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 | 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

4.7

out of 5

7 nights

From

£1,362
View
Exterior | Green Farm Cottages - The Old Cow Shed - Green Farm Holiday Cottages, Cutthorpe, near Chesterfield
Customers' Choice

Cutthorpe, near Chesterfield, Derbyshire

Green Farm Cottages - The Old Cow Shed

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

4.9

out of 5

7 nights

From

£349
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
Exterior | Barn View, Clay Cross
Customers' Choice

Clay Cross, Derbyshire

Barn View

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

4.9

out of 5

7 nights

From

£485
View
Living area | South Carolina Farm House, Matlock
Customers' Choice

Matlock, Derbyshire

South Carolina Farm House

Luxury
Wifi
Car parking on site
  • 7 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 3 Pets

4.7

out of 5

7 nights

From

£741
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

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

4.7

out of 5

7 nights

From

£1,362
View
Exterior | Green Farm Cottages - The Old Cow Shed - Green Farm Holiday Cottages, Cutthorpe, near Chesterfield
Customers' Choice

Cutthorpe, near Chesterfield, Derbyshire

Green Farm Cottages - The Old Cow Shed

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

4.9

out of 5

7 nights

From

£349
View
Exterior | Barn View, Clay Cross
Customers' Choice

Clay Cross, Derbyshire

Barn View

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

4.9

out of 5

7 nights

From

£485
View
Living area | South Carolina Farm House, Matlock
Customers' Choice

Matlock, Derbyshire

South Carolina Farm House

Luxury
Wifi
Car parking on site
  • 7 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 3 Pets

4.7

out of 5

7 nights

From

£741
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
Lovely semi-detached holiday home in a picturesque rural area | Boundary Cottage, Old Whittington, near Chesterfield
Customers' Choice

Old Whittington, near Chesterfield, Derbyshire

Boundary Cottage

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

4.6

out of 5

7 nights

From

£445
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

5

out of 5

7 nights

From

£505
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
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

4.1

out of 5

7 nights

From

£1,086
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

4.8

out of 5

7 nights

From

£415
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

£1,162
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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