Short-term rentals in Helmsley
Helmsley is the 255th-largest of 597 short-term rental markets across the United Kingdom: 620 listings, 58% on Airbnb. 56% of supply is run by professional operators, above the median market's 39%, led by holidaycottages.co.uk (97 listings).
Data updated
- Tracked listings
- 620
- Market rank
- #255 / 597
- National share
- 0.1%
- Named professional operators
- 14
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.
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 45% on Airbnb. The 14 named professional operators run 322 local listings between them, and the three largest — holidaycottages.co.uk, Cottages.com and Sykes Holiday Cottages — account for 81% of that. The other 27 listings run by operators with 26 or more listings belong to operators without a published profile.
- Professional share
- 56%
- Median market
- 39%
- Single-listing hosts
- 19%
Listings by operator portfolio size
Tracked listings grouped by how many properties their operator runs — from single hosts to 26+ professionals.
Listings by property type
Houses, cottages & holiday homes make up 82% of Helmsley's classified listings, followed by B&Bs & guest houses (7%).
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.
| # | Operator | Listings | Airbnb score | Booking.com score | Portfolio reviews |
|---|---|---|---|---|---|
| 1 | holidaycottages.co.uk | 97 | 4.73 / 5 | 8.9 / 10 | 73,474 |
| 2 | Cottages.com | 85 | 4.77 / 5 | 9.0 / 10 | 217,587 |
| 3 | Sykes Holiday Cottages | 80 | 4.70 / 5 | 8.9 / 10 | 179,990 |
| 4 | Norfolk Hideaways | 17 | 4.75 / 5 | 9.0 / 10 | 4,767 |
| 5 | WelcomeLets Yorkshire | 10 | 4.71 / 5 | 8.7 / 10 | 4,719 |
| 6 | Host & Stay | 8 | 4.57 / 5 | 8.3 / 10 | 59,134 |
| 7 | Yorkshire Escapes | 8 | 4.91 / 5 | — | 1,418 |
| 8 | Travelnest Ltd | 6 | 4.56 / 5 | 8.0 / 10 | 95,073 |
| 9 | Rural Retreats Holidays Ltd | 4 | 4.88 / 5 | 9.3 / 10 | 1,962 |
| 10 | Finest Retreats | 2 | 4.64 / 5 | 8.5 / 10 | 13,960 |
The other 4 professional operators in Helmsley
Local listings
- Norfolk Hideaways Ltd TA Yorkshire Hideaways 2 listings
- Crabtree & Crabtree 1 listing
- Ingrid Flute'S Yorks Hol Cottages 1 listing
- Port Isaac Bay Holidays 1 listing
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:
-
Porthleven 623 listings
-
Moffat 622 listings
-
Ballycastle 621 listings
-
Bourton on the Water 617 listings
-
Huddersfield 617 listings
-
Middlesbrough 617 listings
Photo credits
- Porthleven: Photo: Porthleven Harbour - geograph.org.uk - 218946 by Pam Brophy · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Moffat: Photo: Moffat from the hills by The original uploader was Robma at English Wikipedia . · CC BY-SA 2.5 · cropped and resized for display, via Wikimedia Commons
- Ballycastle: Photo: Ballycastle Harbour - geograph.org.uk - 468327 by Anne Burgess · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Bourton on the Water: Photo: Bourton-on-the-Water 2010 PD 09 by Bin im Garten · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons
- Huddersfield: Photo: Huddersfield Station by Tim Green · CC BY 2.0 · cropped and resized for display, via Wikimedia Commons
- Middlesbrough: Photo: Middlesbrough Town Hall, Yorkshire by Wikimedia Commons contributors · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons
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 August 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 97 local listings.
How professionalised is the Helmsley short-term rental market?
56% of Helmsley's listings (349 of 620) are run by operators with 26 or more listings, above the median of 597 markets across the United Kingdom (39%). Booking.com supply is more professionalised than Airbnb's: 72% of Booking.com listings sit with operators of that size, against 45% on Airbnb. The 14 named professional operators run 322 local listings between them, and the three largest — holidaycottages.co.uk, Cottages.com and Sykes Holiday Cottages — account for 81% of that. The other 27 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?
14 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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