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 | 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
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

£493
View
Reserve today for only £25
Living room with wood burning stove | Lings Farm Cottage, Temple Normanton, near Chesterfield

Temple Normanton, near Chesterfield, Derbyshire

Lings Farm Cottage

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

£337
View
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
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
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

7 nights

From

£457
View
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

4.8

out of 5

7 nights

From

£785
View
Beautiful and relaxing holiday cottage | The Mill Cottage, Heath, near Chesterfield

Heath, near Chesterfield, Derbyshire

The Mill Cottage

Wifi
Car parking on site
Detached
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.6

out of 5

7 nights

From

£537
View
Exterior | The Bobbin, Kelstedge, near Matlock

Kelstedge, near Matlock, Derbyshire

The Bobbin

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

4.8

out of 5

7 nights

From

£427
View
Living room | Plum Tree House, Sheffield

Sheffield, West Yorkshire

Plum Tree House

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

4.5

out of 5

7 nights

From

£959
View

Dog Friendly Cottages in Chesterfield

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
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

£493
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
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

7 nights

From

£457
View
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

4.8

out of 5

7 nights

From

£785
View
Beautiful and relaxing holiday cottage | The Mill Cottage, Heath, near Chesterfield

Heath, near Chesterfield, Derbyshire

The Mill Cottage

Wifi
Car parking on site
Detached
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.6

out of 5

7 nights

From

£537
View
Exterior | The Bobbin, Kelstedge, near Matlock

Kelstedge, near Matlock, Derbyshire

The Bobbin

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

4.8

out of 5

7 nights

From

£427
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

7 nights

From

£423
View
Reserve today for only £25
Exterior | Woodview Lodge, Cutthorpe, near Chesterfield

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

7 nights

From

£583
View
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 | 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

Luxury Holiday Cottages in Chesterfield

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
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

4.8

out of 5

7 nights

From

£785
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

7 nights

From

£1,412
View
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

£1,142
View
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

£935
View
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

£919
View
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
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

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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