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 | Ramblers Retreat, Matlock

Matlock, Derbyshire

Ramblers Retreat

Hot Tub
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 3 pets allowed

4.7

out of 5

7 nights

From

£423
View
Reserve today for only £25
Freebirch Barn, Freebirch near Baslow, Bakewell

Freebirch, near Chatsworth, Bakewell, Derbyshire

Freebirch Barn

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£805
View
Entrance and small patio area  | Calf Close Barn, Ashover

Ashover, Derbyshire

Calf Close Barn

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£407
View
Open plan living space | The Barn, Holymoorside near Chesterfield

Holymoorside near Chesterfield, Derbyshire

The Barn

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 3
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£383
View
Exterior | Woodview Lodge, Cutthorpe, near Chesterfield

Cutthorpe, near Chesterfield, Derbyshire

Woodview Lodge

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£583
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
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

4.3

out of 5

7 nights

From

£457
View
Reserve today for only £25
Stunning converted church | The Old Church, Alton, near Chesterfield

Alton, near Chesterfield, Derbyshire

The Old Church

Luxury
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 3 bathrooms
  • Up to 0 pets allowed

4.9

out of 5

7 nights

From

£533
View
Reserve today for only £25
Exterior | Acorn Cottage, Ashover

Ashover, Derbyshire

Acorn Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£572
View
Reserve today for only £25
Patio | Stone Cottage, Wingerworth

Wingerworth, Derbyshire

Stone Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£443
View
Reserve today for only £25
Exterior | Priestfield Grange - Chestnut Cottage, Old Brampton, nr. Bakewell

Old Brampton, near Chesterfield, Derbyshire

Priestfield Grange - Chestnut Cottage

Car parking on site
Pub within 1 mile
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£463
View
Reserve today for only £25
Living area | Greenwell Cottage, Chesterfield

Chesterfield, Derbyshire

Greenwell Cottage

Hot Tub
Luxury
Wifi
  • Sleeps up to 8
  • 4 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£985
View

Dog Friendly Cottages in Chesterfield

Exterior | Ramblers Retreat, Matlock

Matlock, Derbyshire

Ramblers Retreat

Hot Tub
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 3 pets allowed

4.7

out of 5

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
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£583
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
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

4.3

out of 5

7 nights

From

£457
View
Reserve today for only £25
Exterior | Acorn Cottage, Ashover

Ashover, Derbyshire

Acorn Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£572
View
Reserve today for only £25
Exterior | Priestfield Grange - Chestnut Cottage, Old Brampton, nr. Bakewell

Old Brampton, near Chesterfield, Derbyshire

Priestfield Grange - Chestnut Cottage

Car parking on site
Pub within 1 mile
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£463
View
Reserve today for only £25
Exterior | The Hollies, Tansley, near Matlock

Tansley, near Matlock, Derbyshire

The Hollies

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

7 nights

From

£287
View
Exterior | Mill Farm Cottage - Kingfisher Cottage - Mill Farm Cottages, Barlow near Bakewell

Barlow near Bakewell, Derbyshire

Mill Farm Cottage - Kingfisher Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

7 nights

From

£555
View
Reserve today for only £25
Relaxing hot tub | Boundary Cottage, Old Whittington, near Chesterfield

Old Whittington, near Chesterfield, Derbyshire

Boundary Cottage

Hot Tub
Wifi
Car parking on site
  • Sleeps up to 5
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£443
View
Reserve today for only £25
Exterior | The Pantiles, Chesterfield

Chesterfield, Derbyshire

The Pantiles

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 12
  • 5 bedrooms
  • 3 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£1,434
View
Reserve today for only 25%
Exterior | The Stables, Northedge

Northedge, Derbyshire

The Stables

Wifi
Car parking on site
Detached
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

7 nights

From

£313
View

Luxury Holiday Cottages in Chesterfield

Stunning converted church | The Old Church, Alton, near Chesterfield

Alton, near Chesterfield, Derbyshire

The Old Church

Luxury
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 3 bathrooms
  • Up to 0 pets allowed

4.9

out of 5

7 nights

From

£533
View
Reserve today for only £25
Living area | Greenwell Cottage, Chesterfield

Chesterfield, Derbyshire

Greenwell Cottage

Hot Tub
Luxury
Wifi
  • Sleeps up to 8
  • 4 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£985
View
Exterior | West Barn, Holymoorside, nr. Chesterfield

Holymoorside, near Chesterfield, Derbyshire

West Barn

Luxury
Wifi
Car parking on site
  • Sleeps up to 8
  • 4 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£1,019
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
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 3 pets allowed

4.8

out of 5

7 nights

From

£779
View
Exterior | Clearview, Barlow, near Chesterfield

Barlow, near Chesterfield, Derbyshire

Clearview

Luxury
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

4.3

out of 5

7 nights

From

£749
View
Exterior | The Willows, Teversal

Teversal, Nottinghamshire

The Willows

Luxury
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£749
View
Hot tub | Alton Hall Cottage, Alton, nr Chesterfield

Alton, nr Chesterfield, Derbyshire

Alton Hall Cottage

Hot Tub
Luxury
Wifi
  • Sleeps up to 10
  • 4 bedrooms
  • 4 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£1,174
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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