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

Exterior | Clearview, Barlow, near Chesterfield

Barlow, near Chesterfield, Derbyshire

Clearview

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.4

out of 5

7 nights

From

£929
View
Reserve today for only £25
Exterior | Oakleigh, Holymoorside

Holymoorside, Derbyshire

Oakleigh

Wifi
Car parking on site
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.6

out of 5

7 nights

From

£333
View
Reserve today for only £25
Exterior | Amber Lodge, Ashover

Ashover, Derbyshire

Amber Lodge

Wifi
Car parking on site
Detached
  • 5 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.5

out of 5

7 nights

From

£669
View
Reserve today for only £25
Entrance and small patio area  | Calf Close Barn, Ashover

Ashover, Derbyshire

Calf Close Barn

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

7 nights

From

£367
View
Reserve today for only £25
Exterior | The Stables, Northedge

Northedge, Derbyshire

The Stables

Wifi
Car parking on site
Detached
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£357
View
Reserve today for only £25
Exterior | Bathurst Cottage, Chesterfield

Chesterfield, Derbyshire

Bathurst Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.9

out of 5

7 nights

From

£543
View
Reserve today for only £25
Exterior | Barn View, Clay Cross

Clay Cross, Derbyshire

Barn View

Wifi
Car parking on site
Enclosed Garden / Patio
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.9

out of 5

7 nights

From

£483
View
Reserve today for only £25
Exterior | Green Farm Cottages - The Old Cow Shed - Green Farm Holiday Cottages, Cutthorpe, near Chesterfield

Cutthorpe, near Chesterfield, Derbyshire

Green Farm Cottages - The Old Cow Shed

Wifi
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£327
View
Reserve today for only £25
Exterior | Ramblers Retreat, Matlock

Matlock, Derbyshire

Ramblers Retreat

Hot Tub
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 3 Pets

4.5

out of 5

7 nights

From

£413
View
Reserve today for only £25
Living area | Greenwell Cottage, Chesterfield

Chesterfield, Derbyshire

Greenwell Cottage

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

5

out of 5

7 nights

From

£915
View
Reserve today for only £25
Exterior | Acorn Cottage, Ashover

Ashover, Derbyshire

Acorn Cottage

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

5

out of 5

7 nights

From

£572
View
Reserve today for only £25

Dog Friendly Cottages in Chesterfield

Exterior | The Stables, Northedge

Northedge, Derbyshire

The Stables

Wifi
Car parking on site
Detached
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£357
View
Reserve today for only £25
Exterior | Barn View, Clay Cross

Clay Cross, Derbyshire

Barn View

Wifi
Car parking on site
Enclosed Garden / Patio
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.9

out of 5

7 nights

From

£483
View
Reserve today for only £25
Exterior | Green Farm Cottages - The Old Cow Shed - Green Farm Holiday Cottages, Cutthorpe, near Chesterfield

Cutthorpe, near Chesterfield, Derbyshire

Green Farm Cottages - The Old Cow Shed

Wifi
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£327
View
Reserve today for only £25
Exterior | Ramblers Retreat, Matlock

Matlock, Derbyshire

Ramblers Retreat

Hot Tub
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 3 Pets

4.5

out of 5

7 nights

From

£413
View
Reserve today for only £25
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

7 nights

From

£427
View
Reserve today for only £25
Exterior | Acorn Cottage, Ashover

Ashover, Derbyshire

Acorn Cottage

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

5

out of 5

7 nights

From

£572
View
Reserve today for only £25
Living area | South Carolina Farm House, Matlock

Matlock, Derbyshire

South Carolina Farm House

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 3 Pets

4.7

out of 5

7 nights

From

£775
View
Reserve today for only £25
Living area | The Garden House - The Chantry, Dronfield, near Chesterfield

Dronfield, near Chesterfield, Derbyshire

The Chantry - The Garden House

Wifi
Car parking on site
Enclosed Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.7

out of 5

7 nights

From

£437
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

4.5

out of 5

7 nights

From

£825
View
Reserve today for only £99

Luxury Holiday Cottages in Chesterfield

Exterior | Clearview, Barlow, near Chesterfield

Barlow, near Chesterfield, Derbyshire

Clearview

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.4

out of 5

7 nights

From

£929
View
Reserve today for only £25
Living area | Greenwell Cottage, Chesterfield

Chesterfield, Derbyshire

Greenwell Cottage

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

5

out of 5

7 nights

From

£915
View
Reserve today for only £25
Living area | South Carolina Farm House, Matlock

Matlock, Derbyshire

South Carolina Farm House

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 3 Pets

4.7

out of 5

7 nights

From

£775
View
Reserve today for only £25
Exterior | The Willows, Teversal

Teversal, Nottinghamshire

The Willows

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

7 nights

From

£749
View
Reserve today for only £25
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

7 nights

From

£1,412
View
Reserve today for only 25%
Hot tub | Alton Hall Cottage, Alton, nr Chesterfield

Alton, nr Chesterfield, Derbyshire

Alton Hall Cottage

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

5

out of 5

7 nights

From

£1,202
View
Reserve today for only £99
Exterior | West Barn, Holymoorside, nr. Chesterfield

Holymoorside, near Chesterfield, Derbyshire

West Barn

Luxury
Wifi
Car parking on site
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

7 nights

From

£1,019
View
Stunning converted church | The Old Church, Alton, near Chesterfield

Alton, near Chesterfield, Derbyshire

The Old Church

Luxury
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 3 Bathrooms
  • 0 Pets

4.9

out of 5

7 nights

From

£473
View
Reserve today for only £25

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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