Vacation rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in New Tupton
Studio Annexe on the Edge of the Peak District
A bright and airy ground floor annexe, used solely for guests. With its own entrance, a comfortable double bed, fully equipped kitchen and outdoor patio area, you are guaranteed a relaxing and private stay. Nestled away in the village of Tupton on the edge of the Peak District, we hope that you can find a place to relax, eat and explore. If you're with us for work, moving house or to see family, then we have everything you need from pots and pans to a washing machine as well as a space to park.
28 Apr – 5 May
$120 NZD per night
4.85 out of 5 average rating, 252 reviews
Guest favourite
Cottage in Chesterfield
Chatsworth Cottage
Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.
3–10 Aug
$240 NZD per night
4.92 out of 5 average rating, 214 reviews
Guest favourite
Guest suite in Ashover
Hunger Hill Farm Studio - Derbyshire Dales
Set in the glorious Peak District in a rural location is our lovely self contained studio. Glorious views over rolling countryside and very close to Chatsworth House and Stanedge Golf Club, you are guaranteed a peaceful stay here. With a lovely country pub, the very popular wedding venue of the Peak Edge Hotel within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here.
12–19 Jun
$171 NZD per night
4.97 out of 5 average rating, 268 reviews

Popular amenities for Chesterfield holiday rentals

Stay near Chesterfield's top sights

Morrisons5 locals recommend
Queens Park5 locals recommend
Queen's Park Sports Centre3 locals recommend
Cineworld Cinema Chesterfield19 locals recommend
Chesterfield Market8 locals recommend
The Market Pub4 locals recommend

Other great holiday rentals in Chesterfield

Guest favourite
Apartment in Sheffield/Chesterfield
Peaceful setting, close to amenities and transport
2–9 Aug
$135 NZD per night
4.99 out of 5 average rating, 141 reviews
Guest favourite
Home in Derbyshire
Florries House is on the edge of the Peak District
25 Feb – 4 Mar
$97 NZD per night
4.97 out of 5 average rating, 96 reviews
Guest favourite
Home in Derbyshire
Bright - 2 Bedroomed House in Derbyshire
27 Jan – 3 Feb
$170 NZD per night
4.8 out of 5 average rating, 44 reviews
Guest favourite
Townhouse in Derbyshire
Cottage by the Park Chesterfield - Peak district
2–9 Aug
$202 NZD per night
4.86 out of 5 average rating, 74 reviews
Guest favourite
Home in Derbyshire
Cosy 2 bed home CHESTERFIELD
31 Mar – 7 Apr
$188 NZD per night
4.95 out of 5 average rating, 21 reviews
Superhost
Apartment in Dronfield
The Old Bank Luxury Serviced Apartments, Dronfield
15–22 Nov
$170 NZD per night
4.91 out of 5 average rating, 34 reviews
Guest favourite
Home in Derbyshire
Home from Home with private rose garden
19–26 Sep
$237 NZD per night
4.99 out of 5 average rating, 89 reviews
Guest favourite
Guest suite in Derbyshire
The Loft
15–22 Oct
$186 NZD per night
4.97 out of 5 average rating, 38 reviews
Guest favourite
Barn in Bolsover
Gravediggers Cottage
28 Jun – 5 Jul
$208 NZD per night
4.95 out of 5 average rating, 37 reviews
Guest favourite
Bungalow in Old Whittington
Rosies Retreat
7–14 Feb
$188 NZD per night
4.87 out of 5 average rating, 31 reviews
Guest favourite
Cottage in Holymoorside
Tranquil cosy cottage close to the Peak District
21–28 Oct
$215 NZD per night
4.92 out of 5 average rating, 60 reviews
Guest favourite
Guest suite in Holmesfield
One Bedroom Studio with full kitchen & log burner.
9–16 Dec
$206 NZD per night
4.96 out of 5 average rating, 46 reviews

Quick stats about holiday rentals in Chesterfield

Total rentals

100 properties

Rentals with dedicated workspaces

50 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

5.4K reviews

Nightly prices starting at

$33 NZD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield