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917 Holiday homes

14

Holiday home rental

Chesterfield / Hardstoft

9 20 3 nights min

  • 9 bedrooms
  • Sleeps 20
  • 3 nights min
  • Child friendly
  • Private garden

from £450 / night

£2,500 / week

Book View

Booked 4 times

from £450 / night

(10) Excellent 

Certificate of Excellence

14

Chesterfield holiday home rental

Derbyshire / Chesterfield

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden

Certificate of Excellence

from £90 / night

£600 / week

Book View

Responds fast!
avg. 17 minutes

Booked 30+ times!

from £90 / night

(7) Excellent 

Certificate of Excellence

14

Holiday cottage in Cutthorpe

Chesterfield / Cutthorpe

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £65 / night

£400 - £500 / week

Book View

Booked 20+ times!

from £65 / night

(9) Excellent 

Certificate of Excellence

20

Holiday cottage in Barlow

Chesterfield / Barlow

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden

Certificate of Excellence

from £70 / night

£490 / week

Book View

Responds fast!
avg. 52 minutes

Booked 10+ times!

from £70 / night

(43) Excellent 

Certificate of Excellence

19

Cottage rental in Ashover

Chesterfield / Ashover

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £78 / night

£335 - £525 / week

Book View

Responds fast!
avg. 1 hour 1 minutes

Booked 30+ times!

from £78 / night

(15) Excellent 

Certificate of Excellence

14

Ashover holiday log cabin rental

Chesterfield / Ashover

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £75 / night

£420 - £910 / week

Book View

Responds fast!
avg. 1 hour 16 minutes

Booked 30+ times!

from £75 / night

(6) Excellent 

9

Cottage rental in Barlow

Chesterfield / Barlow

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from £55 / night

£275 - £570 / week

Book View

Booked 20+ times!

from £55 / night

(28) Excellent 

20

Ashover holiday cottage rental

Chesterfield / Ashover

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
“Fantastic 5* cottage that I would happily recommend to anyone” The location was lovely. Very quiet and pretty. Bakewell was only a 20 minute drive away. The cottage had everything and more that you needed and is done to the highest standards possible. The owners are very helpful. Nothing negative to say about it.

from £95 / night

£665 / week

Book View

Booked 20+ times!

from £95 / night

(3) Excellent 

14

Cutthorpe holiday apartment rental

Chesterfield / Cutthorpe

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

from £90 / night

£500 / week

Book View

Responds fast!
avg. 2 hours 57 minutes

Booked 3 times

from £90 / night

(23) Excellent 

31

Cottage rental in Cutthorpe

Chesterfield / Cutthorpe

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 100 km
  • Child friendly
  • Ask about pets

from £80 / night

£350 - £500 / week

Book View

Responds fast!
avg. 3 hours 10 minutes

Booked 60+ times!

from £80 / night

(43) Excellent 

Certificate of Excellence

21

Ashover holiday cottage rental

Chesterfield / Ashover

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden

Certificate of Excellence

from £90 / night

£385 - £650 / week

Book View

Responds fast!
avg. 1 hour 1 minutes

Booked 40+ times!

from £90 / night

(3) Excellent 

23

Holiday lodge in Chesterfield

Derbyshire / Chesterfield

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden

from £90 / night

£490 / week

Book View

Responds fast!
avg. 3 hours 30 minutes

Booked 7 times

from £90 / night

(20) Excellent 

Certificate of Excellence

26

Holiday boathouse in Chesterfield

Derbyshire / Chesterfield

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Private garden

Certificate of Excellence

from £115 / night

£600 - £860 / week

Book View

Responds fast!
avg. 1 hour 25 minutes

Booked 50+ times!

from £115 / night

(11) Excellent 

26

Cottage letting in Cutthorpe

Chesterfield / Cutthorpe

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly

from £65 / night

£270 - £380 / week

Book View

Responds fast!
avg. 3 hours 10 minutes

Booked 40+ times!

from £65 / night

14

Home rental in Chesterfield

Derbyshire / Chesterfield

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden

from £95 / night

£665 / week

Book View

from £95 / night

(4) Excellent 

Certificate of Excellence

16

Apartment rental in Ashover

Chesterfield / Ashover

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £55 / night

£275 - £350 / week

Book View

Responds fast!
avg. 41 minutes

Booked 20+ times!

from £55 / night

4

Holiday home in Clay Cross

Chesterfield / Clay Cross

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly

from £85 / night

£595 / week

Book View

from £85 / night

(39) Excellent 

Certificate of Excellence

15

Holiday home in Chesterfield

Derbyshire / Chesterfield

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
“Perfect” All rooms well equiped and modern, 3 good sized bedrooms with comfortable beds. Brilliant location (5 min walk to supermarket, and a few minutes drive from the centre of Chesterfield). Plenty of spaces to park in the street. Chatsworth House, Matlock, Bakewell and the Derbyshire Peek District all an easy drive away!

Certificate of Excellence

from £60 / night

£300 - £580 / week

Book View

Responds fast!
avg. 2 hours 22 minutes

Booked 100+ times!

from £60 / night

(3) Average 

7

Holiday apartment rental

Chesterfield / Old Tupton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

from £55 / night

£300 / week

Book View

Responds fast!
avg. 2 hours 37 minutes

Booked 9 times

from £55 / night

(5) Excellent 

9

Barlow holiday cottage rental

Chesterfield / Barlow

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly

from £59 / night

£295 - £610 / week

Book View

Booked 20+ times!

from £59 / night

(3) Very Good 

6

Holiday cottage in Barlow

Chesterfield / Barlow

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets

from £55 / night

£275 - £570 / week

Book View

Booked 10+ times!

from £55 / night

(35) Excellent 

7

Ashover holiday b&b rental

Chesterfield / Ashover

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly

from £80 / night

£480 / week

Book View

Responds fast!
avg. 2 hours 55 minutes

from £80 / night

(1) Excellent 

9

Home letting in Chesterfield

Derbyshire / Chesterfield

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Ask about pets

from £124 / night

£868 / week

Book View

from £124 / night

(1) Excellent 

11

Holiday home in Chesterfield

Derbyshire / Chesterfield

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • Child friendly
  • Ask about pets

from £124 / night

£868 / week

Book View

from £124 / night

(26) Excellent 

Certificate of Excellence

24

Holiday cottage with golf nearby in Ashover

Chesterfield / Ashover

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

Certificate of Excellence

from £80 / night

£560 / week

Book View

Responds fast!
avg. 25 minutes

Booked 30+ times!

from £80 / night

(1)  

13

Holiday home in Chesterfield

Derbyshire / Chesterfield

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

from £92 / night

£644 / week

Book View

Booked 4 times

from £92 / night

(1) Excellent 

7

Barlow holiday barn rental

Chesterfield / Barlow

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Car not necessary

from £50 / night

£350 / week

Book View

Responds fast!
avg. 52 minutes

from £50 / night

7

Holiday home in Chesterfield

Derbyshire / Chesterfield

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden

from £95 / night

£665 / week

Book View

from £95 / night

18

Clowne holiday home rental

Chesterfield / Clowne

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly

from £85 / night

£595 / week

Book View

Responds fast!
avg. 2 hours 25 minutes

from £85 / night

(155) Excellent 

32

Holiday home with indoor pool, golf nearby in New Tupton

Chesterfield / New Tupton

8 22 Min stay varies

  • 8 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £400 / night

£3,250 - £4,990 / week

Enquire View

from £400 / night

(1) Excellent 

8

Home rental in Barlow

Chesterfield / Barlow

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly

from £150 / night

£1,050 / week

Book View

from £150 / night

7

Holymoorside holiday apartment rental

Chesterfield / Holymoorside

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £85 / night

£595 / week

Book View

from £85 / night

11

Holiday home in Barlow

Chesterfield / Barlow

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

from £41 / night

£289 - £631 / week

Enquire View

from £41 / night

18

Holiday home in Barlow

Chesterfield / Barlow

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly

from £42 / night

£298 - £631 / week

Enquire View

from £42 / night

(31) Excellent 

11

Holiday home in Ashover

Chesterfield / Ashover

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £46 / night

£322 - £653 / week

Enquire View

from £46 / night

(4) Excellent 

7

Holiday home in Clay Cross

Chesterfield / Clay Cross

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly

from £44 / night

£309 - £631 / week

Enquire View

from £44 / night

(1) Excellent 

16

Holiday home in New Tupton

Chesterfield / New Tupton

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Private garden

from £136 / night

£958 - £2,389 / week

Enquire View

from £136 / night

16

Holiday home in Holestone Moor

Chesterfield / Holestone Moor

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min

from £40 / night

£283 - £501 / week

Enquire View

from £40 / night

6

Holiday home in Clay Cross

Chesterfield / Clay Cross

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly

from £39 / night

£274 - £460 / week

Enquire View

from £39 / night

(2) Very Good 

8

Holiday home in Holymoorside

Chesterfield / Holymoorside

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly

from £35 / night

£251 - £450 / week

Enquire View

from £35 / night

Top Destination reviews

The Boathouse - secluded lakeside lodge
it was fantastic

it had everything you needed.it was nice and clean and the pub was 100 yards up the road.The host Nigel was very nice. … see more
THE SWALLOWS
Great stay

Fantastic property to stay in while visiting our daughter in Chesterfield. Well equipped with everything (and more) that you could possibly need. Enjoyed the homemade cake and bottle of wine left for us. Barbara and Allan were perfect hosts and were on hand if needed. Our wee dog loved the space to run about outside. Will definitely be backsee more
Hagg Hill Hall
Beautiful house with a fantastic owner

A fantastic few days spent in a beautiful old house, nicely decorated with great bedrooms and lounges as well as a nice spacious pool and two hot tubs. But the highlight was the lord of the manor himself- a wonderful host: friendly, helpful and very entertaining. Would definitely come back and highly recommend it.see more
Fox's Place Holiday Home
Great weekend

A girls weekend, lovely welcome basket on arrival. Beautiful home and had everything you needed. Peter and Carole are very welcoming and made us feel extremely welcome. Defiantly a 5star service … see more
Wood view lodge
Woodview Lodge stay

We had a great stay over the first May Bank Holiday weekend with fantastic weather and plenty to do which,was all close by. The lodge was beautifully kept, very clean and catered for our needs with our disabled son. The owners of the lodge karen and mick were very welcoming and friendly and if we needed anything they were more than happy to help. The lodge is set in the stunning village of cuttthorpe with great views. Lovely and quiet. We enjoyed our stay and would be happy to stay again or recommend to friends.see more
Church View
Brilliant stay

Really enjoyed our weeks stay.. we extended for another 5 days within 2 days. House has everything you need and more. Beautiful garden, good central location in a quiet road. Will be back … see more