The tow path on the Chesterfield canal on a bright sunny day

Chesterfield Vacation Rentals

  • 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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chesterfield vacation homes

House | Private kitchen

1. Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is CA $138
CA $210 total
includes taxes & fees
Sep 6 - Sep 7
Commuters Getaway Chesterfield
Fridge, microwave, oven, stovetop

2. a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
The price is CA $189
CA $236 total
includes taxes & fees
Aug 22 - Aug 23
a quiet semi rural property located in bolsover
Terrace/patio

3. 2bed - garden-pets-freeparking-M1connections

2bed - garden-pets-freeparking-M1connections
Chesterfield
7.4 out of 10, Good, (3 reviews)
"It was in a good location plenty of amenities close by "
United Kingdom
Ray W.
The price is CA $190
CA $227 total
includes taxes & fees
Sep 1 - Sep 2
2bed - garden-pets-freeparking-M1connections
Terrace/patio

4. 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 CA $140
CA $213 total
includes taxes & fees
Sep 1 - Sep 2
2bed - Garden-pets-freeparking-m1connections
Fridge, microwave, oven, stovetop

5. a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is CA $190
CA $237 total
includes taxes & fees
Aug 18 - Aug 19
a Quiet Semi Rural Property Located in Bolsover
Smart TV

6. Modern Stylish 1 Bedroom Home

Modern Stylish 1 Bedroom Home
Upperthorpe
The price is CA $113
CA $190 total
includes taxes & fees
Aug 18 - Aug 19
Modern Stylish 1 Bedroom Home
Restaurant

7. Old Nags Head

Old Nags Head
3.0 star property
Hope Valley
The price is CA $164
CA $200 total
includes taxes & fees
Aug 19 - Aug 20
Old Nags Head
Exterior detail

8. Stone built self-catering lodge in stunning location

Stone built self-catering lodge in stunning location
Froggatt
10.0 out of 10, Exceptional, (11 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 CA $189
CA $219 total
includes taxes & fees
Aug 20 - Aug 21
Stone built self-catering lodge in stunning location
3 bedrooms, WiFi (free), bed sheets

9. 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 CA $225
CA $270 total
includes taxes & fees
Sep 6 - Sep 7
3 Bed House Sleeps 5 - Free Parking - Tv & Wifi
TV

10. 2 bedroom lux house in Sheffield

2 bedroom lux house in Sheffield
Woodseats
The price is CA $252
CA $355 total
includes taxes & fees
Aug 18 - Aug 19
2 bedroom lux house in Sheffield
Exterior

11. 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 CA $329
CA $394 total
includes taxes & fees
Sep 16 - Sep 17
Robin Hood Tower
Living area

12. Stylish City Stay - Ingram Road Sheffield

Stylish City Stay - Ingram Road Sheffield
Sheffield
The price is CA $271
CA $304 total
includes taxes & fees
Aug 31 - Sep 1
Stylish City Stay - Ingram Road Sheffield
Dining

13. Stylish 3BR House | Perfect for Contrators & Extended Stays

Stylish 3BR House | Perfect for Contrators & Extended Stays
Sheffield
The price is CA $203
CA $431 total
includes taxes & fees
Aug 20 - Aug 21
Stylish 3BR House | Perfect for Contrators & Extended Stays
Interior

14. Boutique 1-Bed Apartment with Skylights – Kelham

Boutique 1-Bed Apartment with Skylights – Kelham
Kelham Island
The price is CA $106
CA $163 total
includes taxes & fees
Aug 18 - Aug 19
Boutique 1-Bed Apartment with Skylights – Kelham
Exterior

15. Cozy Double Bedroom with Private Bathroom

Cozy Double Bedroom with Private Bathroom
Hillsborough
The price is CA $64
CA $94 total
includes taxes & fees
Sep 16 - Sep 17
Cozy Double Bedroom with Private Bathroom
Exterior

16. 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 CA $251
CA $301 total
includes taxes & fees
Aug 18 - Aug 19
Hayeswood Lodge Luxury Accommodation
2 bedrooms, iron/ironing board, WiFi, bed sheets

17. Perfectly located Stunning Retreat in Matlock Bath

Perfectly located Stunning Retreat in Matlock Bath
Matlock
The price is CA $233
CA $233 total
includes taxes & fees
Sep 6 - Sep 7
Perfectly located Stunning Retreat in Matlock Bath
Exterior

18. Private Ensuite Room at Serene Homes Sheffield

Private Ensuite Room at Serene Homes Sheffield
Hillsborough
10.0 out of 10, Exceptional, (2 reviews)
"Host was very welcoming and when i had questions about the rental and future rentals he was timely on his responses. Room was very clean and welcoming and had all the amenities you need."
United States
Chris A.
The price is CA $73
CA $150 total
includes taxes & fees
Sep 7 - Sep 8
Private Ensuite Room at Serene Homes Sheffield
2 bedrooms, WiFi (free), bed sheets

19. Sheffield Hillside Retreat

Sheffield Hillside Retreat
4.0 star property
Heeley
The price is CA $209
CA $251 total
includes taxes & fees
Aug 19 - Aug 20
Sheffield Hillside Retreat
2 bedrooms, WiFi

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

Charming & Stylish Home-Heeley, Heart of Sheffield
Heeley
The price is CA $261
CA $317 total
includes taxes & fees
Sep 3 - Sep 4
Charming & Stylish Home-Heeley, Heart of Sheffield
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

Leonardo Hotel Nottingham

Leonardo Hotel Nottingham

10/10 Excellent
"Very clean and perfect place to stay"
Douglas 1-night trip
Posted 1 hour ago
Leonardo Hotel Nottingham

Find out more about Chesterfield

Chesterfield Vacation Homes information

Number of reviews
69
Accommodation
1178 Vacation Homes
Lowest Price
CA $96
Highest Price
CA $1,004