Short-term rentals in Winchester
Local supply skews to Airbnb, with 3.1× the Booking.com inventory. Its largest professional operator, Cottages.com, runs 43 listings locally.
Explore the interactive Winchester report
Data updated
- Tracked listings
- 1,049
- Market rank
- #102 / 598
- National share
- 0.2%
- Professional operators
- 20
Listing mix by platform in Winchester
Where the listings are in Winchester
The dots are a representative sample of tracked short-term rentals — Airbnb in red, Booking.com in blue. Zoom and pan here, or open the full report for filters, operator overlays, and the listing-level view.
What the Winchester short-term rental supply looks like
Listings by property type
How Winchester's tracked listings split across property types on each platform.
Listings by operator portfolio size
Tracked listings grouped by how many properties their operator runs — from single hosts to 26+ professionals.
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 | 43 | 4.76 / 5 | 9.0 / 10 | 184,368 |
| 2 | Forest Holidays | 20 | 4.92 / 5 | — | 14 |
| 3 | Sykes Holiday Cottages | 14 | 4.67 / 5 | 8.9 / 10 | 131,996 |
| 4 | Holidaycottages.Co.Uk | 11 | 4.73 / 5 | 8.9 / 10 | 35,230 |
| 5 | Ava And Team | 7 | 4.20 / 5 | 7.5 / 10 | 24,516 |
| 6 | Prestige Holiday | 5 | — | 8.5 / 10 | 37,856 |
| 7 | Pass The Property | 4 | 4.59 / 5 | 8.1 / 10 | 4,316 |
| 8 | Curated Property | 2 | 4.82 / 5 | 8.5 / 10 | 4,477 |
| 9 | Finest Retreats | 2 | 4.60 / 5 | 8.6 / 10 | 9,583 |
| 10 | HelloGuest Limited | 2 | — | 8.1 / 10 | 2,817 |
All 20 professional operators in Winchester
- Cottages.com (43)
- Forest Holidays (20)
- Sykes Holiday Cottages (14)
- Holidaycottages.Co.Uk (11)
- Ava And Team (7)
- Prestige Holiday (5)
- Pass The Property (4)
- Curated Property (2)
- Finest Retreats (2)
- HelloGuest Limited (2)
- Host & Stay (2)
- The Cricketers Inn (2)
- Travelnest Ltd (2)
- ALSENED LTD (1)
- Belvilla by OYO (1)
- Blake (1)
- Hoseasons (1)
- Port Isaac Bay Holidays (1)
- Staybridge Suites (1)
- VanZyl (1)
Operators are indexed when they run at least 26 listings nationally and count Winchester among their markets. See the full interactive Winchester market report for the map, charts, and operator comparison.
How Winchester compares
Winchester ranks 102nd of 598 tracked markets in the United Kingdom, with 0.2% of national supply. Markets of similar size:
-
Lewes 1,057 listings
-
Pwllheli 1,049 listings
-
Salcombe 1,049 listings
-
Shrewsbury 1,045 listings
-
Stratford-Upon-Avon 1,040 listings
-
Eastbourne 1,035 listings
Photo credits
- Lewes: Photo: Harveys Brewery (Lewes) by Wikimedia Commons contributors · Public domain · cropped and resized for display, via Wikimedia Commons
- Pwllheli: Photo: Pwllheli'n dathlu ei Chymreictod - Pwllheli celebrates its Welshness - geograph.org.uk - 498624 by Alan Fryer · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Salcombe: Photo: Salcombechurch by Rodw · 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
- Stratford-Upon-Avon: Photo: Shakespeare's Birthplace, Stratford-upon-Avon - Sept 2012 by Diliff · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons
- Eastbourne: Photo: Eastbourne Beach - geograph.org.uk - 1582936 by Oast House Archive · CC BY-SA 2.0 · 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 1,049 tracked short-term rental listings as of 2026-06-07: 792 on Airbnb and 257 on Booking.com.
Who is the largest short-term rental operator in Winchester?
The largest professional operator in Winchester is Cottages.com, with 43 local listings.
Is Airbnb or Booking.com bigger in Winchester?
Airbnb is bigger in Winchester, with 792 listings against 257 on Booking.com.
How many professional operators run listings in Winchester?
20 professional operators (26+ listings nationally) have a tracked presence 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 1,049 public short-term rental listings in Winchester, matching Airbnb and Booking.com supply to the operators who run it. Operators shown have at least 26 listings on Airbnb or Booking.com nationally. Snapshot dates: Airbnb , Booking.com .
Spotted an inconsistency, or want fresher data for Winchester? Report a data issue or request an update — corrections land with the next data refresh.