Holiday cottages in Chesterfield

The Derbyshire market town of Chesterfield is a short journey south of Sheffield, nestled beside the Peak District National Park. Our holiday cottages in Chesterfield allow you to explore this historic town at your own pace on your Derbyshire getaway. Read on to find out more!

St Mary and All Saints Church in Chesterfield, Derbyshire, England

Popular cottages in Chesterfield

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 room | Red Robin Cottage, New Tupton, near Chesterfield

New Tupton, near Chesterfield, Derbyshire

Red Robin Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£735
View
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 | Harris House, Inkersall, near Chesterfield

Inkersall, near Chesterfield, Derbyshire

Harris House

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.7

out of 5

7 nights

From

£453
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 room | Plum Tree House, Sheffield

Sheffield, Yorkshire

Plum Tree House

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.5

out of 5

7 nights

From

£959
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
  • 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

Dog friendly cottages in Chesterfield

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 room | Red Robin Cottage, New Tupton, near Chesterfield

New Tupton, near Chesterfield, Derbyshire

Red Robin Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£735
View
Exterior | Harris House, Inkersall, near Chesterfield

Inkersall, near Chesterfield, Derbyshire

Harris House

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.7

out of 5

7 nights

From

£453
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
Exterior | Holly Cottage, Handley, near Matlock

Handley, near Matlock, Derbyshire

Holly Cottage

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

7 nights

From

£413
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
  • 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

Chesterfield cottages with hot tubs

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
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 | 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
Dining room | Hillcrest, Bolsover, near Chesterfield

Bolsover, near Chesterfield, Derbyshire

Hillcrest

Hot Tub
Wifi
Car parking on site
  • Sleeps up to 10
  • 5 bedrooms
  • 4 bathrooms
  • Up to 0 pets allowed

4.5

out of 5

7 nights

From

£1,124
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
  • Sleeps up to 10
  • 4 bedrooms
  • 4 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£1,174
View

Things to do on your holiday in Chesterfield

Discover the town's historic landmarks

The historic Derbyshire market town is home to several iconic landmarks that showcase its rich heritage. The most famous is undoubtedly the Crooked Spire of the Church of St Mary and All Saints, with its unique twisted spire. Visitors can climb the Grade I-listed church tower for panoramic views of Chesterfield and the surrounding countryside. Just a short drive from Chesterfield, you can visit popular historic attractions like the Elizabethan Hardwick Hall, the 17th-century Baroque-style Chatsworth House and the medieval Bolsover Castle, all of which offer fascinating insights into the area's past.

Soak up the lively market atmosphere

To this day, Chesterfield retains a vibrant market town charm, with its independent shops, historic architecture and strong sense of community spirit. The inviting streets are begging to be explored, lined with charming boutiques, quaint cafes and cosy eateries. The historic open-air market, still held several days a week, offers opportunities to buy local goods, including fresh produce, crafts and antiques. Pick up something tasty to cook up in one of our Chesterfield holiday lodges or cottages, or pack yourself a picnic for long walks in the nearby Peak District.

Explore the Peak District National Park

Chesterfield is located close to the eastern edge of the Peak District, offering fantastic opportunities for walking, cycling and wildlife watching. The Peak District's rolling hills, dramatic valleys and rugged moorlands are just a short drive away, as are pretty towns and villages like Bakewell and Matlock Bath. The town is a great jumping off point for exploring the Derwent Valley, with its scenic woodland walks, popular fishing spots along the River Derwent and the UNESCO World Heritage Site of the Derwent Valley Mills. For a romantic weekend away, check out our Peak District hot tub breaks, or if you're after somewhere you can bring your canine companion, discover our dog-friendly holidays in the Peak District.

Linacre Reservoirs in Chesterfield, Derbyshire, England

Explore

A family walking in the forest

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