Short-term rentals in Winchester
Winchester is the 80th-largest of 597 short-term rental markets across the United Kingdom: 1,043 listings, 73% on Airbnb. 16% of supply is run by professional operators, below the median market's 39%, led by Cottages.com (46 listings).
Data updated
- Tracked listings
- 1,043
- Market rank
- #80 / 597
- National share
- 0.2%
- Named professional operators
- 19
Airbnb vs Booking.com in Winchester
In Winchester, Airbnb leads with 758 listings (73%), 2.7× the 285 on Booking.com (27%).
Where the listings are in Winchester
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 Winchester
Booking.com supply is more professionalised than Airbnb's: 29% of Booking.com listings sit with operators of that size, against 10% on Airbnb. The 19 named professional operators run 124 local listings between them, and the three largest — Cottages.com, Forest Holidays and Sykes Holiday Cottages — account for 65% of that. The other 38 listings run by operators with 26 or more listings belong to operators without a published profile.
- Professional share
- 16%
- Median market
- 39%
- Single-listing hosts
- 46%
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 45% of Winchester's classified listings, followed by Apartments & flats (20%).
Largest operators in Winchester
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 | Cottages.com | 46 | 4.77 / 5 | 9.0 / 10 | 217,587 |
| 2 | Forest Holidays | 20 | 5.00 / 5 | — | 3 |
| 3 | Sykes Holiday Cottages | 14 | 4.70 / 5 | 8.9 / 10 | 179,990 |
| 4 | holidaycottages.co.uk | 9 | 4.73 / 5 | 8.9 / 10 | 73,474 |
| 5 | Pass the Property | 5 | 4.61 / 5 | 7.7 / 10 | 4,652 |
| 6 | Belvilla by OYO | 4 | 4.29 / 5 | 6.8 / 10 | 8,441 |
| 7 | HelloGuest Limited | 4 | 4.71 / 5 | 8.1 / 10 | 7,597 |
| 8 | ALSENED LTD | 3 | 3.45 / 5 | 6.4 / 10 | 152,134 |
| 9 | Curated Property | 3 | 4.81 / 5 | 8.2 / 10 | 4,668 |
| 10 | Finest Retreats | 3 | 4.64 / 5 | 8.5 / 10 | 13,960 |
The other 9 professional operators in Winchester
Local listings
- Travelnest Ltd 3 listings
- Host & Stay 2 listings
- The Cricketers Inn 2 listings
- Cumbrian Cottage Holidays 1 listing
- FabAccommodation 1 listing
- Hoseasons 1 listing
- Port Isaac Bay Holidays 1 listing
- Staybridge Suites 1 listing
- VanZyl 1 listing
Operators enter the index after reaching 26 listings across the United Kingdom and count Winchester among their markets. See the full interactive Winchester market report for additional filters and operator comparisons.
How Winchester compares
Winchester ranks 80th of 597 tracked markets in the United Kingdom, with 0.2% of tracked supply in this coverage. Markets of similar size:
-
Ipswich 1,051 listings
-
Southport 1,051 listings
-
Shrewsbury 1,045 listings
-
Pickering 1,042 listings
-
Stroud 1,042 listings
-
Brixham 1,032 listings
Photo credits
- Ipswich: Photo: Clear sky afternoon on the Ipswich Waterfront by LakeKnowledge · CC BY-SA 4.0 · cropped and resized for display, via Wikimedia Commons
- Southport: Photo: Lord Street, Southport by Small-town hero · Public domain · cropped and resized for display, via Wikimedia Commons
- Shrewsbury: Photo: The Square, Shrewsbury by Gnesener1900 · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons
- Pickering: Photo: Centre of Pickering by Charles Rispin · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Stroud: Photo: Stroud from the air by Air1jwilkins1212 · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons
- Brixham: Photo: Brixham from the sea by Kicior99 · CC BY 3.0 · cropped and resized for display, via Wikimedia Commons
Browse the full United Kingdom city directory or the United Kingdom market report .
Winchester market FAQ
How many short-term rentals are in Winchester?
Winchester has 1,043 short-term rental listings as of August 2026: 758 on Airbnb and 285 on Booking.com.
Who is the largest short-term rental operator in Winchester?
The largest professional operator in Winchester is Cottages.com, with 46 local listings.
How professionalised is the Winchester short-term rental market?
16% of Winchester's listings (162 of 1,043) are run by operators with 26 or more listings, below the median of 597 markets across the United Kingdom (39%). Booking.com supply is more professionalised than Airbnb's: 29% of Booking.com listings sit with operators of that size, against 10% on Airbnb. The 19 named professional operators run 124 local listings between them, and the three largest — Cottages.com, Forest Holidays and Sykes Holiday Cottages — account for 65% of that. The other 38 listings run by operators with 26 or more listings belong to operators without a published profile.
Is Airbnb or Booking.com bigger in Winchester?
In Winchester, Airbnb leads with 758 listings (73%), 2.7× the 285 on Booking.com (27%).
How many professional operators run listings in Winchester?
19 named professional operators run listings in Winchester. 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 1,043 public short-term rental listings in Winchester, 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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