myDataValue

Short-term rentals in Helmsley

Helmsley has 620 tracked short-term rental listings in myDataValue's November 2026 snapshot, 359 on Airbnb and 261 on Booking.com. That ranks it 255th of 597 short-term rental markets across the United Kingdom, with 58% of its listings on Airbnb. 59% of supply is run by professional operators, above the median market's 41%, led by holidaycottages.co.uk (101 listings). Counts are tracked public listings, not total supply.

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View of Helmsley
Photo: Rj helmsley by Mr R Jordan ( Mr R Jordan ) · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons

Data updated

Tracked listings
620
Market rank
#255 / 597
National share
0.1%
Named professional operators
12

Airbnb vs Booking.com in Helmsley

In Helmsley, Airbnb leads with 359 listings (58%), versus 261 on Booking.com (42%).

Where the listings are in Helmsley

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 620 tracked listings — open the full interactive report

Market structure in Helmsley

Booking.com supply is more professionalised than Airbnb's: 72% of Booking.com listings sit with operators of that size, against 49% on Airbnb. The 12 named professional operators run 334 local listings between them, and the three largest — holidaycottages.co.uk, Cottages.com and Sykes Holiday Cottages — account for 80% of that. The other 31 listings run by operators with 26 or more listings belong to operators without a published profile.

Professional share
59%
Median market
41%
Single-listing hosts
18%

Listings by operator portfolio size

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

  • Single listing 110
  • 2–5 listings 101
  • 6–25 listings 44
  • 26+ (professional) 365

Listings by property type

Houses, cottages & holiday homes make up 82% of Helmsley's classified listings, followed by B&Bs & guest houses (7%).

  • Houses, cottages & holiday homes 505
  • B&Bs & guest houses 45
  • Unique & outdoor 29
  • Hotels & hostels 19
  • Apartments & flats 18
  • Other 2
  • Private & shared rooms 2

Largest operators in Helmsley

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 Helmsley, ranked by local tracked listings.
# Operator Listings Airbnb score Booking.com score Portfolio reviews
1 holidaycottages.co.uk 101 4.73 / 5 8.8 / 10 82,888
2 Cottages.com 85 4.77 / 5 9.0 / 10 221,687
3 Sykes Holiday Cottages 81 4.69 / 5 8.9 / 10 184,961
4 Norfolk Hideaways 20 4.75 / 5 9.0 / 10 4,836
5 NORTH YORKSHIRE COTTAGE HOLIDAYS LTD 18 4.72 / 5 8.7 / 10 492
6 Host & Stay 9 4.57 / 5 8.3 / 10 59,959
7 Yorkshire Escapes 8 4.91 / 5 — 1,508
8 Rural Retreats Holidays Ltd 4 4.88 / 5 9.3 / 10 2,036
9 Travelnest Ltd 4 4.52 / 5 8.0 / 10 99,168
10 Finest Retreats 2 4.65 / 5 8.5 / 10 14,946

The other 2 professional operators in Helmsley

Local listings

Browse the full United Kingdom operator directory →

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

How Helmsley compares

Helmsley ranks 255th of 597 tracked markets in the United Kingdom, with 0.1% 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 .

Helmsley market FAQ

How many short-term rentals are in Helmsley?

Helmsley has 620 short-term rental listings as of November 2026: 359 on Airbnb and 261 on Booking.com.

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

The largest professional operator in Helmsley is holidaycottages.co.uk, with 101 local listings.

How professionalised is the Helmsley short-term rental market?

59% of Helmsley's listings (365 of 620) 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: 72% of Booking.com listings sit with operators of that size, against 49% on Airbnb. The 12 named professional operators run 334 local listings between them, and the three largest — holidaycottages.co.uk, Cottages.com and Sykes Holiday Cottages — account for 80% of that. The other 31 listings run by operators with 26 or more listings belong to operators without a published profile.

Is Airbnb or Booking.com bigger in Helmsley?

In Helmsley, Airbnb leads with 359 listings (58%), versus 261 on Booking.com (42%).

How many professional operators run listings in Helmsley?

12 named professional operators run listings in Helmsley. 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 620 public short-term rental listings in Helmsley, 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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