Chesterfield holiday lettings

We found 963 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 49 homes, 103 cottages and other holiday rentals in Chesterfield to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

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The friendly area of Chesterfield awaits your stay

Come and experience Chesterfield and its churches, culture and theatre scene. Well known for its bars, parks and restaurants, this welcoming city won't disappoint. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Chesterfield

Are you hoping to find things to do during your stay? Venture out of your holiday home and check out everything that makes Chesterfield a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Gulliver's Valley (9 mi / 14.5 km)
  • Gulliver's Kingdom (10 mi / 16.2 km)
  • Tropical Butterfly House, Wildlife and Falconry Centre (12.3 mi / 19.7 km)
  • Walesby Forest (17.5 mi / 28.2 km)
  • Dore and Totley Golf Club (6.7 mi / 10.8 km)
  • Virgin Balloon Flights (10.3 mi / 16.7 km)

Exploring the natural features in Chesterfield

Whether you're an outdoor enthusiast or just want to take in the scenery, Chesterfield is a great place to get outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Peak District National Park (18.4 mi / 29.7 km)
  • Chatsworth House Labyrinth (7.8 mi / 12.5 km)
  • Rother Valley Country Park (8.4 mi / 13.5 km)
  • Creswell Crags (9.6 mi / 15.4 km)
  • Heights of Abraham (9.8 mi / 15.7 km)
  • Endcliffe Park (9.9 mi / 15.9 km)

How to get to and around Chesterfield

The nearest airport is in Doncaster (DSA-Sheffield), located 24.3 mi (39.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Nottingham (NQT), which is 26 mi (41.9 km) away.

If you prefer train travel, the main station is Chesterfield Station.

Frequently asked questions

What is the best area to stay in Chesterfield when booking a holiday rental?

Ashover is one of the more popular locations to find a Vrbo holiday home in Chesterfield. Choose from our comfy stays and then prepare to discover this destination like a local.

What is the most popular type of holiday rental accommodation in Chesterfield?

Based on our research, cottages are the most desirable type of holiday property in Chesterfield. But having said that, everyone's idea of the perfect trip can differ. Vrbo has holiday homes of all shapes and sizes, and we'll help you to find the perfect fit for you.

How much does it cost to rent a holiday rental in Chesterfield?

Season, length of stay and property type are some of the things that can determine the price of a holiday home. Simply add your travel dates to find your ideal fit. From comfy cabins to expansive villas, all Vrbo holiday rentals provide amazing value.

How much does it cost to rent a beach house in Chesterfield?

When you travel and the size and style of the property will influence how much you'll pay for your beachside holiday rental. Click on your Chesterfield travel dates to view your available options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the amenities and features you want in your beach house.

Are there pet-friendly holiday rentals in Chesterfield?

With 70 holiday rentals that allow pets, your furry best friend can join in on your Chesterfield holiday. Use the filter tool to search our pet-friendly holiday rentals and find a stay that'll set tails wagging on Vrbo.

What are popular rental amenities in Chesterfield?

The most popular rental amenities people prefer in Chesterfield are a fireplace, a firepit and a barbecue grill. Whether you're on the road with family, pals or even pets, Vrbo holiday homes provide the best amenities for fun and relaxation with the people you cherish the most.

Are there large group holiday rentals in Chesterfield?

Chesterfield has eight holiday rentals that can host 10 or more guests. These properties come with plenty of space to share good times with your favourite people.

Are there holiday rentals in Chesterfield that welcome kids?

With 70 family-friendly holiday properties available in Chesterfield, now is a fantastic time to introduce the kiddos to the wonders of travel. Simply check our "Properties good for families" filter to locate stays that feature amenities perfect for families on the move, like full kitchens, pools, bunk beds and entertainment areas.

What are the top attractions for families in Chesterfield?

Keeping the kiddos entertained during your holiday in Chesterfield is a breeze with these fabulous family-friendly attractions:

  • Bolsover Castle
  • Barrow Hill Roundhouse Railway Centre
  • Chesterfield Museum & Art Gallery

Are there one-bedroom holiday rentals in Chesterfield?

Yes, Chesterfield has eight one-bedroom rentals available. Usually located in popular areas thanks to their compact size, a one-bedroom property is perfect if you're travelling with your partner or a pal. And with home comforts like air conditioning and more privacy than a standard hotel, you'll be able to kick back while discovering this exciting destination.

Can I find two-bedroom holiday rentals in Chesterfield?

Gather your besties and relax in total privacy and comfort in one of the 24 two-bedroom holiday properties Chesterfield has to offer.

Are there holiday rentals with WiFi in Chesterfield?

Chesterfield has eight holiday rentals with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to sending emails, these Vrbo homes make it a cinch to go online.