myDataValue

Short-term rentals in Cheltenham

Cheltenham has 1,720 tracked short-term rental listings in myDataValue's November 2026 snapshot, 1,184 on Airbnb and 536 on Booking.com. That ranks it 33rd of 597 short-term rental markets across the United Kingdom, with 69% of its listings on Airbnb. 22% of supply is run by professional operators, below the median market's 41%, led by Jason and Philip Serviced Accommodation (91 listings). Counts are tracked public listings, not total supply.

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
24

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 15% on Airbnb. The 24 named professional operators run 330 local listings between them, and the three largest — Jason and Philip Serviced Accommodation, Luxury Apartments and Red Kite Stays — account for 57% of that. The other 45 listings run by operators with 26 or more listings belong to operators without a published profile.

Professional share
22%
Median market
41%
Single-listing hosts
37%

Listings by operator portfolio size

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

  • Single listing 644
  • 2–5 listings 368
  • 6–25 listings 333
  • 26+ (professional) 375

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 675
  • Private & shared rooms 204
  • 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 91 4.89 / 5 9.3 / 10 3,667
2 Luxury Apartments 53 4.89 / 5 9.6 / 10 242
3 Red Kite Stays 45 4.79 / 5 8.9 / 10 6,959
4 Sykes Holiday Cottages 20 4.69 / 5 8.9 / 10 184,961
5 Signature Stays 19 4.72 / 5 8.4 / 10 609
6 My Property Host 18 4.28 / 5 7.4 / 10 15,849
7 Bolthole Retreats 15 4.82 / 5 9.0 / 10 7,128
8 Pass the Keys 13 4.75 / 5 8.1 / 10 63,230
9 holidaycottages.co.uk 11 4.73 / 5 8.8 / 10 82,888
10 mystayinn LIMITED 11 4.48 / 5 7.5 / 10 7,309

The other 14 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 November 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 91 local listings.

How professionalised is the Cheltenham short-term rental market?

22% of Cheltenham's listings (375 of 1,720) are run by operators with 26 or more listings, below the median of 597 markets across the United Kingdom (41%). Booking.com supply is more professionalised than Airbnb's: 37% of Booking.com listings sit with operators of that size, against 15% on Airbnb. The 24 named professional operators run 330 local listings between them, and the three largest — Jason and Philip Serviced Accommodation, Luxury Apartments and Red Kite Stays — account for 57% of that. The other 45 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?

24 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.