Chesterfield Cottages

Experience the perfect holiday getaway in Chesterfield with cottages.com. Nestled in the heart of beautiful countryside, Chesterfield offers a unique blend of history, culture, and natural beauty.

Chesterfield

Popular Holiday Cottages in Chesterfield

Living area | Greenwell Cottage, Chesterfield

Chesterfield, Derbyshire

Greenwell Cottage

Hot Tub
Luxury
Wifi
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.9

out of 5

15 Jan•7 nights

£937
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Beautiful and relaxing holiday cottage | The Mill Cottage, Heath, near Chesterfield
Customers' Choice

Heath, near Chesterfield, Derbyshire

The Mill Cottage

Wifi
Car Parking On Site
Detached
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.7

out of 5

11 Dec•7 nights

£533
View
Exterior | Woodview Lodge, Cutthorpe, near Chesterfield
Customers' Choice

Cutthorpe, near Chesterfield, Derbyshire

Woodview Lodge

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

5

out of 5

11 Nov•7 nights

£690
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Dining room | Hillcrest, Bolsover, near Chesterfield
Customers' Choice

Bolsover, near Chesterfield, Derbyshire

Hillcrest

Hot Tub
Wifi
Car Parking On Site
  • 10 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • 0 Pets

4.2

out of 5

14 Dec•7 nights

£937
View
Exterior | Holly Cottage, Ashover, near Matlock.

Ashover, near Matlock., Derbyshire

Holly Cottage

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.1

out of 5

7 Dec•7 nights

£493
View
Exterior | Bryn TorThe Gardener’s House, Bolsover, near Chesterfield
Customers' Choice

Bolsover, near Chesterfield, Derbyshire

Bryn Tor - The Gardener’s House

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 5 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.7

out of 5

26 Nov•7 nights

£721
View
Living area | The Gatehouse - The Chantry, Dronfield, near Chesterfield

Dronfield, near Chesterfield, Derbyshire

The Chantry - The Gatehouse

Wifi
Car Parking On Site
Enclosed Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4

out of 5

8 Jan•7 nights

£443
View
Freebirch Barn, Freebirch near Baslow, Bakewell

Freebirch, near Chatsworth, Bakewell, Derbyshire

Freebirch Barn

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

5

out of 5

4 Jun•7 nights

£641
View
Exterior | Woodend Bungalow, Huthwaite, nr. Sutton-in-Ashfield

Huthwaite, near Sutton-in-Ashfield, Nottinghamshire

Woodend Bungalow

Wifi
Car Parking On Site
Enclosed Garden / Patio
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 3 Pets

4.7

out of 5

12 Nov•7 nights

£1,057
View
Exterior | West Barn, Holymoorside, nr. Chesterfield
Customers' Choice

Holymoorside, near Chesterfield, Derbyshire

West Barn

Luxury
Wifi
Car Parking On Site
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

12 Dec•7 nights

£1,092
View
Exterior | The Stables, Northedge
Customers' Choice

Northedge, Derbyshire

The Stables

Wifi
Car Parking On Site
Detached
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

5

out of 5

22 Jan•7 nights

£347
View

Dog Friendly Cottages in Chesterfield

Beautiful and relaxing holiday cottage | The Mill Cottage, Heath, near Chesterfield
Customers' Choice

Heath, near Chesterfield, Derbyshire

The Mill Cottage

Wifi
Car Parking On Site
Detached
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.7

out of 5

11 Dec•7 nights

£533
View
Exterior | Woodview Lodge, Cutthorpe, near Chesterfield
Customers' Choice

Cutthorpe, near Chesterfield, Derbyshire

Woodview Lodge

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

5

out of 5

11 Nov•7 nights

£690
View
Exterior | Meadowrise Barn, Chesterfield

Chesterfield, Derbyshire

Meadowrise Barn

Pub Within 1 Mile
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 3 Pets

9 Nov•7 nights

£580
View
Exterior | Holly Cottage, Ashover, near Matlock.

Ashover, near Matlock., Derbyshire

Holly Cottage

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.1

out of 5

7 Dec•7 nights

£493
View
Exterior | Bryn TorThe Gardener’s House, Bolsover, near Chesterfield
Customers' Choice

Bolsover, near Chesterfield, Derbyshire

Bryn Tor - The Gardener’s House

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 5 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.7

out of 5

26 Nov•7 nights

£721
View
Living area | The Gatehouse - The Chantry, Dronfield, near Chesterfield

Dronfield, near Chesterfield, Derbyshire

The Chantry - The Gatehouse

Wifi
Car Parking On Site
Enclosed Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4

out of 5

8 Jan•7 nights

£443
View
Exterior | Woodend Bungalow, Huthwaite, nr. Sutton-in-Ashfield

Huthwaite, near Sutton-in-Ashfield, Nottinghamshire

Woodend Bungalow

Wifi
Car Parking On Site
Enclosed Garden / Patio
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 3 Pets

4.7

out of 5

12 Nov•7 nights

£1,057
View
Exterior | The Stables, Northedge
Customers' Choice

Northedge, Derbyshire

The Stables

Wifi
Car Parking On Site
Detached
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

5

out of 5

22 Jan•7 nights

£347
View
Exterior | The Hollies, Tansley, near Matlock
Customers' Choice

Tansley, near Matlock, Derbyshire

The Hollies

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 1 Pet

4.9

out of 5

4 Mar•7 nights

£287
View
Living area | Smithy Apartment, Matlock

Matlock, Derbyshire

Smithy Apartment

Wifi
Car Parking On Site
Pub Within 1 Mile
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

3.5

out of 5

4 Dec•7 nights

£377
View

Luxury Holiday Cottages in Chesterfield

Living area | Greenwell Cottage, Chesterfield

Chesterfield, Derbyshire

Greenwell Cottage

Hot Tub
Luxury
Wifi
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.9

out of 5

15 Jan•7 nights

£937
View
Exterior | West Barn, Holymoorside, nr. Chesterfield
Customers' Choice

Holymoorside, near Chesterfield, Derbyshire

West Barn

Luxury
Wifi
Car Parking On Site
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

12 Dec•7 nights

£1,092
View
Hot tub | Alton Hall Cottage, Alton, nr Chesterfield
Customers' Choice

Alton, nr Chesterfield, Derbyshire

Alton Hall Cottage

Hot Tub
Luxury
Wifi
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • 0 Pets

5

out of 5

8 Jan•7 nights

£1,162
View
Ridge Cottage, Chesterfield

Chesterfield, Derbyshire

Ridge Cottage

Luxury
Wifi
Car Parking On Site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5 Jan•7 nights

£2,227
View
Living area | South Carolina Farm House, Matlock
Customers' Choice

Matlock, Derbyshire

South Carolina Farm House

Luxury
Wifi
Car Parking On Site
  • 7 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 3 Pets

4.7

out of 5

25 Jan•7 nights

£747
View
Stunning converted church | The Old Church, Alton, near Chesterfield
Customers' Choice

Alton, near Chesterfield, Derbyshire

The Old Church

Luxury
Wifi
Car Parking On Site
  • 4 Guests
  • 2 Bedrooms
  • 3 Bathrooms
  • 0 Pets

5

out of 5

22 Jan•7 nights

£503
View
Exterior | The Pantiles, Chesterfield

Chesterfield, Derbyshire

The Pantiles

Wifi
Enclosed Garden / Patio
Pub Within 1 Mile
  • 12 Guests
  • 5 Bedrooms
  • 3 Bathrooms
  • 2 Pets

5

out of 5

28 Oct•7 nights

£1,266
View
Exterior | Clearview, Barlow, near Chesterfield
Customers' Choice

Barlow, near Chesterfield, Derbyshire

Clearview

Luxury
Wifi
Car Parking On Site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.6

out of 5

12 Dec•7 nights

£907
View

See more cottages in Chesterfield

Self-Catering Holiday Cottages in Chesterfield

Our exclusive selection of Chesterfield cottages provides the ideal accommodation for a truly memorable holiday. Immerse yourself in the rich history of this charming town, known for its ancient market square and iconic crooked spire. Explore the picturesque Peak District National Park, located just a stone's throw away, and discover breathtaking landscapes, tranquil walks, and thrilling outdoor activities. Whether you're seeking a romantic getaway, a family adventure, or a peaceful retreat, our Chesterfield cottages are the perfect base for your holiday. With cottages.com, you can relax and unwind in your own private haven, surrounded by the beauty of Chesterfield. Book your holiday today and create lifelong memories in this enchanting destination. With the largest collection of holiday cottages in Derbyshire, we have the perfect home away from home for you.

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