Long term rentals Chesterfield | Holiday Lettings

Close

View larger map

Price per night

to

Bedrooms

Bathrooms

Location

  • United Kingdom
  • England
  • Derbyshire
  • Chesterfield
  • All locations
  • Ashover (16)
  • Barlow (4)
  • Clay Cross (4)
  • Cutthorpe (4)
  • Holymoorside (2)
  • New Tupton (2)
  • Old Tupton (1)
  • Palterton (1)
  • Stonedge (3)

More

Less

Also consider

Cottages Cornwall
2983 properties
Apartments Greater London
941 properties
Cottages Cumbria / Lake District
940 properties
Houses Devon
2810 properties
Cottages Central England / Cotswolds
940 properties
Houses Dorset
819 properties
Houses Isle of Wight
507 properties
Cottages Peak District / Derbyshire
460 properties
Houses Somerset
610 properties
Houses Kent
557 properties
Houses Sussex
770 properties
Houses Norfolk
1023 properties
Cottages Isle of Man
11 properties
Northumberland
640 properties
Houses Yorkshire / Yorkshire Dales
1496 properties
Coastal Cottages
222 properties
Ashover
8 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

57 Holiday homes

(11) Excellent 

1 / 27

THE SWALLOWS - Cutthorpe cottage sleeps 5

Chesterfield / Cutthorpe

3 5 3 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 100 km; Child friendly ; Car advised;
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

Book Book View

from £77 / night

(3) Excellent 

1 / 23

The Pottery Flat - Chesterfield apartment sleeps 5

Derbyshire / Chesterfield

3 5 2 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: 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

Book Book View

from £70 / night

(10) Excellent 

1 / 26

The Boathouse - secluded lakeside lodge - Chesterfield boathouse sleeps 4

Derbyshire / Chesterfield

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; Car advised;
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 - £960 / week

Book Book View

from £115 / night

(81) Excellent 

1 / 24

Hagg Hill Hall - New Tupton house sleeps 18

Chesterfield / New Tupton

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
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

Enquire Enquire View

from £685 / night

(33) Excellent 

1 / 19

Foxglove Cottage - Ashover near Chesterfield

Chesterfield / Ashover

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Car essential; Pet friendly;
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

Book Book View

from £81 / night

(25) Excellent 

1 / 16

Church View - Chesterfield house sleeps 6

Derbyshire / Chesterfield

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; Car advised; Ask about pets;
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

Book Book View

from £65 / night

(6) Excellent 

1 / 26

THE ROBINS - Cutthorpe cottage sleeps 2

Chesterfield / Cutthorpe

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 100 km; Child friendly ; Car advised;
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

Book Book View

from £60 / night

(2) Very Good 

1 / 8

Chesterfield / Holymoorside

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £43 / night

£298 - £507 / week

Enquire Enquire View

from £43 / night

(54) Very Good 

1 / 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
Key info: Child friendly ; Car advised; Ask about pets;
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

Book Book View

from £200 / night

1 / 25

Carpenters Lodge - Chesterfield lodge sleeps 4

Derbyshire / Chesterfield

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; No pets allowed; 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

£480 - £490 / week

Book Book View

from £90 / night

(3) Good 

1 / 7

50 Ponderosa Park - Old Tupton apartment sleeps 2

Chesterfield / Old Tupton

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Not suitable for children; No pets allowed;
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

Book Book View

from £55 / night

(28) Excellent 

1 / 22

Columbine Cottage - Ashover holiday rental

Chesterfield / Ashover

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; Car essential; No pets allowed;
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 £90 / night

£386 - £683 / week

Book Book View

from £90 / night

(1) Very Good 

1 / 9

2 The Rumblings - Barlow cottage sleeps 4

Chesterfield / Barlow

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Car advised; No pets allowed;
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

Book Book View

from £55 / night

(1) Excellent 

1 / 9

3 The Rumblings - Barlow cottage sleeps 5

Chesterfield / Barlow

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Child friendly ; Car advised; No pets allowed;
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

Book Book View

from £55 / night

(2) Excellent 

1 / 24

Spinney Top Cottage - Chesterfield cottage sleeps 4

Derbyshire / Chesterfield

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Ask about pets;
Deceptively spacious ground-floor Derbyshire cottage, a short drive from Chatsworth, Haddon & Hardwick Halls and The Matlocks.Thecottage is adjacent to the owner's home and grounds, set in a rural location, with views towards Chatsworth & The Peak District  …see more

from £50 / night

£285 - £485 / week

Book Book View

from £50 / night

(2) Good 

1 / 11

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

Derbyshire / Chesterfield

3 8 3 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Child friendly ; Car advised; 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

Book Book View

from £149 / night

1 / 15

72 Holland Road - Chesterfield house sleeps 8

Derbyshire / Chesterfield

3 8 2 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Child friendly ; No pets allowed; 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

Book Book View

from £100 / night

(20) Excellent 

1 / 18

The Retreat - Ashover cottage sleeps 2

Chesterfield / Ashover

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Not suitable for children; No pets allowed;
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

Book Book View

from £80 / night

1 / 9

THE RUMBLINGS 2 - Chesterfield house sleeps 4

Derbyshire / Chesterfield

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Not suitable for children; No pets allowed;
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

Enquire Enquire View

from £45 / night

1 / 9

Chesterfield / Holymoorside

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £43 / night

£298 - £507 / week

Enquire Enquire View

from £43 / night

(3) Very Good 

1 / 19

The Old Byre - Cutthorpe cottage sleeps 6

Chesterfield / Cutthorpe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; Car advised; Pet friendly;
The Old Byre is a superb cottage created out of a mellow brick barn that provides really classy accommodation. It offers lots and lots of luxury with a fantastic lounge, superb kitchen, lovely bedrooms with en-suite bathrooms and a glowing log burning stove to top it al  …see more

from £160 / night

£672 - £1021 / week

Enquire Enquire View

from £160 / night

1 / 9

THE RUMBLINGS 3 - Chesterfield house sleeps 5

Derbyshire / Chesterfield

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Not suitable for children; No pets allowed;
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 - £561 / week

Enquire Enquire View

from £47 / night

1 / 38

Cavendish Cottage Ashover Derbyshire dog friendly

Chesterfield / Ashover

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: 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

Book Book View

from £71 / night

1 / 11

THE OLD COACH HOUSE - Chesterfield house sleeps 4

Derbyshire / Chesterfield

1 4 7 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Not suitable for children; No pets allowed;
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

Enquire Enquire View

from £40 / night

(7) Excellent 

1 / 7

Oaks Lane Farm B&B, Ashover, Derbyshire, England

Chesterfield / Ashover

1 3 2 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Child friendly ; Car advised; No pets allowed;
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

Book Book View

from £80 / night

(3) Very Good 

1 / 6

1 The Rumblings - Barlow cottage sleeps 4

Chesterfield / Barlow

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Car advised; 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

Book Book View

from £55 / night

1 / 53

Manor House - Chesterfield cottage sleeps 10

Derbyshire / Chesterfield

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Child friendly ; No pets allowed; 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

Enquire Enquire View

from £123 / night

1 / 6

THE RUMBLINGS 1 - Chesterfield house sleeps 4

Derbyshire / Chesterfield

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Not suitable for children; No pets allowed;
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

Enquire Enquire View

from £45 / night

1 / 16

PK936 Cottage in Rowsley - Stonedge house sleeps 7

Chesterfield / Stonedge

4 7 7 nights min stay

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Child friendly ; Car advised; 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

Enquire Enquire View

from £93 / night

1 / 5

Gardener's Cottage - Clay Cross cottage sleeps 3

Chesterfield / Clay Cross

2 3 7 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min stay
Key info: 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

Enquire Enquire View

from £47 / night

1 / 7

The Old Blacksmiths - Clay Cross cottage sleeps 4

Chesterfield / Clay Cross

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: 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

Enquire Enquire View

from £42 / night

1 / 16

PK880 Cottage in Chesterfield - Ashover house sleeps 10

Chesterfield / Ashover

4 10 7 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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

Enquire Enquire View

from £192 / night

1 / 19

Chesterfield / Clay Cross

2 3 3 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min stay
Key info: Suitable for children age 5+; Pet friendly;
 …see more

from £47 / night

£323 - £588 / week

Enquire Enquire View

from £47 / night

1 / 6

The Byre - Clay Cross cottage sleeps 2

Chesterfield / Clay Cross

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: 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

Enquire Enquire View

from £36 / night

1 / 14

Wood view lodge - Cutthorpe apartment sleeps 4

Chesterfield / Cutthorpe

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: 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

Book Book View

from £75 / night

1 / 12

PK762 Cottage in Chesterfield - New Tupton house sleeps 4

Chesterfield / New Tupton

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Child friendly ; Car advised; 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

Enquire Enquire View

from £54 / night

1 / 9

14137 - Castle Cottage - Palterton house sleeps 7

Chesterfield / Palterton

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: 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

Enquire Enquire View

from £40 / night

1 / 9

20 Holland Road - Chesterfield house sleeps 7

Derbyshire / Chesterfield

3 7 3 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min stay
Key info: 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

Book Book View

from £124 / night

1 / 11

William Street North - Chesterfield house sleeps 13

Derbyshire / Chesterfield

5 13 3 nights min stay

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min stay
Key info: 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

Book Book View

from £124 / night

1 / 10

Spinney - Stonedge cottage sleeps 2

Chesterfield / Stonedge

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Not suitable for children; No pets allowed; 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

Enquire Enquire View

from £43 / night

Top Destination reviews

The Old Byre
LOVELY HOME

We have really enjoyed our stay at The Old Byre,it is a beautiful property with everything there that you could possibly need.We met the owners on arrival as they live next door but,after that we were left to our own devices which was great,we we … see more
Old Robin Hood Grade II listed
Great weekend away for 14

14 of us stayed at the cottage for the bank holiday weekend and had an absolutely amazing time! We were attending a wedding in Baslow about 10 minutes down the road on Saturday and Sunday so most of our time was spent there, however in the time w … see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page