Short-term rentals in Chesterfield
Chesterfield is the 288th-largest of 597 short-term rental markets across the United Kingdom: 572 listings, 63% on Airbnb. 37% of supply is run by professional operators, in line with the median market's 39%, led by Cottages.com (68 listings).
Data updated
- Tracked listings
- 572
- Market rank
- #288 / 597
- National share
- under 0.1%
- Named professional operators
- 13
Airbnb vs Booking.com in Chesterfield
In Chesterfield, Airbnb leads with 358 listings (63%), versus 214 on Booking.com (37%).
Where the listings are in Chesterfield
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 Chesterfield
Booking.com supply is more professionalised than Airbnb's: 52% of Booking.com listings sit with operators of that size, against 28% on Airbnb. The 13 named professional operators run 174 local listings between them, and the three largest — Cottages.com, Sykes Holiday Cottages and holidaycottages.co.uk — account for 89% of that. The other 40 listings run by operators with 26 or more listings belong to operators without a published profile.
- Professional share
- 37%
- Median market
- 39%
- Single-listing hosts
- 33%
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 66% of Chesterfield's classified listings, followed by Apartments & flats (12%).
Largest operators in Chesterfield
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 | 68 | 4.77 / 5 | 9.0 / 10 | 217,587 |
| 2 | Sykes Holiday Cottages | 64 | 4.70 / 5 | 8.9 / 10 | 179,990 |
| 3 | holidaycottages.co.uk | 23 | 4.73 / 5 | 8.9 / 10 | 73,474 |
| 4 | Travelnest Ltd | 6 | 4.56 / 5 | 8.0 / 10 | 95,073 |
| 5 | Finest Retreats | 2 | 4.64 / 5 | 8.5 / 10 | 13,960 |
| 6 | HelloGuest Limited | 2 | 4.71 / 5 | 8.1 / 10 | 7,597 |
| 7 | Hoseasons | 2 | 4.66 / 5 | 8.6 / 10 | 11,713 |
| 8 | My Property Host | 2 | 4.29 / 5 | 7.4 / 10 | 15,689 |
| 9 | Best Western The Dartmouth Golf, Hotel and Spa | 1 | 4.73 / 5 | 7.9 / 10 | 285,489 |
| 10 | Host & Stay | 1 | 4.57 / 5 | 8.3 / 10 | 59,134 |
The other 3 professional operators in Chesterfield
Local listings
- Houst 1 listing
- Staybridge Suites 1 listing
- The Cricketers Inn 1 listing
Operators enter the index after reaching 26 listings across the United Kingdom and count Chesterfield among their markets. See the full interactive Chesterfield market report for additional filters and operator comparisons.
How Chesterfield compares
Chesterfield ranks 288th of 597 tracked markets in the United Kingdom, with under 0.1% of tracked supply in this coverage. Markets of similar size:
-
Trearddur 580 listings
- Fife 578 listings
-
Bicester 572 listings
-
Lancaster 571 listings
-
Stoney Middleton 571 listings
-
Burford 570 listings
Photo credits
- Trearddur: Photo: A good site for a windmill (geograph 3482177) by Ian Greig · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Bicester: Photo: Greengrocer in Sheep Street, Bicester 1 - geograph.org.uk - 989713 by Jonathan Billinger · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Lancaster: Photo: City of Lancaster (2) by David P · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Stoney Middleton: Photo: MiddletonDale by Dave.Dunford · Public domain · cropped and resized for display, via Wikimedia Commons
- Burford: Photo: Main Street in BurfordOxfordshire, UK by Ettlz at English Wikipedia · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons
.jpg){kind=link}
.jpg){kind=link}
Browse the full United Kingdom city directory or the United Kingdom market report .
Chesterfield market FAQ
How many short-term rentals are in Chesterfield?
Chesterfield has 572 short-term rental listings as of August 2026: 358 on Airbnb and 214 on Booking.com.
Who is the largest short-term rental operator in Chesterfield?
The largest professional operator in Chesterfield is Cottages.com, with 68 local listings.
How professionalised is the Chesterfield short-term rental market?
37% of Chesterfield's listings (214 of 572) are run by operators with 26 or more listings, in line with the median of 597 markets across the United Kingdom (39%). Booking.com supply is more professionalised than Airbnb's: 52% of Booking.com listings sit with operators of that size, against 28% on Airbnb. The 13 named professional operators run 174 local listings between them, and the three largest — Cottages.com, Sykes Holiday Cottages and holidaycottages.co.uk — account for 89% of that. The other 40 listings run by operators with 26 or more listings belong to operators without a published profile.
Is Airbnb or Booking.com bigger in Chesterfield?
In Chesterfield, Airbnb leads with 358 listings (63%), versus 214 on Booking.com (37%).
How many professional operators run listings in Chesterfield?
13 named professional operators run listings in Chesterfield. 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 572 public short-term rental listings in Chesterfield, 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 Chesterfield? Report a data issue or request an update — corrections land with the next data refresh.