's: 70% of Booking.com listings sit with operators of that size, against 58% on Airbnb. The 13 named professional operators run 563 local listings between them, and the three largest — Cottages.com, Sykes Holiday Cottages and holidaycottages.co.uk — account for 89% of that. The other 93 listings run by operators with 26 or more listings belong to operators without a published profile.

Is Airbnb or Booking.com bigger in Pickering?

In Pickering, Airbnb leads with 622 listings (60%), versus 420 on Booking.com (40%).

How many professional operators run listings in Pickering?

13 named professional operators run listings in Pickering. The full roster is listed on this page, and the interactive market report maps every listing.

About this data

Figures come from myDataValue's cross-platform market snapshot of 1,042 public short-term rental listings in Pickering, matching Airbnb and Booking.com supply to the operators who run it. Operators enter the index after reaching 26 listings on Airbnb or Booking.com across the United Kingdom. Snapshot dates: Airbnb , Booking.com .

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