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.

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Chesterfield

Popular Holiday Cottages in Chesterfield

View | Yew Tree Cottage, Chesterfield
Customers' Choice

Chesterfield, Derbyshire

Yew Tree Cottage

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

4.5

out of 5

7 nights

From

£455
View
Beautiful and relaxing holiday cottage | The Mill Cottage, Heath, near Chesterfield
Customers' Choice

Heath, near Chesterfield, Derbyshire

The Mill Cottage

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

4.6

out of 5

7 nights

From

£535
View
Entrance and small patio area | Calf Close Barn, Ashover
Customers' Choice

Ashover, Derbyshire

Calf Close Barn

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

4.8

out of 5

7 nights

From

£419
View
Exterior | Holly Cottage, Ashover, near Matlock.

Ashover, near Matlock., Derbyshire

Holly Cottage

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.2

out of 5

7 nights

From

£567
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

7 nights

From

£1,296
View
Living area | South Carolina Farm House, Matlock
Customers' Choice

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

£737
View
Exterior | Acorn Cottage, Ashover

Ashover, Derbyshire

Acorn Cottage

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

5

out of 5

7 nights

From

£597
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

4.7

out of 5

7 nights

From

£851
View
Living area | Smithy Apartment, Matlock

Matlock, Derbyshire

Smithy Apartment

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4

out of 5

7 nights

From

£425
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

7 nights

From

£459
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

7 nights

From

£405
View
Exterior | The Malt Shovel, Alton, near Matlock

Alton, near Matlock, Derbyshire

The Malt Shovel

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

4.8

out of 5

7 nights

From

£505
View

Dog Friendly Cottages in Chesterfield

View | Yew Tree Cottage, Chesterfield
Customers' Choice

Chesterfield, Derbyshire

Yew Tree Cottage

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

4.5

out of 5

7 nights

From

£455
View
Beautiful and relaxing holiday cottage | The Mill Cottage, Heath, near Chesterfield
Customers' Choice

Heath, near Chesterfield, Derbyshire

The Mill Cottage

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

4.6

out of 5

7 nights

From

£535
View
Exterior | Holly Cottage, Ashover, near Matlock.

Ashover, near Matlock., Derbyshire

Holly Cottage

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.2

out of 5

7 nights

From

£567
View
Living area | South Carolina Farm House, Matlock
Customers' Choice

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

£737
View
Exterior | Acorn Cottage, Ashover

Ashover, Derbyshire

Acorn Cottage

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

5

out of 5

7 nights

From

£597
View
Exterior | Meadowrise Barn, Chesterfield

Chesterfield, Derbyshire

Meadowrise Barn

  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 3 Pets

7 nights

From

£627
View
Living area | Smithy Apartment, Matlock

Matlock, Derbyshire

Smithy Apartment

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4

out of 5

7 nights

From

£425
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

7 nights

From

£459
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

7 nights

From

£405
View
Exterior | The Malt Shovel, Alton, near Matlock

Alton, near Matlock, Derbyshire

The Malt Shovel

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

4.8

out of 5

7 nights

From

£505
View
Exterior | Harris House, Inkersall, near Chesterfield

Inkersall, near Chesterfield, Derbyshire

Harris House

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.4

out of 5

7 nights

From

£455
View

Luxury Holiday Cottages in Chesterfield

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

7 nights

From

£1,296
View
Living area | South Carolina Farm House, Matlock
Customers' Choice

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

£737
View
Ridge Cottage, Chesterfield

Chesterfield, Derbyshire

Ridge Cottage

Wifi
Car parking on site
Pub within 1 mile
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

7 nights

From

£2,147
View
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

7 nights

From

£951
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

7 nights

From

£525
View
Exterior | The Pantiles, Chesterfield

Chesterfield, Derbyshire

The Pantiles

Pets stay free
Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • 12 Guests
  • 5 Bedrooms
  • 3 Bathrooms
  • 2 Pets

5

out of 5

7 nights

From

£1,266
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

7 nights

From

£1,092
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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