A stone path winding through a valley with a sunset in the background.

Holiday Homes in Chesterfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chesterfield holiday homes

A modern living room with leather sofas, a round coffee table, and a flat-screen TV.

1. Peak Avenue Retreat - Dog Friendly with Garden!

Peak Avenue Retreat - Dog Friendly with Garden!
Derbyshire
The price is AU$614
includes taxes & fees
30 Oct - 31 Oct
Peak Avenue Retreat - Dog Friendly with Garden!
Dining

2. 3-bed House - Sleeps 6 - Free Parking - Garden

3-bed House - Sleeps 6 - Free Parking - Garden
3.0 star property
Sheffield
The price is AU$395
includes taxes & fees
18 Nov - 19 Nov
3-bed House - Sleeps 6 - Free Parking - Garden
A stone house with a wooden bench in front, a car parked nearby, and a stone wall in the background.

3. Robin Hood Tower

Robin Hood Tower
3.0 star property
Matlock
10.0 out of 10, Exceptional, (15 reviews)
"This is a wonderfully quirky and unique place to stay. The accommodation is just perfect. Hosts Steve and Elaine have created a tranquil and idyllic tiny retreat at Robin Hood Tower. Comms were great and Steve showed us around, sharing local history and top tips for our trip. Canal side walks were glorious. A magical stay."
United Kingdom
Heidi
The price is AU$403
includes taxes & fees
19 Oct - 20 Oct
Robin Hood Tower
A living room with a large sectional sofa, a television, a fireplace, and a mirror.

4. Charress House, 6/7 Bedrooms, 10 beds, 3 bathrooms Contractors/Friends/Families.

Charress House, 6/7 Bedrooms, 10 beds, 3 bathrooms Contractors/Friends/Families.
Whitwell
The price is AU$262
includes taxes & fees
9 Nov - 10 Nov
Charress House, 6/7 Bedrooms, 10 beds, 3 bathrooms Contractors/Friends/Families.
A neatly made bed with a plaid blanket, a decorative pillow, and a rolled towel on the bed.

5. 3 Bed House Sleeps 5 - Free Parking - Tv & WiFi

3 Bed House Sleeps 5 - Free Parking - Tv & WiFi
Sheffield
The price is AU$214
includes taxes & fees
19 Oct - 20 Oct
3 Bed House Sleeps 5 - Free Parking - Tv & WiFi
A bedroom with a bed, a desk, a chair, and a TV on the wall.

6. Spacious & Serene Ensuite Room with Bay Window | Peaceful Sheffield Retreat

Spacious & Serene Ensuite Room with Bay Window | Peaceful Sheffield Retreat
Hillsborough
10.0 out of 10, Exceptional, (1 review)
"Perfect room great are nice and clean and very quiet"
United States
wendy swaine
The price is AU$158
includes taxes & fees
3 Nov - 4 Nov
Spacious & Serene Ensuite Room with Bay Window | Peaceful Sheffield Retreat
A stone building with a sign reading "Kingfisher Lodge."

7. Stone built self-catering lodge in stunning location

Stone built self-catering lodge in stunning location
Froggatt
10.0 out of 10, Exceptional, (13 reviews)
"Amazing location enjoyed every minute we stayed here Katie and Rod were very friendly beautiful little cottage"
United Kingdom
Michelle C.
The price is AU$216
includes taxes & fees
20 Oct - 21 Oct
Stone built self-catering lodge in stunning location
A corner house with a bay window, a white door, and a brick wall.

8. Cozy Double Bedroom with Private Bathroom

Cozy Double Bedroom with Private Bathroom
Hillsborough
The price is AU$91
includes taxes & fees
3 Nov - 4 Nov
Cozy Double Bedroom with Private Bathroom
Restaurant

9. Old Nags Head

Old Nags Head
3.0 star property
Hope Valley
10.0 out of 10, Exceptional, (3 reviews)
"Perfect location. Warm staff. Great room."
United Kingdom
Kai
The price is AU$272
includes taxes & fees
19 Oct - 20 Oct
Old Nags Head
A modern bedroom with two beds, a window with blinds, a radiator, and a dark door.

10. Cheerful and Cosy 4 bedroom House

Cheerful and Cosy 4 bedroom House
Upperthorpe
10.0 out of 10, Exceptional, (2 reviews)
"Really comfortable, really helpful communicative host and we would definitely stay again"
United Kingdom
Joanna B.
The price is AU$405
includes taxes & fees
19 Oct - 20 Oct
Cheerful and Cosy 4 bedroom House
A compact kitchen with a sink, stove, microwave, and oven.

11. Clean Spacious Walkley Home, 8pp, Free Street Parking

Clean Spacious Walkley Home, 8pp, Free Street Parking
South Yorkshire
The price is AU$331
includes taxes & fees
19 Oct - 20 Oct
Clean Spacious Walkley Home, 8pp, Free Street Parking
A bedroom with a bed, a chair, a desk, a TV, and a mirror.

12. Stylish Private Guest Suite | Sleeps 5 | Free Parking |Near City & Peak District

Stylish Private Guest Suite | Sleeps 5 | Free Parking |Near City & Peak District
Hillsborough
10.0 out of 10, Exceptional, (1 review)
"Nice property, lots of sleeping space, outside space good too. No cooker or oven, so don't plan to cook whilst staying. Lots of nice restaurants and take aways."
United States
Reena P.
The price is AU$263
includes taxes & fees
20 Oct - 21 Oct
Stylish Private Guest Suite | Sleeps 5 | Free Parking |Near City & Peak District
A modern living room with a sofa, coffee table, and a TV. There is a kitchen in the background with a stove, oven, and cabinets.

13. 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 AU$305
includes taxes & fees
25 Oct - 26 Oct
No 4
A hotel room with a large bed, a mirror, two windows with curtains, and a chandelier.

14. 2-bed Hillside House - Sleeps 4, Garden & Parking

2-bed Hillside House - Sleeps 4, Garden & Parking
4.0 star property
Heeley
2.0 out of 10, (1 review)
"The description does not state anywhere that this property is a a house share. It specially states when booking, that you and your guests will have entirety of the property to yourselves. Upon arrival, the host was at the property and told myself that he would be staying in the room above. There were no safety precautions in place to separate ourselves from the host. The host then offered us a refund, but when contacted by Expedia declined this. Appalling customer service."
United Kingdom
Isabelle
The price is AU$228
includes taxes & fees
1 Nov - 2 Nov
2-bed Hillside House - Sleeps 4, Garden & Parking
A hotel room with a large bed, a mirror, two windows with curtains, and a chandelier.

15. Charming & Stylish Home-Heeley, Heart of Sheffield

Charming & Stylish Home-Heeley, Heart of Sheffield
Heeley
The price is AU$322
includes taxes & fees
1 Nov - 2 Nov
Charming & Stylish Home-Heeley, Heart of Sheffield
A modern kitchen with a dining area, featuring a herringbone wood floor, a central island with chairs, and a window with blinds.

16. Stylish house in Rotherham/Sheffield area, with free private parking.

Stylish house in Rotherham/Sheffield area, with free private parking.
Rotherham
The price is AU$329
includes taxes & fees
22 Oct - 23 Oct
Stylish house in Rotherham/Sheffield area, with free private parking.
A bedroom with a bed, a desk with a chair, a hanging light fixture, and a small plant.

17. Spacious 5BR Sheffield Home | City Access & WiFi

Spacious 5BR Sheffield Home | City Access & WiFi
Sheffield
The price is AU$944
includes taxes & fees
9 Nov - 10 Nov
Spacious 5BR Sheffield Home | City Access & WiFi
A hotel room with a bed, a nightstand, a lamp, a mirror, and a door.

18. 3-bed House - Sleeps 6 - Free Parking - Garden

3-bed House - Sleeps 6 - Free Parking - Garden
Sheffield
The price is AU$391
includes taxes & fees
19 Oct - 20 Oct
3-bed House - Sleeps 6 - Free Parking - Garden
A modern living room with a flat-screen TV mounted on the wall, a sofa, a coffee table, and a fireplace. There are two chairs and a window with curtains.

19. Stylish Spacious 3-Bed Sheffield Home

Stylish Spacious 3-Bed Sheffield Home
Highfield
The price is AU$480
includes taxes & fees
12 Nov - 13 Nov
Stylish Spacious 3-Bed Sheffield Home
A modern living room with a sofa, a coffee table, a fireplace, and a flat-screen TV mounted on the wall.

20. URBA Luxury Stays 3 Bed Home Sheffield Central

URBA Luxury Stays 3 Bed Home Sheffield Central
Norfolk Park
The price is AU$515
includes taxes & fees
1 Nov - 2 Nov
URBA Luxury Stays 3 Bed Home Sheffield Central
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Four Points Flex by Sheraton Nottingham

Four Points Flex by Sheraton Nottingham

10/10 Excellent
"Lovely cosy room bright and very clean staff very pleasant and helpful in all a fabulous hotel very happy"
Richard 1-night trip
Posted 3 hours ago
Four Points Flex by Sheraton Nottingham

Find out more about Chesterfield

Chesterfield Holiday Homes information

Number of reviews
39
Accommodation
1072 Holiday Homes
Lowest Price
AU$91
Highest Price
AU$515

Explore a world of travel with Expedia