Flats in Chesterfield and guest houses – Holiday Lettings - Holiday Rentals Chesterfield

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44 Holiday homes

(7) 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
  • Ask about pets
“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

from £65 / night

£270 - £380 / week

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from £65 / night

(61) Very Good 

20

Holiday barn in Barlow

Chesterfield / Barlow

5 15 Min stay varies

  • 5 bedrooms
  • Sleeps 15
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
“Loved the garden” We stayed here as a group of friends on a weekend walking trip. The house was as described, and ticked all the boxes for us. We especially enjoyed the garden and hot tub and games tables. The large lounge and kitchen was perfect for  …see more

from £200 / night

£1300 - £2820 / week

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from £200 / night

(14) Excellent 

27

Cottage rental in Cutthorpe

Chesterfield / Cutthorpe

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly
  • Ask about pets
“Cottages and B & B of high quality” Whilst this review refers to "The Swallows" we have also stayed in "The Robin" and enjoyed a bed and breakfast room in Barbara and Alan's House. We have been delighted with the quality and standards of accommodatio  …see more

from £75 / night

£350 - £500 / week

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from £75 / night

(3) Average 

7

Holiday apartment rental

Chesterfield / Old Tupton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
This newly constructed brick apartment has been fully furnished to a high standard with TV/DVD, all bedding, cutlery provided. The apartment is sited on Ponderosa Park residential estate located in the Derbyshire village of Old Tupton, a few miles from Chesterfield.The  …see more

from £55 / night

£300 / week

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from £55 / night

(34) Excellent 

22

Ashover holiday cottage rental

Chesterfield / Ashover

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
4 star gold self-catering country cottage in Derbyshire with 3 bedrooms on tranquil lane in small village. Real log fire, private garden and free WiFi. Excellent walking from the doorstep. Chatsworth House within a few miles. Close to Ashover, Chesterfield and Matlock.&  …see more

from £94 / night

£386 - £683 / week

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from £94 / night

(28) Excellent 

16

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  …see more

from £60 / night

£240 - £725 / week

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from £60 / night

(11) Excellent 

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
A wonderful lakeside converted boathouse /log cabin set in its own grounds of over 2 acres with its own private trout lake including boat and pedalo.Situated in a beautiful small hamlet on the border of the historic market town of Chesterfield. Close to Bakewell, Chats  …see more

from £120 / night

£600 - £1100 / week

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from £120 / night

(38) 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
Delightful 4 star stone cottage with fabulous views in a peaceful farming hamlet. Foxglove Cottage sleeps 4 but it is also very popular with couples seeking a rural retreat. Cosy and well-equipped, really comfortable beds and an open log fire. Free WiFi. One pet welcome  …see more

from £82 / night

£352 - £551 / week

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from £82 / 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
One of Three Stone built Cottages set in a sublime Rural Location creating an ideal 'get away from it all' holiday base to explore the stunning Peak District National Park. Furnished and equipped to a very high standard including a Wood burner in the living r  …see more

from £55 / night

£275 - £560 / week

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from £55 / night

(4) Excellent 

9

Barlow holiday cottage rental

Chesterfield / Barlow

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
“Gorgeous cottage in beautiful surroundings” A wonderful little cottage in the most beautiful surroundings! There was a lovely welcome pack for us including a fab bottle of wine. Our weeks stay was to see family and it was the perfect place to do so. T  …see more

from £58 / night

£290 - £585 / week

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from £58 / night

(99) Excellent 

24

Holiday home with indoor pool, golf nearby in New Tupton

Chesterfield / New Tupton

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A grade 2 listed stone manor house dated from the 1600s, sittuated in a beautiful area and grounds , 8 bedrooms , 2 living rooms , large kitchen , summer room , dining room & garden room and large open gardens. Hot Tubs and private indoor heated swimming pool.  …see more

from £735 / night

£2950 - £4695 / week

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from £735 / night

(7) Excellent 

38

Ashover holiday cottage rental

Chesterfield / Ashover

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
“Gorgeous Location, Amazing Hosts” We booked a week at Cavendish Cottage with the intention of taking our son to Alton Towers to celebrate his birthday and to explore the gorgeous surrounding countryside and attractions. The cottage was lovely, and ver  …see more

from £80 / night

£595 - £725 / week

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from £80 / night

(1) Excellent 

20

Holiday cottage in Barlow

Chesterfield / Barlow

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden
This beautiful detached barn conversion has been charmingly renovated, retaining and working with many original features where possible. Tastefully furnished to a very good standard throughout, the open-plan living and kitchen area with its stunning beamed vaulted ceili  …see more

from £60 / night

£420 / week

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from £60 / night

4

Holiday home in Barlow

Chesterfield / Barlow

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
The property is a welcoming mid-terraced cottage located at the heart of Barlow, on the eastern edge of the Peak District National Park. The market town of Chesterfield is a short drive to many nearby attractions. The first feature you will notice...  …see more

from £55 / night

£385 - £595 / week

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from £55 / night

(3) Very Good 

9

Cottage rental in Barlow

Chesterfield / Barlow

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
One of Three Stone built Cottages set in a sublime Rural Location creating an ideal 'get away from it all' holiday base to explore the stunning Peak District National Park. Furnished and equipped to a very high standard including a Wood burner in the living r  …see more

from £55 / night

£275 - £560 / week

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from £55 / night

23

Holiday lodge in Chesterfield

Derbyshire / Chesterfield

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Carpenters Lodge is situated in the village of Marsh Lane on the edge of the Peak District and offers high quality self-catering accommodation for up to four people. The Lodge is attached to our recently recovered barn conversion, however is independent from the main ba  …see more

from £90 / night

£490 / week

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from £90 / night

(20) Excellent 

18

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

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from £80 / night

4

Holiday home in Clay Cross

Chesterfield / Clay Cross

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
A good 3 bedroom mid terraced property benefiting from off street parking. Large fitted breakfasting/dining kitchen, spacious lounge with feature fireplace/bedroom 4. Three good-sized bedrooms to the first floor. Gas fired Central heating and double glazing. The propert  …see more

from £85 / night

£595 / week

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from £85 / night

(2) Average 

11

Holiday home in Chesterfield

Derbyshire / Chesterfield

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly
Lovely stone built country cottage, in friendly village set in glorious countryside edge of Peak District. " to 4 bedrooms, sleeping 2 to 8 + cot(s). Baby/ child/ pet friendly. Close all amenities, easy reach Chatsworth, Hardwick, Haddon, Sheffield, Derby, Manches  …see more

from £149 / night

£950 / week

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from £149 / night

15

Home rental in Chesterfield

Derbyshire / Chesterfield

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Private garden
Fully refurbished detached home having 3 double bedrooms, 2 reception, 2 x w/cs, large garage and garden. The property has easy access into both Chesterfield, Sheffield and the peak district. Kitchen; 9 x 7' 4" Lounge; 12'5 x 11' 8" Dining room  …see more

from £85 / night

£595 / week

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from £85 / night

(1)  

13

Holiday home in Chesterfield

Derbyshire / Chesterfield

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
This is a large 3 bed semi-detached property with off street parking and a garden. The property has both kitchen and a 1st floor bathroom off-shot kitchen extension, it  …see more

from £82 / night

£574 / week

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from £82 / night

(18) Excellent 

7

Ashover holiday b&b rental

Chesterfield / Ashover

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
Set in a quiet rural location close to the Peak District, Oaks Lane Farm B&B provides the perfect location for a relaxing break, visiting local attractions including Chatsworth House or the more rugged landscape of the High Peak. Bakewell is just 5 miles away.  …see more

from £80 / night

£480 / week

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from £80 / 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
The Annexe is a stunning one bedroomed apartment set in picturesque grounds of Kneese Croft House. Tucked away in the country settings of Holymoorside, Chesterfield The Annexe is perfect for a peaceful getaway. There are also road links to Matlock and the Peak District  …see more

from £85 / night

£595 / week

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from £85 / night

4

Holiday home in Barlow

Chesterfield / Barlow

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Enjoying an idyllic position in the peaceful rural village of Barlow, Mulberry Cottage is a lovely property for those seeking a taste of village life amidst the outstanding natural beauty of the Peak District. Surrounded by excellent walking trails t...  …see more

from £62 / night

£430 - £665 / week

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from £62 / night

4

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
Located only a mile from Chesterfield, guests are never far away from a wide selection of eateries and shops. A day spent bargain hunting at Chesterfield Market is a must, and the famous crooked church spire is well worth a visit. A short drive west...  …see more

from £311 / night

£2175 - £2860 / week

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from £311 / night

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
Two bedroom ground floor apartment..wheel chair access..open views to front..garden view to both bedrooms..large open plan kitchen/lounge/diner.. All furniture and decoration to high standard..very comfortable and light through out. Lovely decked area with seating and l  …see more

from £75 / night

£350 - £400 / week

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from £75 / night

4

Holiday home in Chesterfield

Derbyshire / Chesterfield

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Private garden
A good 3 or 4 bedroom semi detached property benefiting from off-street parking. Briefly the property has an entrance hallway leading through to both the open plan dining kitchen with patio doors leading out to the garden and bay fronted lounge/bedroom 4 and w/c. Upsta  …see more

from £90 / night

£630 / week

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from £90 / night

11

Holiday home in Chesterfield

Derbyshire / Chesterfield

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • Child friendly
  • Ask about pets
A modernised and spacious 5 bed property which benefits from having 2 shower rooms a lovely open plan dining kitchen. The area has good access links to the M1, Derbyshire countryside and the Peak District, the town of Chesterfield and Sheffield City Centre. Ample free p  …see more

from £124 / night

£868 / week

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from £124 / night

9

Home letting in Chesterfield

Derbyshire / Chesterfield

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Ask about pets
A refurbished stone built and spacious three bedroom mid terraced property. The area has good access to the M1 motorway, Derbyshire countryside, the Peak District and both Chesterfied Town and Sheffield City Centre. The property is also in walking distance to the propos  …see more

from £124 / night

£868 / week

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from £124 / night

(2) Excellent 

7

Chesterfield / Ashover

2 4 3 nights min

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

 …see more

from £43 / night

£296 - £773 / week

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from £43 / night

11

Chesterfield / Ashover

2 4 3 nights min

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

 …see more

from £55 / night

£380 - £662 / week

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from £55 / night

6

Chesterfield / Ashover

1 2 3 nights min

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

 …see more

from £37 / night

£254 - £587 / week

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from £37 / night

11

Derbyshire / Chesterfield

2 5 3 nights min

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

 …see more

from £47 / night

£327 - £626 / week

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from £47 / night

(26) Excellent 

11

Chesterfield / Ashover

2 4 3 nights min

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

 …see more

from £44 / night

£306 - £750 / week

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from £44 / night

19

Chesterfield / Clay Cross

2 3 3 nights min

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

 …see more

from £48 / night

£330 - £588 / week

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from £48 / night

(3) Excellent 

22

Chesterfield / Ashover

4 8 3 nights min

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

 …see more

from £83 / night

£577 - £1275 / week

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from £83 / night

(1) Excellent 

16

Derbyshire / Chesterfield

5 10 3 nights min

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

 …see more

from £126 / night

£882 - £1851 / week

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from £126 / night

(6) Very Good 

16

Chesterfield / Ashover

2 4 3 nights min

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

 …see more

from £45 / night

£313 - £598 / week

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from £45 / night

18

Derbyshire / Chesterfield

2 4 3 nights min

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

 …see more

from £45 / night

£313 - £598 / week

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from £45 / night

(5) Average 

8

Derbyshire / Chesterfield

1 2 3 nights min

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

 …see more

from £31 / night

£214 - £520 / week

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from £31 / night

Top Destination reviews

THE SWALLOWS
Great cottage

Fantastic cottage - very well equipped and homely. Barbara was very welcoming and the welcome cake, milk and wine was much appreciated - we would highly recommend - very good location. Thank you. … see more
3 The Rumblings
Gorgeous cottage in beautiful surroundings

A wonderful little cottage in the most beautiful surroundings! There was a lovely welcome pack for us including a fab bottle of wine. Our weeks stay was to see family and it was the perfect place to do so. The house is beautiful and we will definitel … see more
Old Robin Hood Grade II listed
Birthday

We had a wonderful weekend stay at the Old Robin Hood with friends for a 40th Birthday. The cottage was fully equipped and the owner was very friendly and helpful. We would highly recommend he cottage and would definitely use again for future get … see more
Cavendish Cottage Ashover Derbyshire dog friendly
Fantastic Cottage

This is a beautiful place to stay. All your needs are catered for with quality furnishings and high class fixtures. The kitchen has everything you need, dishwasher, washing machine etc. The owners are very friendly and very helpful. We found the fenc … see more