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Short-term rentals in Cheltenham

Cheltenham is the 33rd-largest of 597 short-term rental markets across the United Kingdom: 1,720 listings, 69% on Airbnb. 21% of supply is run by professional operators, below the median market's 39%, led by Jason and Philip Serviced Accommodation (90 listings).

Explore the interactive Cheltenham report
View of Cheltenham
Photo: Cheltenham.from.leckhampton.arp by Arpingstone · Public domain · cropped and resized for display, via Wikimedia Commons

Data updated

Tracked listings
1,720
Market rank
#33 / 597
National share
0.3%
Named professional operators
23

Airbnb vs Booking.com in Cheltenham

In Cheltenham, Airbnb leads with 1,184 listings (69%), 2.2× the 536 on Booking.com (31%).

Where the listings are in Cheltenham

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 1,720 tracked listings — open the full interactive report

Market structure in Cheltenham

Booking.com supply is more professionalised than Airbnb's: 37% of Booking.com listings sit with operators of that size, against 13% on Airbnb. The 23 named professional operators run 264 local listings between them, and the three largest — Jason and Philip Serviced Accommodation, Red Kite Stays and Sykes Holiday Cottages — account for 59% of that. The other 90 listings run by operators with 26 or more listings belong to operators without a published profile.

Professional share
21%
Median market
39%
Single-listing hosts
39%

Listings by operator portfolio size

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

  • Single listing 666
  • 2–5 listings 367
  • 6–25 listings 333
  • 26+ (professional) 354

Listings by property type

Houses, cottages & holiday homes make up 41% of Cheltenham's classified listings, followed by Apartments & flats (39%).

  • Houses, cottages & holiday homes 700
  • Apartments & flats 676
  • Private & shared rooms 203
  • B&Bs & guest houses 98
  • Hotels & hostels 27
  • Unique & outdoor 16

Largest operators in Cheltenham

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 Cheltenham, ranked by local tracked listings.
# Operator Listings Airbnb score Booking.com score Portfolio reviews
1 Jason and Philip Serviced Accommodation 90 4.89 / 5 9.3 / 10 3,632
2 Red Kite Stays 45 4.79 / 5 8.8 / 10 6,953
3 Sykes Holiday Cottages 20 4.70 / 5 8.9 / 10 179,990
4 My Property Host 18 4.29 / 5 7.4 / 10 15,689
5 Bolthole Retreats 15 4.82 / 5 9.0 / 10 7,344
6 Pass the Keys 13 4.75 / 5 8.1 / 10 62,567
7 Guesthoo 11 4.82 / 5 8.7 / 10 16,142
8 holidaycottages.co.uk 11 4.73 / 5 8.9 / 10 73,474
9 mystayinn LIMITED 11 4.52 / 5 7.6 / 10 7,060
10 Birch Stays Ltd 4 4.90 / 5 9.2 / 10 1,440

The other 13 professional operators in Cheltenham

Local listings

Browse the full United Kingdom operator directory →

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

How Cheltenham compares

Cheltenham ranks 33rd of 597 tracked markets in the United Kingdom, with 0.3% 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 .

Cheltenham market FAQ

How many short-term rentals are in Cheltenham?

Cheltenham has 1,720 short-term rental listings as of August 2026: 1,184 on Airbnb and 536 on Booking.com.

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

The largest professional operator in Cheltenham is Jason and Philip Serviced Accommodation, with 90 local listings.

How professionalised is the Cheltenham short-term rental market?

21% of Cheltenham's listings (354 of 1,720) 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: 37% of Booking.com listings sit with operators of that size, against 13% on Airbnb. The 23 named professional operators run 264 local listings between them, and the three largest — Jason and Philip Serviced Accommodation, Red Kite Stays and Sykes Holiday Cottages — account for 59% of that. The other 90 listings run by operators with 26 or more listings belong to operators without a published profile.

Is Airbnb or Booking.com bigger in Cheltenham?

In Cheltenham, Airbnb leads with 1,184 listings (69%), 2.2× the 536 on Booking.com (31%).

How many professional operators run listings in Cheltenham?

23 named professional operators run listings in Cheltenham. 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 1,720 public short-term rental listings in Cheltenham, 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 Cheltenham? Report a data issue or request an update — corrections land with the next data refresh.