Destinations and properties:
Dates and flexibility:
Select dates
Party makeup:
Guests

Filters

Price range

Based on a 7 night stay

£420
£1,500+

Reset

Property makeup
Dogs allowed
Minimum star grading
Collections
Property type
Recently added
Chesterfield • Dates • Guests

Chesterfield cottages

10 properties found

Chesterfield, Peak District

Southwood Chase

1044

Our grading

7 nights

£2,482 - £4,970

View
These properties are nearby.

Barlow, Derbyshire

Barlow Brook Cottage

211

Our grading

7 nights

£784 - £892

View

Baslow (5.3 mls E), Peak District

Ash Tree Cottage

211

Our grading

7 nights

£536 - £889

View

Barlow, Peak District

Mulberry Cottage - Peak

422

Our grading

7 nights

£550 - £989

View

Barlow, Peak District

The Little Trout

4211

Our grading

7 nights

£451 - £790

View

Keep me updated with new properties, holiday ideas and special offers!

Please enter a valid email address.

At holidaycottages.co.uk, part of The Travel Chapter Group, your privacy is paramount to us. You can read in our privacy statement how we safeguard your data. You can opt out at any time.

Holymoorside (1.6 mls W), Peak District

Besom Cottage

422

Our grading

7 nights

£582 - £1,120

View

Holmesfield, Peak District

Hills Cottage

422

Our grading

7 nights

£425 - £788

View

Baslow (5.3 mls E), Peak District

Aero Cottage

4212

Our grading

7 nights

£487 - £876

View

Barlow, Peak District

Wellside Cottage

4212

Our grading

7 nights

£443 - £764

View

Tansley (4.6mls E), Peak District

Tollgate Cottage

742

Our grading

7 nights

£949 - £1,621

View

Self-catering holiday cottages in Chesterfield

Stay at one of our self-catering holiday cottages in Chesterfield, Derbyshire. Combining Derbyshire and the beautiful Peak District, Chesterfield is the best of both worlds. History buffs will enjoy finding out the secrets of Chesterfield, such as how the Crooked Spire got its twist or experiencing the romantic atmosphere of Bolsover Castle. Outdoor activities, heritage sites and various eateries make this the perfect market town to visit. Yet there’s more to this Derbyshire market town at the edge of the Peak District National Park than its twisted spire. With an interesting history, Chesterfield is known for being the site of some important historical events like the plot to overthrow King James II/VII, and the town’s large role in the Industrial Revolution. Also, the Victorian-era ‘father of railways’, George Stephenson lived in Chesterfield. Handily, the town is also home to a weekly market, as well as a wide choice of shops, banks, supermarkets and evening entertainment. Chesterfield is within good driving distance to Matlock and Belper for shopping alternatives and days out. In Matlock Bath, you’ll find the glorious Heights of Abraham and in Belper, interesting historical evidence of its own status as one of the most active centres of the fledgling Industrial Revolution.

During your getaway to this beautiful corner of Derbyshire, unwind on long walks and visit nearby towns, villages and attractions before retiring to your own cosy cottage in Chesterfield to relax. Seek out a cottage with a wood burner for toasty evenings snuggled up together. If you’d like more inspiration, take a look through our full collection of cottages across Derbyshire and the Peak District. Begin planning your next break to this scenic part of England by finding your ideal holiday cottage in our Chesterfield collection.