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 | 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
Setting | Mill Close Cottage, Chesterfield
Customers' Choice

Chesterfield, Derbyshire

Mill Close Cottage

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

4.9

out of 5

7 nights

From

£651
View
Patio | Perkins Cottage, Woolley Moor, near Alfreton
Customers' Choice

Woolley Moor, near Alfreton, Derbyshire

Perkins Cottage

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

5

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 | Bathurst Cottage, Chesterfield
Customers' Choice

Chesterfield, Derbyshire

Bathurst Cottage

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

5

out of 5

7 nights

From

£505
View
Exterior | Priestfield Grange - Chestnut Cottage, Old Brampton, nr. Bakewell
Customers' Choice

Old Brampton, near Chesterfield, Derbyshire

Priestfield Grange - Chestnut Cottage

Pets stay free
Car parking on site
Pub within 1 mile
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.7

out of 5

7 nights

From

£345
View
Patio | Stone Cottage, Wingerworth
Customers' Choice

Wingerworth, Derbyshire

Stone Cottage

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

4.9

out of 5

7 nights

From

£345
View

Dog friendly cottages in Chesterfield

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
Setting | Mill Close Cottage, Chesterfield
Customers' Choice

Chesterfield, Derbyshire

Mill Close Cottage

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

4.9

out of 5

7 nights

From

£651
View
Patio | Perkins Cottage, Woolley Moor, near Alfreton
Customers' Choice

Woolley Moor, near Alfreton, Derbyshire

Perkins Cottage

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

5

out of 5

7 nights

From

£737
View
Exterior | Meadowrise Barn, Chesterfield

Chesterfield, Derbyshire

Meadowrise Barn

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

7 nights

From

£627
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 | Priestfield Grange - Chestnut Cottage, Old Brampton, nr. Bakewell
Customers' Choice

Old Brampton, near Chesterfield, Derbyshire

Priestfield Grange - Chestnut Cottage

Pets stay free
Car parking on site
Pub within 1 mile
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.7

out of 5

7 nights

From

£345
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
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.4

out of 5

7 nights

From

£439
View

Chesterfield cottages with hot tubs

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
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

£1,166
View
Exterior | Ramblers Retreat, Matlock
Customers' Choice

Matlock, Derbyshire

Ramblers Retreat

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

4.9

out of 5

7 nights

From

£405
View
Dining room | Hillcrest, Bolsover, near Chesterfield
Customers' Choice

Bolsover, near Chesterfield, Derbyshire

Hillcrest

Hot Tub
Wifi
Car parking on site
  • 10 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • 0 Pets

4.7

out of 5

7 nights

From

£1,041
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

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