Short-term rentals in Chesterfield
Local supply is split fairly evenly between the two platforms. Its largest professional operator, Cottages.com, runs 67 listings locally.
Data updated
- Tracked listings
- 548
- Market rank
- #334 / 598
- National share
- under 0.1%
- Professional operators
- 14
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 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.
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 | Cottages.com | 67 | 4.77 / 5 | 9.0 / 10 | 213,860 |
| 2 | Sykes Holiday Cottages | 67 | 4.69 / 5 | 8.9 / 10 | 163,699 |
| 3 | holidaycottages.co.uk | 21 | 4.73 / 5 | 8.9 / 10 | 75,737 |
| 4 | Travelnest Ltd | 6 | 4.53 / 5 | 8.1 / 10 | 83,730 |
| 5 | Finest Retreats | 2 | 4.64 / 5 | 8.6 / 10 | 13,170 |
| 6 | HelloGuest Limited | 2 | 4.71 / 5 | 8.1 / 10 | 7,329 |
| 7 | Hoseasons | 2 | 4.66 / 5 | 8.7 / 10 | 11,097 |
| 8 | Pillow Property Partners | 2 | 4.41 / 5 | 8.0 / 10 | 4,484 |
| 9 | Best Western The Dartmouth Golf, Hotel and Spa | 1 | 4.72 / 5 | 8.0 / 10 | 293,608 |
| 10 | Host & Stay | 1 | 4.57 / 5 | 8.3 / 10 | 57,680 |
All 14 professional operators in Chesterfield
Local listings
- Cottages.com 67 listings
- Sykes Holiday Cottages 67 listings
- holidaycottages.co.uk 21 listings
- Travelnest Ltd 6 listings
- Finest Retreats 2 listings
- HelloGuest Limited 2 listings
- Hoseasons 2 listings
- Pillow Property Partners 2 listings
- Best Western The Dartmouth Golf, Hotel and Spa 1 listing
- Host & Stay 1 listing
- Luxury Cottages 1 listing
- My Property Host 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. Published profile URLs remain stable across data refreshes. See the full interactive Chesterfield market report for additional filters and operator comparisons.
How Chesterfield compares
Chesterfield ranks 334th of 598 tracked markets in the United Kingdom, with under 0.1% of tracked supply in this coverage. Markets of similar size:
-
Charlestown 552 listings
-
Rhyl 552 listings
-
Llandysul 550 listings
-
Oakham 548 listings
-
Rhosneigr 548 listings
- Fife 547 listings
Photo credits
- Charlestown: Photo: A Charlestown scene - geograph.org.uk - 1184479 by james denham · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Rhyl: Photo: Rhyl Seafront - geograph.org.uk - 388762 by Ian Lee · CC BY-SA 2.0 · cropped and resized for display, via Wikimedia Commons
- Llandysul: Photo: Llandysul by Breckenheimer · Public domain · 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
- 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 Cottages.com, 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?
14 indexed professional operators 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 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.