Long term rentals Chesterfield | Holiday Lettings

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  • Ashover (8)
  • Barlow (5)
  • Clay Cross (3)
  • Cutthorpe (5)
  • New Tupton (2)
  • Old Tupton (1)
  • Palterton (1)
  • Stonedge (3)

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43 Holiday homes

(26) Excellent 

16

Church View - Chesterfield house sleeps 6

Derbyshire / Chesterfield

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Church View is located on the outskirts of the historic market town of Chesterfield and the edge of the Peak district. It is ideally suited for families and couples alike who are looking to explore the Peak district and the Nottinghamshire countryside including Sherwood  …see more

from £65 / night

£325 - £725 / week

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from £65 / night

(36) Excellent 

19

Foxglove Cottage - Ashover near Chesterfield - Ashover cottage sleeps 4

Chesterfield / Ashover

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Foxglove Cottage is full of character and is furnished and equipped to a high standard whilst retaining many original features. Foxglove sleeps four but we've discovered that it is a particular favourite with couples. This 4 star stone cottage is on a quiet, private  …see more

from £81 / night

£347 - £551 / week

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from £81 / night

(12) Excellent 

27

THE SWALLOWS - Cutthorpe cottage sleeps 5

Chesterfield / Cutthorpe

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 100 km
  • Child friendly
  • Ask about pets
Originally built over 200 year ago, and used as a barn until 2000, this award winning environmentally-friendly, 4 star stone cottage, retains many original features plus the comforts of modern living. It is furnished and equipped to a high standard. The accommodat  …see more

from £77 / night

£330 - £480 / week

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from £77 / night

(31) Excellent 

22

Columbine Cottage - Ashover holiday rental - Ashover cottage sleeps 6

Chesterfield / Ashover

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
This lovely cottage has three bedrooms and sleeps up to six people. It is on a peaceful, private lane in the small farming hamlet of Alton, in the award-winning parish of Ashover and is on the eastern side of the Peak District. There are fantastic views across the valle  …see more

from £93 / night

£386 - £683 / week

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from £93 / night

(3) Good 

7

50 Ponderosa Park - Old Tupton apartment sleeps 2

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

(56) Very Good 

20

Old Robin Hood Grade II listed - Barlow barn sleeps 15

Chesterfield / Barlow

5 15 Min stay varies

  • 5 bedrooms
  • Sleeps 15
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
This is a beautifully restored coach house. The original stone floor is evident and heated throughout the downstairs via geothermal heating. It is a spacious house and very suitable for large groups. Beautiful views over the Peak District.There is a large wooden beame  …see more

from £200 / night

£1000 - £2350 / week

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from £200 / night

20

Old Barn Conversion Holiday Let - Barlow cottage sleeps 4

Chesterfield / Barlow

2 4 Min stay varies

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

(11) Excellent 

26

The Boathouse - secluded lakeside lodge - Chesterfield boathouse sleeps 4

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 £115 / night

£600 - £1010 / week

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from £115 / night

(3) Very Good 

9

2 The Rumblings - Barlow cottage sleeps 4

Chesterfield / Barlow

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Situated on the edge of The Peak District National Park the Rumblings make an ideal holiday base for exploration through any means. With footpaths on the door step instead of taking the car guests can take off using their own steam. The minor road network close to the p  …see more

from £55 / night

£273 - £490 / week

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from £55 / night

25

Carpenters Lodge - Chesterfield lodge sleeps 4

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

(3) Very Good 

6

1 The Rumblings - Barlow cottage sleeps 4

Chesterfield / Barlow

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets
Situated on the edge of The Peak District National Park the Rumblings make an ideal holiday base for exploration through any means. With footpaths on the door step instead of taking the car guests can take off using their own steam. The minor road network close to the p  …see more

from £55 / night

£273 - £490 / week

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from £55 / night

(4) Excellent 

38

Cavendish Cottage Ashover Derbyshire dog friendly - Ashover cottage sleeps 4

Chesterfield / Ashover

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Discover the secret that is Cavendish cottage, a recently renovated rural luxury cottage situated on the edge of the Peak District National Park. This cosy retreat with a light and airy feel is beautifully presented. The front door opens into an open plan living area wh  …see more

from £71 / night

£370 - £650 / week

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from £71 / night

(7) Excellent 

26

THE ROBINS - Cutthorpe cottage sleeps 2

Chesterfield / Cutthorpe

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 100 km
  • Child friendly
  • Ask about pets
The Robins is a cosy retreat for couples or small families who love the countryside. Surrounded by beautiful countryside, with walks from the door, a large garden and a pub/restaurant across the road, this could offer that relaxing escape you need.Originally built over  …see more

from £60 / night

£260 - £370 / week

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from £60 / night

(2) Very Good 

9

3 The Rumblings - Barlow cottage sleeps 5

Chesterfield / Barlow

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
Situated on the edge of The Peak District National Park the Rumblings make an ideal holiday base for exploration through any means. With footpaths on the door step instead of taking the car guests can take off using their own steam. The minor road network close to the p  …see more

from £55 / night

£273 - £490 / week

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from £55 / night

(20) Excellent 

18

The Retreat - Ashover cottage sleeps 2

Chesterfield / Ashover

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
This thoughtfully converted, upside-down, end-of-terrace holiday cottage has a traditional feel to it and both the living room and bedroom have a Juliet balcony with views over the Amber Valley. Set in the centre of the beautiful conservation village of Ashover in Derby  …see more

from £80 / night

£560 / week

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from £80 / night

6

THE RUMBLINGS 1 - Chesterfield house sleeps 4

Derbyshire / Chesterfield

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
Situated on the edge of The Peak District National Park these terraced stone barn conversions (refs 27400, 27401 and 27402) make an ideal holiday base. Furnished and equipped to a very good standard, they are ideally situated in a rural location, great for a get away fr  …see more

from £45 / night

£310 - £527 / week

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from £45 / night

9

THE RUMBLINGS 2 - Chesterfield house sleeps 4

Derbyshire / Chesterfield

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
Situated on the edge of The Peak District National Park these terraced stone barn conversions (refs 27400, 27401 and 27402) make an ideal holiday base. Furnished and equipped to a very good standard, they are ideally situated in a rural location, great for a get away fr  …see more

from £45 / night

£310 - £527 / week

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from £45 / night

(3) Excellent 

23

The Pottery Flat - Chesterfield apartment sleeps 5

Derbyshire / Chesterfield

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 137 km
  • Child friendly
  • Car not necessary
The Pottery Flat is an apartment accessed by a short flight of stairs. The property is three star gold, self catering approved by Visit England. The flat has a fully equipped kitchen (including up to date recipe books) and a table for sitting down to eat breakfast in co  …see more

from £70 / night

£480 - £600 / week

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from £70 / night

11

THE OLD COACH HOUSE - Chesterfield house sleeps 4

Derbyshire / Chesterfield

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
This former coach house is set within the peaceful and historic village of Scarcliffe. Standing detached, the accommodation offers the perfect holiday base for walking, cycling, shopping at Meadow Hall, McArthur Glen or visiting one of the many attractions this area has  …see more

from £40 / night

£275 - £599 / week

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from £40 / night

(85) Excellent 

24

Hagg Hill Hall - New Tupton house sleeps 18

Chesterfield / New Tupton

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Hagg Hill House is filled with a wealth of antiques and luxurious furniture, 2 living areas with large sofas & flat screen TV's, large dining room and garden room that both easily seat 18 . The kitchen has a large table that easily seats 10, plus a large 4 oven AGA &  …see more

from £685 / night

£2750 - £4695 / week

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from £685 / night

9

THE RUMBLINGS 3 - Chesterfield house sleeps 5

Derbyshire / Chesterfield

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
Situated on the edge of The Peak District National Park these terraced stone barn conversions (refs 27400, 27401 and 27402) make an ideal holiday base. Furnished and equipped to a very good standard, they are ideally situated in a rural location, great for a get away fr  …see more

from £47 / night

£328 - £379 / week

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from £47 / night

16

PK936 Cottage in Rowsley - Stonedge house sleeps 7

Chesterfield / Stonedge

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Pet friendly
Stanton Lodge is a spacious and handsome stone cottage in the village of Rowsley, close to the Chatsworth Estate. This property offers comfortable accommodation with attractive and sunny garden areas.The cottage is ideally located to enjoy the splendour of the Peak Dist  …see more

from £93 / night

£645 - £840 / week

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from £93 / night

(2) Good 

11

Aaren House, 35, Holymoor Rd. - Chesterfield house sleeps 8

Derbyshire / Chesterfield

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly
A warm welcome awaits you in our quaint country house, very flexible, very spacious & all mod. cons., incl. Freeview TV. Relaxed quiet village, but easy to reach all of Peak District, Yorkshire Moors, Cheshire, culture in Chesterfield, Sheffield, Manchester, Derby, Nott  …see more

from £149 / night

£950 / week

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from £149 / night

15

72 Holland Road - Chesterfield house sleeps 8

Derbyshire / Chesterfield

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 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; 12'5 x 11'8" Bed 1;  …see more

from £100 / night

£600 - £1440 / week

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from £100 / night

(12) Excellent 

7

Oaks Lane Farm B&B, Ashover, Derbyshire, England - Ashover b&b sleeps 3

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. Wit  …see more

from £80 / night

£480 / week

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from £80 / night

12

PK762 Cottage in Chesterfield - New Tupton house sleeps 4

Chesterfield / New Tupton

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Cutthorpe is a small and tranquil village on the eastern edge of the Peak District National Park. Spread over three miles, it includes Linacre Reservoirs with its picturesque bluebell woods and many walking trails. With popular Chesterfield less than 15 minutes away by  …see more

from £54 / night

£375 - £595 / week

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from £54 / night

5

Gardener's Cottage - Clay Cross cottage sleeps 3

Chesterfield / Clay Cross

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
  • Private garden
Gardener's Cottage is a lovely holiday home, set within two acres of grounds with Alma House, a Victorian gentleman's residence dating back to the 1875. The cottage has two bedrooms, a room with a king-size bed on the first floor than can be unzipped into twin  …see more

from £47 / night

£323 - £539 / week

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from £47 / night

7

The Old Blacksmiths - Clay Cross cottage sleeps 4

Chesterfield / Clay Cross

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
The Old Blacksmiths is a beautiful stone cottage on the edge of the lovely village of Ashover in the Peak District and can sleep four people. There is a king-size double bedroom with an en-suite shower room, a twin bedroom with an en-suite shower room, an open plan livi  …see more

from £42 / night

£290 - £498 / week

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from £42 / night

53

Manor House - Chesterfield cottage sleeps 10

Derbyshire / Chesterfield

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Private garden
Manor House is a marvellous ground floor, detached cottage on the outskirts of Chesterfield in Derbyshire. Boasting five bedrooms, including three en-suite double rooms, a double and a twin room and two further bathrooms, the property can sleep up to ten people. The cot  …see more

from £123 / night

£861 - £1661 / week

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from £123 / night

6

The Byre - Clay Cross cottage sleeps 2

Chesterfield / Clay Cross

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
  • Private garden
The Byre is a cosy retreat on the edge of the lovely village of Ashover in the Peak District and can sleep two people. There is a super king-size double bedroom (zip/link, can be twin on request), a bathroom, an open plan living area with a kitchen, a dining area and a  …see more

from £36 / night

£249 - £364 / week

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from £36 / night

14

Wood view lodge - Cutthorpe apartment sleeps 4

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

8

YEW TREE BOTHY - Chesterfield house sleeps 2

Derbyshire / Chesterfield

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
Yew Tree Bothy, which forms part of the owners' home, provides small but comfortable holiday accommodation which is ideally located on the edge of the Peak District National Park. Surrounded by 30 acres of land, the property has its own sitting-out area from which  …see more

from £37 / night

£257 - £507 / week

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from £37 / night

9

20 Holland Road - Chesterfield house sleeps 7

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

5

Leveret - Stonedge cottage sleeps 2

Chesterfield / Stonedge

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Private garden
Leveret is a first floor cottage situated one mile from the small village of Holymoorside, near Chesterfield in the Peak District National Park. This cottage sleeps two people and has a double bedroom, a bathroom and an open plan living area with kitchen, dining area an  …see more

from £43 / night

£298 - £496 / week

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from £43 / night

11

William Street North - Chesterfield house sleeps 13

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

16

PK880 Cottage in Chesterfield - Ashover house sleeps 10

Chesterfield / Ashover

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 will bring you to t  …see more

from £192 / night

£1340 - £1810 / week

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from £192 / night

10

Spinney - Stonedge cottage sleeps 2

Chesterfield / Stonedge

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Private garden
Spinney is a delightful ground floor cottage situated one mile from the small village of Holymoorside, 4.5 miles from Chesterfield. This cottage sleeps two people and has a double bedroom, a bathroom and an open plan living area with kitchen, dining area and sitting are  …see more

from £43 / night

£298 - £496 / week

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from £43 / night

9

14137 - Castle Cottage - Palterton house sleeps 7

Chesterfield / Palterton

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Pet friendly
Castle Cottage is situated in Palterton in Derbyshire. The cottage sleeps seven people and has one king-size double bedroom with an additional single folding bed, one twin bedroom, a ground floor shower room, a bathroom, a fitted kitchen with dining area and a sitting r  …see more

from £40 / night

£274 - £491 / week

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from £40 / night

15

Acorn Cottage - Ashover house sleeps 4

Chesterfield / Ashover

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
  • Private garden
Acorn Cottage is a stone-built Peak District cottage, located on the owners' working smallholding in the tiny hamlet of Brockhurst, one mile from the pretty village of Ashover in Derbyshire. The cottage can sleep four people in two bedrooms - one double and one twi  …see more

from £43 / night

£299 - £541 / week

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from £43 / night

(4) Excellent 

12

Stubben Barn - Ashover cottage sleeps 4

Chesterfield / Ashover

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Suitable for children age 5+
  • Private garden
This delightful single-storey detached cottage is well-situated in a lovely position as part of the rural hamlet of Handley. This property offers wonderful countryside views towards Ogston Reservoir and provides warm, welcoming accommodation for its guests. The cottage  …see more

from £47 / night

£325 - £584 / week

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from £47 / night

Top Destination reviews

Cavendish Cottage Ashover Derbyshire dog friendly
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 very recently finished so everything … see more
Old Robin Hood Grade II listed
Well equipped house in an idyllic location.

We stayed here for 2 weeks with extended family ranging from 8 months to 60 years old. Very well equipped house which really did cater for all our needs. Outstanding views in an idyllic location. Easy access to Sheffield and surrounding areas in the … see more

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