myDataValue

Short-term rentals in Chesterfield

Chesterfield has 572 tracked short-term rental listings in myDataValue's November 2026 snapshot, 358 on Airbnb and 214 on Booking.com. That ranks it 288th of 597 short-term rental markets across the United Kingdom, with 63% of its listings on Airbnb. 40% of supply is run by professional operators, in line with the median market's 41%, led by Cottages.com (70 listings). Counts are tracked public listings, not total supply.

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View of Chesterfield
Photo: Chesterfield by Jon Bennett · CC BY 2.0 · cropped and resized for display, via Wikimedia Commons

Data updated

Tracked listings
572
Market rank
#288 / 597
National share
under 0.1%
Named professional operators
16

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.

Airbnb Booking.com 250 sampled locations from 572 tracked listings — open the full interactive report

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 33% on Airbnb. The 16 named professional operators run 211 local listings between them, and the three largest — Cottages.com, Sykes Holiday Cottages and holidaycottages.co.uk — account for 74% of that. The other 20 listings run by operators with 26 or more listings belong to operators without a published profile.

Professional share
40%
Median market
41%
Single-listing hosts
32%

Listings by operator portfolio size

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

  • Single listing 182
  • 2–5 listings 136
  • 6–25 listings 23
  • 26+ (professional) 231

Listings by property type

Houses, cottages & holiday homes make up 66% of Chesterfield's classified listings, followed by Apartments & flats (12%).

  • Houses, cottages & holiday homes 376
  • Apartments & flats 69
  • Private & shared rooms 41
  • Unique & outdoor 40
  • B&Bs & guest houses 29
  • Hotels & hostels 17

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.

Largest operators in Chesterfield, ranked by local tracked listings.
# Operator Listings Airbnb score Booking.com score Portfolio reviews
1 Cottages.com 70 4.77 / 5 9.0 / 10 221,687
2 Sykes Holiday Cottages 64 4.69 / 5 8.9 / 10 184,961
3 holidaycottages.co.uk 23 4.73 / 5 8.8 / 10 82,888
4 Smart Corporate Stays Ltd 20 4.04 / 5 6.3 / 10 523
5 Home Crowd Properties 11 4.67 / 5 8.1 / 10 1,730
6 Travelnest Ltd 6 4.52 / 5 8.0 / 10 99,168
7 Devonshire Hotels & Restaurants Group Limited 3 4.81 / 5 9.1 / 10 2,593
8 Finest Retreats 2 4.65 / 5 8.5 / 10 14,946
9 HelloGuest Limited 2 4.71 / 5 8.1 / 10 8,648
10 My Property Host 2 4.28 / 5 7.4 / 10 15,849

The other 6 professional operators in Chesterfield

Local listings

Browse the full United Kingdom operator directory →

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:

Photo credits

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 November 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 70 local listings.

How professionalised is the Chesterfield short-term rental market?

40% of Chesterfield's listings (231 of 572) are run by operators with 26 or more listings, in line with the median of 597 markets across the United Kingdom (41%). Booking.com supply is more professionalised than Airbnb's: 52% of Booking.com listings sit with operators of that size, against 33% on Airbnb. The 16 named professional operators run 211 local listings between them, and the three largest — Cottages.com, Sykes Holiday Cottages and holidaycottages.co.uk — account for 74% of that. The other 20 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?

16 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 .

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