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

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998 Holiday homes

(9) 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
“Christmas Break” Fox,s Place is an exceptional holiday home. We spent five nights there with my sister and her husband to celebrate Christmas together. We were met by Peter who showed us around the very clean and well decorated house. They had even de
…see more

Certificate of Excellence

from £90 / night

£600 / week

Book View

Responds fast!
avg. 11 minutes

from £90 / 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

from £59 / night

14

Holiday home rental

Chesterfield / Hardstoft

9 20 Min stay varies

  • 9 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
  • Private garden

from £350 / night

£1,200 - £2,500 / week

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from £350 / 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

from £55 / night

(37) 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
“Excellent accommodation and an excellent rate.” We booked church view as a base to explore the Peak District and we couldn't fault it. Although not a 'cottage' as we had originally planned it was well worth the money - all other letting a hiked their
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Certificate of Excellence

from £60 / night

£250 - £580 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from £60 / night

(20) 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
“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

Certificate of Excellence

from £110 / night

£600 - £860 / week

Book View

Responds fast!
avg. 54 minutes

from £110 / night

(7) 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. 1 hour 4 minutes

from £70 / night

(5) 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 £60 / night

£375 - £480 / week

Book View

from £60 / night

(24) 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
“Beautiful!” Loved our stay at Cavendish cottage. Its a beautiful cottage, with lovely walks nearby! Will definitely be returning! Thanks for a beautiful break!
…see more

from £93 / night

£651 / week

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from £93 / night

(41) Excellent 

21

Ashover holiday cottage rental

Chesterfield / Ashover

3 6 Min stay varies

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

from £90 / night

£385 - £650 / week

Book View

Responds fast!
avg. 1 hour 13 minutes

from £90 / night

(12) 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
“Perfection!” I stayed here over new year with my family and it was absolutely perfect. The place was beautiful. A lovely location with stunning accommodation made this the perfect get away for a family trip. The lodge is beautifully presented and very
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Certificate of Excellence

from £85 / night

£750 - £910 / week

Book View

Responds fast!
avg. 1 hour 13 minutes

from £85 / 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

from £55 / night

(1) 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 38 minutes

from £90 / night

(23) Excellent 

Certificate of Excellence

26

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
“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 host
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Certificate of Excellence

from £80 / night

£350 - £500 / week

Book View

Responds fast!
avg. 2 hours 2 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

Responds fast!
avg. 2 hours 39 minutes

from £55 / night

(43) Excellent 

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

from £78 / night

£335 - £525 / week

Book View

Responds fast!
avg. 1 hour 13 minutes

from £78 / 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

from £92 / night

(11) Excellent 

Certificate of Excellence

27

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
“One man and his two dogs” I had a weeks stay with my two Yorkies in Sept 2011 and i could not have been better treated by Mr and Mrs Campbell. They made sure all my needs were met before I arrived and while i was staying in The Robins, My two Yorkie
…see more

Certificate of Excellence

from £65 / night

£270 - £380 / week

Book View

Responds fast!
avg. 2 hours 2 minutes

from £65 / night

(25) Excellent 

24

Holiday cottage with golf nearby in Ashover

Chesterfield / Ashover

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
“Had a fantastic time in a lovely cottage” This is a great base for visiting this area and The Retreat really felt like a home from home, it was warm and cosy and had everything you could need. The owners were very accommodating when we had to change
…see more

from £80 / night

£560 / week

Book View

Responds fast!
avg. 49 minutes

from £80 / night

(32) 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. 3 hours 28 minutes

from £80 / night

14

Holiday home with indoor pool in Chesterfield

Derbyshire / Chesterfield

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly

from £321 / night

£2,242 - £3,064 / week

Enquire View

from £321 / night

(4) Excellent 

16

Apartment rental in Ashover

Chesterfield / Ashover

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
“Amazing!” My family and I had a great weekend staying in Isabel’s appartment. We had all the space we needed and more! My son especially loved the fish pond and the hens! We are all looking forward to staying there again in the new year!
…see more

from £49 / night

£245 - £305 / week

Book View

Responds fast!
avg. 51 minutes

from £49 / night

19

Holiday cottage in Holymoorside

Chesterfield / Holymoorside

2 4 2 nights min

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

from £70 / night

£490 / week

Book View

Responds fast!
avg. 3 hours 20 minutes

from £70 / night

16

Holiday home in Barlow

Chesterfield / Barlow

2 4 7 nights min

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

from £64 / night

£445 - £713 / week

Enquire View

from £64 / night

(2) 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

from £90 / night

15

Holiday home in Barlow

Chesterfield / Barlow

3 4 7 nights min

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

from £57 / night

£399 - £638 / week

Enquire View

from £57 / 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

16

Holiday home in Barlow

Chesterfield / Barlow

2 4 7 nights min

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

from £57 / night

£399 - £638 / week

Enquire View

from £57 / 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 

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

(147) 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

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

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

(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

(1) Excellent 

19

Holiday home in Clay Cross

Chesterfield / Clay Cross

2 3 3 nights min

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

from £50 / night

£349 - £674 / week

Enquire View

from £50 / 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 £41 / night

£286 - £562 / week

Enquire View

from £41 / 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

£286 - £570 / week

Enquire View

from £41 / 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 £45 / night

£309 - £615 / week

Enquire View

from £45 / night

(30) Excellent 

11

Holiday home in Ashover

Chesterfield / Ashover

2 4 3 nights min

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

from £46 / night

£322 - £653 / week

Enquire View

from £46 / night

Top Destination reviews

Columbine Cottage - Wildflower Cottages - Ashover holiday rental
Amazing stay in a perfect cottage

We have recently returned from a 3 night stay in columbine cottage and it was fantastic! The cottage was extremely clean, well maintained and well equipped. It has a gorgeous rustic charm with an open fire and has a nice cosy open plan feel making it spacious and welcoming. The owner Sue was friendly and welcoming and all communications have been a pleasure. We will certainly be back!see more
The Boathouse - secluded lakeside lodge
Gorgeous relaxing 2 day break for my partners birthday.

We have checked out of here this morning after an amazing stay with my 3 year old son and my boyfriend who's birthday was on Thursday. This was a break for all of us to enjoy and we loved it. It was so relaxing and my little boy loved the lake and we spent a lot of time in the jacuzzi. When we arrived Nigel was very friendly and had a bottle of prosecco chilling in the fridge for us. The lodge is decorated really nicely and is very homely. The beds are very comfy and my son slept on the fold out bed in the open plan living room/kitchen which he must have found very comfy because the first morning he slept in later than he usually would at home! There was lots of things close by, takeaways, pubs, restaurants and Nigel gave us information on these when we got there. And he was always a phone call away if we needed anything. The lodge has things like wifi and now tv. On the first night we had a BBQ in the sun and spent time in the hot tub. And the following night we had a Chinese from the takeaway, had a drink in the hot tub and then watched the now tv box. Overall we had a really relaxing time. My son never once got bored and he didn't want to go home! And most importantly my boyfriend enjoyed his birthday! Thank you to Nigel for a lovely stay in a lovely area. We would definitely stay again!see more
Fox's Place Holiday Home
Fantastic owners, beautiful house.

Carole and Peter were fabulous from the start of my booking until leaving their beautiful home at the end of our trip. The house and gardens are beautifully presented and came with everything we needed for our stay. I will definitely be staying here again and would recommend Fox's Place to anybody that needs a place to stay in Chesterfield.see more
Dog Friendly Spacious 2 Bedroom Apartment
clean,quiet, although dog friendly unable to let in garden unattended.

nice location, very quiet, easy to get to attractions matlock, castleton etc. very clean, all ammenities needed. only draw back no fence or gate between rental and owners home, on edge when dog out side. Owner very friendly. beautiful garden. … see more
Thorntree Lodge Thorntree Farm
A fantastic venue - wonderfully comfy and cozy

We were very impressed with the lodge which was extremely comfortable and cozy. It is in a great location, being conveniant for walks , attractions and eating out . The owners were very friendly and helpful and we wouldn't hesitate to use the lodge as a base for future breaks or to recommend the accomadation to others.see more
Runner Duck Cottage
Absolutely perfect, exactly as described....spotlessly clean and great attention to detail.

A super little cottage, exceeded all expectations. The owners were welcoming and friendly but not intrusive. A fabulous area for walking and lovely views from the vicinity. … see more