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Short-term rentals in Windsor

Local supply is split fairly evenly between the two platforms. Its largest professional operator, Tempstay Ltd, runs 160 listings locally.

Explore the interactive Windsor report

Data updated

Tracked listings
1,094
Market rank
#89 / 598
National share
0.2%
Professional operators
16

Listing mix by platform in Windsor

Where the listings are in Windsor

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 1,094 tracked listings — open the full interactive report

What the Windsor short-term rental supply looks like

Listings by property type

How Windsor's tracked listings split across property types on each platform.

  • Houses, cottages & holiday homes 454
  • Apartments & flats 449
  • Private & shared rooms 98
  • B&Bs & guest houses 40
  • Hotels & hostels 40
  • Unique & outdoor 13

Listings by operator portfolio size

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

  • Single listing 343
  • 2–5 listings 237
  • 6–25 listings 190
  • 26+ (professional) 324

Largest operators in Windsor

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 Windsor, ranked by local tracked listings.
# Operator Listings Airbnb score Booking.com score Portfolio reviews
1 Tempstay Ltd 160 4.67 / 5 8.3 / 10 4,155
2 Pass the Keys 21 4.75 / 5 8.1 / 10 59,990
3 Travelnest Ltd 16 4.53 / 5 8.1 / 10 83,730
4 Guest Ready 15 4.58 / 5 8.2 / 10 15,447
5 Smarter Rent 10 4.70 / 5 8.4 / 10 1,676
6 Sykes Holiday Cottages 5 4.69 / 5 8.9 / 10 163,699
7 HelloGuest Limited 4 4.71 / 5 8.1 / 10 7,329
8 Host & Stay 3 4.57 / 5 8.3 / 10 57,680
9 Brookland Stays 2 4.33 / 5 6.8 / 10 296
10 holidaycottages.co.uk 2 4.73 / 5 8.9 / 10 75,737

All 16 professional operators in Windsor

Local listings

Browse the full United Kingdom operator directory →

Operators enter the index after reaching 26 listings across the United Kingdom and count Windsor among their markets. Published profile URLs remain stable across data refreshes. See the full interactive Windsor market report for additional filters and operator comparisons.

How Windsor compares

Windsor ranks 89th of 598 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 .

Windsor market FAQ

How many short-term rentals are in Windsor?

Windsor has 1,094 tracked short-term rental listings as of 2026-06-07: 704 on Airbnb and 390 on Booking.com.

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

The largest professional operator in Windsor is Tempstay Ltd, with 160 local listings.

Is Airbnb or Booking.com bigger in Windsor?

Supply is fairly balanced: 704 Airbnb and 390 Booking.com listings.

How many professional operators run listings in Windsor?

16 indexed professional operators have a tracked presence in Windsor. 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 1,094 public short-term rental listings in Windsor, 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 .

Spotted an inconsistency, or want fresher data for Windsor? Report a data issue or request an update — corrections land with the next data refresh.