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Chesterfield holiday rentals

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Best Chesterfield holiday rentals

Most recommended holiday rentals in Chesterfield

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Large 2-Bed House Derbyshire off Chatsworth rd - Chesterfield - Living room
Large 2-Bed House Derbyshire off Chatsworth rd
Chesterfield, ENG, United Kingdom
8.0Very Good(12)
Free Wi-Fi
£140+
Check availability
Thorntree Lodge - Chesterfield - Living room
Thorntree Lodge
Chesterfield, ENG, United Kingdom
9.5Wonderful(3)
Free Wi-Fi
£224+
Check availability
Middlecroft House - Chesterfield - Bedroom
Middlecroft House
Chesterfield, ENG, United Kingdom
Parking
Free Wi-Fi
£145+
Check availability
Middlecroft - Chesterfield
Middlecroft
Chesterfield, ENG, United Kingdom
8.8Very Good(51)
Parking
Free Wi-Fi
Pet-friendly
£66+
Check availability
Somersall Park Studio - Chesterfield
Somersall Park Studio
Chesterfield, ENG, United Kingdom
9.5Wonderful(258)
Parking
Free Wi-Fi
Pet-friendly
£74+
Check availability
The Loft - Chesterfield
The Loft
Chesterfield, ENG, United Kingdom
9.3Wonderful(98)
Parking
Free Wi-Fi
£67+
Check availability
Commuters Getaway - Chesterfield
Commuters Getaway
Chesterfield, ENG, United Kingdom
8.6Very Good(70)
Parking
Free Wi-Fi
Pet-friendly
£88+
Check availability
Chesterfield Serviced Apartments - Chesterfield
Chesterfield Serviced Apartments
Chesterfield, ENG, United Kingdom
4.1Mediocre(44)
Free Wi-Fi
£180+
Check availability
Chatsworth stables - Chesterfield
Chatsworth stables
Chesterfield, ENG, United Kingdom
9.2Wonderful(45)
Free Wi-Fi
Pet-friendly
£81+
Check availability
Little Manor - Chesterfield
Little Manor
Chesterfield, ENG, United Kingdom
8.5Very Good(25)
Parking
Free Wi-Fi
Pet-friendly
£91+
Check availability
One Double Room And One Spacious Attic Room In Shared House, Free Wifi, Free Parking, Amazing View - Chesterfield
One Double Room And One Spacious Attic Room In Shared House, Free Wifi, Free Parking, Amazing View
Chesterfield, ENG, United Kingdom
8.3Very Good(24)
Parking
Free Wi-Fi
£79+
Check availability
Cozy Kingsize Bedroom Shared House 3 - Chesterfield
Cozy Kingsize Bedroom Shared House 3
Chesterfield, ENG, United Kingdom
10Wonderful(1)
Parking
Free Wi-Fi
£49+
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Compton Lodge - Chesterfield
Compton Lodge
Chesterfield, ENG, United Kingdom
8.4Very Good(32)
Free Wi-Fi
£141+
Check availability
The Pottery Flat Chesterfield Three Star Gold - Chesterfield
The Pottery Flat Chesterfield Three Star Gold
Chesterfield, ENG, United Kingdom
9.3Wonderful(107)
Parking
Free Wi-Fi
Pet-friendly
£159+
Check availability
Nice Rooms in Queen House - Chesterfield
Nice Rooms in Queen House
Chesterfield, ENG, United Kingdom
9.4Wonderful(185)
£48+
Check availability
The Dance School - 1 and 2 Bedroom Apartments in the Heart of Chesterfield - Chesterfield
The Dance School - 1 and 2 Bedroom Apartments in the Heart of Chesterfield
Chesterfield, ENG, United Kingdom
9.1Wonderful(43)
Free Wi-Fi
£134+
Check availability
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Property Types

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Good to know

Low season

November

High season

December

Average price (weeknight)

£58

Average price (weekend night)

£62
Cheapest month to stay with an average 26% drop in price.
Most expensive month to stay with an average 36% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chesterfield holiday rental deals

  • Pet-friendly is the most popular holiday rental property amenity in Chesterfield
  • Holiday rentals in Chesterfield are around 65% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chesterfield.
  • The best holiday rental properties in Chesterfield are Garden Cottage - Ashover Village near Matlock (9.7, 100 reviews), The Tack Room Cottage (9.6, 22), and Kneese Loft (9.6, 94), based on ratings and reviews from real travellers.
  • If you’re looking for a cheap holiday rental in Chesterfield, you should consider visiting during the low season. The cheapest holiday homes in Chesterfield can be found in November and March.
  • The cheapest night for renting a holiday home in Chesterfield is Thursday. In contrast, the most expensive is Monday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Chesterfield for 6 days.
See more tips

FAQs when booking a holiday home in Chesterfield

  • How much is a holiday rental for a week in Chesterfield?

    The average price for a weekly Chesterfield holiday rental found by KAYAK users in the last 2 weeks is £413.

  • How much is a holiday rental for a month in Chesterfield?

    The average price for a monthly Chesterfield holiday rental found by KAYAK users in the last 2 weeks is £1,772.

  • What types of holiday rentals are available in Chesterfield?

    There are loads of different property types that you can make your holiday home in Chesterfield. You’ll find apartments, campgrounds, cottages, houses, homestays and lodges.

  • What are some of the most-loved holiday rentals available in Chesterfield?

    There are many types of properties available for Chesterfield holiday rentals. If you’re looking for something special, holiday rentals most loved by KAYAK users are Somersall Park Studio and William's Hillsborough Apartments.

  • Are there any pet-friendly holiday rentals in Chesterfield?

    There are a number of dog and pet-friendly Chesterfield holiday rentals, with around 27% allowing you to bring your pet along with you.

  • How can I find holiday rentals near me in Chesterfield?

    Take a look at our holiday rentals map to find the best holiday rental homes near you.

See more FAQs

Where to stay in Chesterfield?

Our map will help you find the perfect place to stay in Chesterfield by showing you the exact location of each holiday rental.

Everything you need to know for your stay in Chesterfield

Chesterfield holiday rental deals. Search for holiday homes, apartments, condos, cabins, cottages, villas and more in Chesterfield. Find cheap holiday homes to rent in Chesterfield. KAYAK searches hundreds of travel sites to help you find and book a holiday rental in Chesterfield that suits you best.

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