Short-term rentals in Chesterfield
Local supply is split fairly evenly between the two platforms. Its largest professional operator, Sykes Holiday Cottages, runs 67 listings locally.
Explore the interactive Chesterfield report
Data updated
- Tracked listings
- 548
- Market rank
- #336 / 598
- National share
- under 0.1%
- Professional operators
- 15
Listing mix by platform in Chesterfield
Where the listings are in Chesterfield
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 Chesterfield short-term rental supply looks like
Listings by property type
How Chesterfield'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 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 | Sykes Holiday Cottages | 67 | 4.67 / 5 | 8.9 / 10 | 131,996 |
| 2 | Cottages.com | 64 | 4.76 / 5 | 9.0 / 10 | 184,368 |
| 3 | Holidaycottages.Co.Uk | 20 | 4.73 / 5 | 8.9 / 10 | 35,230 |
| 4 | Travelnest Ltd | 4 | 4.38 / 5 | 8.1 / 10 | 47,351 |
| 5 | Finest Retreats | 2 | 4.60 / 5 | 8.6 / 10 | 9,583 |
| 6 | Pillow Property Partners | 2 | 4.38 / 5 | 8.0 / 10 | 4,511 |
| 7 | Best Western The Dartmouth Golf, Hotel and Spa | 1 | — | 8.0 / 10 | 295,893 |
| 8 | HelloGuest Limited | 1 | — | 8.1 / 10 | 2,817 |
| 9 | Hoseasons | 1 | — | 8.7 / 10 | 8,945 |
| 10 | Host & Stay | 1 | 4.56 / 5 | 8.3 / 10 | 56,399 |
All 15 professional operators in Chesterfield
- Sykes Holiday Cottages (67)
- Cottages.com (64)
- Holidaycottages.Co.Uk (20)
- Travelnest Ltd (4)
- Finest Retreats (2)
- Pillow Property Partners (2)
- Best Western The Dartmouth Golf, Hotel and Spa (1)
- HelloGuest Limited (1)
- Hoseasons (1)
- Host & Stay (1)
- LuxuryCottages.Com (1)
- My Property Host (1)
- Original Cottages Kent & Sussex (1)
- Staybridge Suites (1)
- The Cricketers Inn (1)
Operators are indexed when they run at least 26 listings nationally and count Chesterfield among their markets. See the full interactive Chesterfield market report for the map, charts, and operator comparison.
How Chesterfield compares
Chesterfield ranks 336th of 598 tracked markets in the United Kingdom, with under 0.1% of national supply. Markets of similar size:
-
Rhyl 552 listings
-
Burford 551 listings
-
Oakham 549 listings
- Fife 548 listings
-
Newton Stewart 548 listings
-
Rhosneigr 548 listings
Photo credits
- Rhyl: Photo: Rhyl Seafront - geograph.org.uk - 388762 by Ian Lee · CC BY-SA 2.0 · 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
- Oakham: Photo: Oakham Castle and church spire by Simon Garbutt. SiGarb 21:25, 12 November 2006 (UTC) · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons
- Newton Stewart: Photo: Cree Bridge by Wikimedia Commons contributors · Public domain · cropped and resized for display, via Wikimedia Commons
- Rhosneigr: Photo: Rhosneigr by Porius1 · CC BY-SA 3.0 · cropped and resized for display, via Wikimedia Commons
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 548 tracked short-term rental listings as of 2026-06-07: 359 on Airbnb and 189 on Booking.com.
Who is the largest short-term rental operator in Chesterfield?
The largest professional operator in Chesterfield is Sykes Holiday Cottages, with 67 local listings.
Is Airbnb or Booking.com bigger in Chesterfield?
Supply is fairly balanced: 359 Airbnb and 189 Booking.com listings.
How many professional operators run listings in Chesterfield?
15 professional operators (26+ listings nationally) have a tracked presence 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 548 public short-term rental listings in Chesterfield, 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 Chesterfield? Report a data issue or request an update — corrections land with the next data refresh.