A historic building with black and white timber framing, a prominent clock tower, and a pointed spire in the background.

Chesterfield Private Home Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Chesterfield holiday homes

Exterior

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
3.0 star property
Chesterfield
The price is S$287
includes taxes & fees
22 Jul - 23 Jul
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Private kitchen

Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is S$199
includes taxes & fees
2 Aug - 3 Aug
Commuters Getaway Chesterfield
Terrace/patio

2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"Property is self catering house at edge of the town. Spacious and decent kitchen. Road quiet (liked that) and easy access to nature reserve/countryside walks. Parking a bit of an issue but didn’t detract from our stay. "
United Kingdom
Philip
The price is S$186
includes taxes & fees
22 Jul - 23 Jul
2bed - Garden-pets-freeparking-m1connections
Fridge, microwave, oven, stovetop

a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is S$219
includes taxes & fees
26 Jul - 27 Jul
a Quiet Semi Rural Property Located in Bolsover
Balcony

Christmas Cottage

Christmas Cottage
3.5 star property
Alfreton
The price is S$929
includes taxes & fees
31 Jul - 1 Aug
Christmas Cottage
Exterior

Robin Hood Tower

Robin Hood Tower
3.0 star property
Matlock
10.0 out of 10, Exceptional, (13 reviews)
"Lovely location with everything we needed for a very peaceful vacation. The hosts were very welcoming and gave us a little tour of the grounds and lots of information about the area."
United Kingdom
Judith
The price is S$365
includes taxes & fees
21 Jul - 22 Jul
Robin Hood Tower
Exterior

Hayeswood Lodge Luxury Accommodation

Hayeswood Lodge Luxury Accommodation
3.5 star property
Ilkeston
10.0 out of 10, Exceptional, (35 reviews)
"Great place - very clean and a lovely little breakfast"
United Kingdom
Ian
The price is S$262
includes taxes & fees
21 Jul - 22 Jul
Hayeswood Lodge Luxury Accommodation
3 bedrooms, free WiFi, bed sheets

3 Bed House Sleeps 5 - Free Parking - Tv & Wifi

3 Bed House Sleeps 5 - Free Parking - Tv & Wifi
3.0 star property
Sheffield
6.0 out of 10, (1 review)
"Overall if you are a dirtbag climber and just in sheffield for a quick trip this place totally gets the job done. Our biggest issues were that there was no shower curtain so the bathroom flooded when anyone showered, none of the bathrooms had soap, and overall just super limited amenities. Also the trash out front was absolutely overflowing and was all over the yard. Honestly would stay again in a pinch, just would come with lower expectations."
United Kingdom
Elizabeth
The price is S$239
includes taxes & fees
26 Jul - 27 Jul
3 Bed House Sleeps 5 - Free Parking - Tv & Wifi
Restaurant

Old Nags Head

Old Nags Head
3.0 star property
Hope Valley
The price is S$185
includes taxes & fees
21 Jul - 22 Jul
Old Nags Head
Private kitchen

Cozy 2 Bedroom Home in Hucknall, Perfect for a Relaxing Getaway

Cozy 2 Bedroom Home in Hucknall, Perfect for a Relaxing Getaway
2.0 star property
Nottingham
The price is S$203
includes taxes & fees
31 Jul - 1 Aug
Cozy 2 Bedroom Home in Hucknall, Perfect for a Relaxing Getaway
Interior

Hope Cottage

Hope Cottage
3.5 star property
Hope Valley
The price is S$1,157
includes taxes & fees
26 Jul - 27 Jul
Hope Cottage
Egyptian cotton sheets, premium bedding, iron/ironing board, travel cot

Studio Self contained flat free Parking

Studio Self contained flat free Parking
2.0 star property
Nottingham
8.6 out of 10, Excellent, (16 reviews)
"Clean, comfortable, good location, clear instructions "
United Kingdom
Andrew
The price is S$86
includes taxes & fees
2 Aug - 3 Aug
Studio Self contained flat free Parking
Lounge

No 4

No 4
3.5 star property
Mansfield
6.0 out of 10, (3 reviews)
"Just what we required for our family of 4 for a last minute accommodation with well equipped kitchen, comfortable beds and washing machine. Easy secure parking, friendly neighbours and lovely park at the end of the street."
Australia
Graham
The price is S$311
includes taxes & fees
24 Jul - 25 Jul
No 4
2 bedrooms, free WiFi, bed sheets

Sheffield Hillside Retreat

Sheffield Hillside Retreat
4.0 star property
Heeley
The price is S$241
includes taxes & fees
22 Jul - 23 Jul
Sheffield Hillside Retreat
Garden

use With Modern Comforts

use With Modern Comforts
2.0 star property
Basford
The price is S$335
includes taxes & fees
25 Jul - 26 Jul
use With Modern Comforts
Dining

2 Bed House - Sleeps 4 - Pets - Garden - Parking

2 Bed House - Sleeps 4 - Pets - Garden - Parking
3.0 star property
Newark
10.0 out of 10, Exceptional, (8 reviews)
"Lovely house, super clean and comfortable. Kitchen really well equipped, everything needed for a stay, milk and orange juice in the fridge on arrival. Perfect for our dog, Freddie, too. Wish we could have stayed longer! "
United Kingdom
Kate
The price is S$202
includes taxes & fees
3 Aug - 4 Aug
2 Bed House - Sleeps 4 - Pets - Garden - Parking
Interior

Lacewood

Lacewood
3.0 star property
Buxton
The price is S$712
includes taxes & fees
24 Jul - 25 Jul
Lacewood
4 bedrooms, iron/ironing board, free WiFi, bed sheets

4br-sleeps8-privategarden-freeparking

4br-sleeps8-privategarden-freeparking
3.5 star property
Nottingham
9.4 out of 10, Exceptional, (3 reviews)
"My family had a fantastic stay at the house in Nottingham! The property was clean, cozy, and thoughtfully furnished—everything felt welcoming and well-maintained. The location was ideal, with easy access to entertainment, food, and the city center. The host was wonderful. It was the perfect base for exploring Nottingham, and I truly appreciated the quiet comfort of the space after busy days out. I would absolutely stay here again and highly recommend it to anyone visiting the area!"
United States
Frederic
The price is S$366
includes taxes & fees
2 Aug - 3 Aug
4br-sleeps8-privategarden-freeparking
Dining

Green Corner House Sleeps 6 & Free Parking

Green Corner House Sleeps 6 & Free Parking
3.0 star property
Nottingham
The price is S$290
includes taxes & fees
31 Jul - 1 Aug
Green Corner House Sleeps 6 & Free Parking
Dining

2 Bed Home - Parking for 2, Wifi & Garden

2 Bed Home - Parking for 2, Wifi & Garden
3.0 star property
Nottingham
The price is S$187
includes taxes & fees
9 Aug - 10 Aug
2 Bed Home - Parking for 2, Wifi & Garden
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterfield Hotel Reviews

Hex Wildlife Hotel

Hex Wildlife Hotel

10/10 Excellent
"A modern fresh and clean hotel. Very quiet, really comfy beds, large television and a great assortment of tea and coffee options in the room Including tea bags, coffee bags, fruit tea and hot chocolate and biscuits. My one improvement would be to have the same extensive range of drinks at breakfast instead of just normal tea and various coffee options "
Peter 1-night trip
Posted 5 hours ago
Hex Wildlife Hotel

Find out more about Chesterfield

Chesterfield Private Holiday Homes information

Number of reviews
72
Accommodation
288 Private Holiday Homes
Lowest Price
S$86
Highest Price
S$1,157