Flats in Chesterfield and Guest houses - Holiday Lettings - Holiday Rentals Chesterfield

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942 Holiday homes

(31) 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

from £95 / night

(27) 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. 15 minutes

from £80 / night

(12) 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

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Responds fast!
avg. 3 hours 2 minutes

from £65 / night

(24) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £80 / night

£350 - £500 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

from £80 / night

(12) Excellent 

Certificate of Excellence

17

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. 1 hour 37 minutes

from £70 / night

(4) 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

from £90 / night

(14) 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
“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

Certificate of Excellence

from £110 / night

£770 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from £110 / 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 - £530 / week

Book View

from £55 / night

(4) 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 - £585 / week

Book View

from £55 / night

(22) 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

£425 - £900 / week

Book View

Responds fast!
avg. 1 hour 22 minutes

from £75 / night

(40) 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

£250 - £550 / week

Book View

Responds fast!
avg. 1 hour 59 minutes

from £60 / 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. 29 minutes

from £55 / night

(22) Excellent 

Certificate of Excellence

26

Holiday boathouse in Chesterfield

Derbyshire / Chesterfield

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Private garden

Certificate of Excellence

from £115 / night

£600 - £890 / week

Book View

Responds fast!
avg. 1 hour 27 minutes

from £115 / 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

Responds fast!
avg. 2 hours 44 minutes

from £85 / night

(40) 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 39 minutes

from £80 / 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

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 - £565 / week

Book View

from £59 / night

(4) 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 22 minutes

from £90 / night

14

Holiday home rental

Chesterfield / Hardstoft

9 18 3 nights min

  • 9 bedrooms
  • sleeps 18
  • 3 nights min
  • Child friendly
  • Private garden

from £480 / night

£3,360 / week

Book View

from £480 / 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

(1) Excellent 

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

Responds fast!
avg. 2 hours 49 minutes

from £95 / 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

Responds fast!
avg. 2 hours 44 minutes

from £92 / 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 - £505 / week

Book View

Responds fast!
avg. 39 minutes

from £78 / 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 / week

Book View

Responds fast!
avg. 2 hours 36 minutes

from £65 / 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

Responds fast!
avg. 2 hours 49 minutes

from £95 / 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

(45) Excellent 

Certificate of Excellence

21

Ashover holiday cottage rental

Chesterfield / Ashover

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden

Certificate of Excellence

from £90 / night

£385 - £610 / week

Book View

Responds fast!
avg. 39 minutes

from £90 / 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

(3) Excellent 

Certificate of Excellence

7

Barlow holiday barn rental

Chesterfield / Barlow

1 2 3 nights min

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

Certificate of Excellence

from £50 / night

£350 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £50 / night

(172) Excellent 

38

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

(2) Excellent 

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. 3 hours 30 minutes

from £85 / night

(1) Excellent 

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 £34 / night

£242 - £465 / week

Enquire View

from £34 / night

(3) Very Good 

11

Holiday home in Ashover

Chesterfield / Ashover

3 6 3 nights min

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

from £69 / night

£489 - £1,191 / week

Enquire View

from £69 / 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

11

Holiday home in Barlow

Chesterfield / Barlow

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly

from £43 / night

£304 - £678 / week

Enquire View

from £43 / 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 £128 / night

£902 - £2,524 / week

Enquire View

from £128 / 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 £40 / night

£286 - £631 / week

Enquire View

from £40 / night

11

Holiday home in Barlow

Chesterfield / Barlow

2 4 3 nights min

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

from £40 / night

£286 - £631 / week

Enquire View

from £40 / night

Top Destination reviews

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
Ippleton House (formerly 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
72 Holland Road
Excellent!

Couldn't have asked for a better home to stay in with my friends for the weekend. Had everything we needed including drinking glasses, seating, dining table, microwave etc. Would highly recommend. … see more
Thorntree Lodge Thorntree Farm
Thorn Tree Lodge

My family and I found this brilliant getaway Thorn Tree Lodge, the owners are friendly and welcoming, their Lodge is is close to perfect which we can’t fault. My family and I would recommend this to anyone visiting Ashover. … see more
Budget Accommodation Minutes from Junction 30 M1 Free Parking
Nice stay in low budget

The place is near to chesterfield. Nice house, everything was kept according to our convenience. Good for 8 people. We haven't faced any issue during our stay, rather we enjoyed a lot. Deborah is also very prompt in replying the email. … see more
Hagg Hill Hall
50th birthday celebration

Had an amazing few days with wonderful friends old and new it has everything you could wish for the owner is next door on hand for any queries but he's not intrusive he just let's you get on with having a lovely relaxing time there's plenty of room to chill even with 22 people there. The pool, hot tubs, bed linen and towels were immaculate. The field with sauna and indoor bbq was ideal for our games afternoon,and the huge dining table was amazing we were all able to dine together. The weather was really nice so we spent most of time outdoors but the 2 lounges would be big enough to seat everyone. Although we were only 45 mins away from home we could have been a million miles away it was so peaceful. Would definitely without a doubt re book, Mel the owner even brought us a couple of bottles of wine and some flowers for the birthday girl on our departure lovely touchsee more