Search Holiday Rentals in Chesterfield

Search over 1 million properties and 550 airlines worldwide

Save 10% or more on select stays with Expedia Rewards

Most hotels are fully refundable. Because flexibility matters.

Top Holiday Rentals in Chesterfield

Chesterfield Serviced Apartments

Chesterfield Serviced Apartments

2 out of 5
5 Market Street, Chesterfield, England
Situated in Chesterfield, this apartment building is 2.9 mi (4.6 km) from Grassmoor Country Park and within 6 miles (10 km) of Hardwick Hall and Chesterfield ...
1.7/5 (6 reviews)
"Don’t really have a nice thing to say about it. Took 40 mins and asking for directions from a local pub to find the place as the directions they gave were not helpful. We got there and the tv was hanging off it’s wall stands. Walls were damp. Freezing cold as the radiators weren’t good and didn’t ..."

Reviewed on 1 Jan 2020

Chesterfield Serviced Apartments
PETS WELCOME! Character cottage. Secluded courtyard garden.

PETS WELCOME! Character cottage. Secluded courtyard garden.

46 Church Street, Clowne, Chesterfield, ENG
This family-friendly Chesterfield cottage is located in the mountains, 3 mi (4.8 km) from The Harley Gallery, and within 6 mi (10 km) of Creswell Crags and Rother ...
5/5 Exceptional! (3 reviews)
Wow! 5*
"Beautiful cottage close to town and up the road where we were attending a wedding. Would 100% stay again if we are that way. Bottle of wine and other treats left for us to enjoy too. 5*"

Reviewed on 11 Nov 2021

PETS WELCOME! Character cottage. Secluded courtyard garden.
Boythorpe House

Boythorpe House

3.5 out of 5
103 Bacons Lane, Chesterfield, England
Situated in Chesterfield, this holiday home is within 1 mile (2 km) of Chesterfield Market and Mecca Bingo. Peak District National Park and Barrow Hill Roundhouse ...
Boythorpe House
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Rural location on the edge of a small Derbyshire village of Holymoorside

Rural location on the edge of a small Derbyshire village of Holymoorside

Loads Road, Millclose cottage, Holymoorside, Chesterfield, ENG
This family-friendly Chesterfield cottage is located on the riverfront, 2.5 mi (4 km) from Peak District National Park, and within 6 mi (10 km) of Chesterfield ...
4.9/5 Exceptional! (59 reviews)
Lovely cottage near the Peak District
"Beautiful cottage in a lovely setting, the location just outside the peak district boundary meant it was easy to drive to all locations within the area but also close to shops and a supermarket when needed. The owners were really helpful."

Reviewed on 15 Nov 2021

Rural location on the edge of a small Derbyshire village of Holymoorside
Ernest's Retreat Glamping Site

Ernest's Retreat Glamping Site

2 out of 5
Highashes Lane Ashover, Chesterfield, England
Situated in Chesterfield, this campsite is within 6 miles (10 km) of Mecca Bingo, Lumsdale Valley and Chesterfield Market. Chesterfield Museum & Art Gallery ...
Ernest's Retreat Glamping Site
Bolsover House

Bolsover House

3.5 out of 5
50 Houfton Road, Chesterfield, England
Situated in Chesterfield, this holiday home is 0.9 mi (1.4 km) from Bolsover Castle and 2.8 mi (4.4 km) from Sutton Scarsdale Hall. Poolsbrook Country Park and ...
Bolsover House
Netherfield Cottage

Netherfield Cottage

3.5 out of 5
6 Hardstoft Road Pilsley, Chesterfield, England
Situated in Chesterfield, this golf cottage is 1.9 mi (3.1 km) from Hardwick Hall-Derbyshire Country Park and 2.7 mi (4.4 km) from Hardwick Hall. Grassmoor Country ...
Netherfield Cottage
Compton Lodge

Compton Lodge

3 out of 5
17 Compton St, Chesterfield, England
Situated in the historical district, this holiday home is 10.1 mi (16.2 km) from Beauchief Abbey and 12 mi (19.3 km) from Chatsworth House. Sheffield Hallam ...
Compton Lodge
The Olde Coach House

The Olde Coach House

3.5 out of 5
13 Gladstone Road, Chesterfield, England
Situated in Chesterfield, this cottage is within a 15-minute walk of Mecca Bingo and Chesterfield Market. Barrow Hill Roundhouse Railway Centre is 2.9 mi (4.7 ...
The Olde Coach House
Woodthorpe Cruck Cottage

Woodthorpe Cruck Cottage

3.5 out of 5
Woodthorpe Cruck Cottage Ashover Road, Old Tupton, Chesterfield, England
Situated in Chesterfield, this golf cottage is 2.9 mi (4.7 km) from Grassmoor Country Park and within 6 miles (10 km) of Chesterfield Market and Chesterfield ...
Woodthorpe Cruck Cottage
BUDGET ACCOMMODATION MINS FROM JUNCTION 30M1 FREE PARKING.  Chesterfield

BUDGET ACCOMMODATION MINS FROM JUNCTION 30M1 FREE PARKING. Chesterfield

21 Hollin Hill Rd, Chesterfield, ENG
The price is £160 per night from 5 Dec to 5 Dec
Situated in Chesterfield, this holiday home is 2.6 mi (4.1 km) from The Harley Gallery and within 6 miles (10 km) of Creswell Crags and Bolsover Castle. Renishaw ...
4.8/5 Exceptional! (4 reviews)
Great
"Great place to stay in the Worksop Clowne area"

Reviewed on 26 Jul 2019

BUDGET ACCOMMODATION MINS FROM JUNCTION 30M1 FREE PARKING. Chesterfield
Beautifully Renovated 1880s Coach House With Hot Tub, on Edge of Peak District

Beautifully Renovated 1880s Coach House With Hot Tub, on Edge of Peak District

2.5 out of 5
13 Gladstone Road, Chesterfield, England
Situated in the suburbs, this holiday home is within a 15-minute walk of Mecca Bingo and Chesterfield Market. Barrow Hill Roundhouse Railway Centre is 3 mi (4.8 ...
Beautifully Renovated 1880s Coach House With Hot Tub, on Edge of Peak District
Dryden House Summary:

Dryden House Summary:

Dryden Avenue 7, Chesterfield, ENG
Situated in Chesterfield, this holiday home is within 1 mile (2 km) of Chesterfield Market and Mecca Bingo. Peak District National Park and Sutton Scarsdale ...
Dryden House Summary:
Harvey House Summary:

Harvey House Summary:

15 Harvey Road, Chesterfield, ENG
Situated in Chesterfield, this holiday home is within 3 miles (5 km) of Chesterfield Market, Mecca Bingo and Barrow Hill Roundhouse Railway Centre. Sutton Scarsdale ...
Harvey House Summary:
Staveley House Summar

Staveley House Summar

Chesterfield Road 59, Chesterfield, ENG
Situated in Chesterfield, this holiday home is 2.2 mi (3.6 km) from Barrow Hill Roundhouse Railway Centre and within 6 miles (10 km) of Chesterfield Market and ...
2/5 (1 review)
Cleanliness poor no tv in each room as stated
"Ok for short period"

Reviewed on 25 Jun 2020

Staveley House Summar
West Lea House Summar

West Lea House Summar

18 West Lea, Chesterfield, ENG
Situated in Chesterfield, this holiday home is within 6 miles (10 km) of The Harley Gallery, Creswell Crags and Bolsover Castle. Rother Valley Country Park and ...
West Lea House Summar
Large 2-bed House Derbyshire off Chatsworth rd

Large 2-bed House Derbyshire off Chatsworth rd

3 out of 5
Chester Street, Chesterfield, England
Situated in Chesterfield, this holiday home is within a 15-minute walk of Mecca Bingo and Chesterfield Market. Peak District National Park and Barrow Hill Roundhouse ...
Large 2-bed House Derbyshire off Chatsworth rd
Beautiful 4 bed House near the Peak District

Beautiful 4 bed House near the Peak District

78 Tapton View Rd, Chesterfield, ENG
Located in the heart of Chesterfield, this golf holiday home is within 1 mile (2 km) of Mecca Bingo and Chesterfield Market. Barrow Hill Roundhouse Railway Centre ...
4.7/5 Exceptional! (3 reviews)
Convenient spot
"Very good on the whole but the property was advertised as accommodating 8 people and it only had enough table places for 4. Only 4 dinner sets too. Although there were 8 beds, two were downstairs in a room that had no curtains. Two of the curtain fittings upstairs were very loose and one set fell ..."

Reviewed on 14 Aug 2021

Beautiful 4 bed House near the Peak District
Holland House Summary

Holland House Summary

Holland Road 145, Chesterfield, ENG
Situated in Chesterfield, this holiday home is within 3 miles (5 km) of Barrow Hill Roundhouse Railway Centre, Chesterfield Market and Mecca Bingo. Peak District ...
Holland House Summary
2 bedroom accommodation in Cutthorpe

2 bedroom accommodation in Cutthorpe

Ambron House Ingmanthorpe Cutthorpe, Chesterfield, ENG
Situated in Chesterfield, this cottage is 2.9 mi (4.7 km) from Peak District National Park and within 6 miles (10 km) of Mecca Bingo and Chesterfield Market. ...
2 bedroom accommodation in Cutthorpe
Don't see what you're looking for?
See all available properties in Chesterfield
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Chesterfield you may be interested in

Ringwood Hall Hotel & Spa

Ringwood Hall Hotel & Spa

4 out of 5
Chesterfield Road, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is £85 per night from 19 Dec to 19 Dec
Ringwood Hall Hotel & Spa
Peak Edge Hotel

Peak Edge Hotel

4 out of 5
Darley Road Stone Edge, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is £162 per night from 6 Dec to 6 Dec
Peak Edge Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Holiday Apartments in Chesterfield

Search for holiday rentals in Chesterfield on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield

Frequently asked questions