Chesterfield holiday rentals

We found 1,138 holiday rentals — enter your dates for availability
Select from 44 homes, 99 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.

Holiday rentals with weekly discounts – Chesterfield

Showing deals for:30 Oct - 6 Nov

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Why visit Chesterfield

  • Historic Architecture: Admire Chesterfield’s heritage through its iconic buildings and charming historic houses.
  • Picturesque Parks: Enjoy scenic walks and leisure in the city’s delightful urban parks and well-maintained public spaces.
  • Cultural Experiences: Immerse yourself in the vibrant town centre with local eateries and friendly locals.
  • Family-Friendly Attractions: Explore a variety of activities and sights suitable for visitors of all ages.
  • Budget-Friendly Getaways: Discover a range of comfortable stay options that ensure a relaxing and culturally enriching visit.

Popular types of accommodation in Chesterfield

Planning a getaway to Chesterfield, England? This charming town offers a variety of holiday rentals, including delightful cottages, modern apartments, and private holiday homes, all equipped with essential amenities like central heating and laundry facilities. Immerse yourself in local attractions such as the iconic Crooked Spire, vibrant markets, and stunning parks. Enjoy a memorable stay in Chesterfield, where comfort and convenience await you.

  • Cottages: Enjoy a cosy stay in traditional countryside cottages, the most sought-after choice in Chesterfield.
  • Apartments: Select modern apartments offering comfort and convenience, ranking second in popularity.
  • Private Holiday Homes: Experience a home-away-from-home in private holiday homes, a preferred option for many.
  • House Boats: Consider unique house boats, providing an unconventional yet charming retreat.
  • Bed And Breakfast: Delight in the warm hospitality of bed and breakfast accommodations, a well-loved choice.**

Top attractions in and around Chesterfield

Chesterfield, England, is a charming city perfect for outdoor enthusiasts and culture seekers alike. Discover its beautiful urban parks, explore historic houses and buildings, and enjoy family-friendly experiences throughout the area. With a rich heritage and picturesque scenery, Chesterfield offers a delightful blend of adventure and relaxation, making it an ideal destination for all types of travellers looking to immerse themselves in local culture and nature.

  • Hardwick Hall: A historic building located within Chesterfield, offering a deep dive into local cultural heritage with its grand architecture and artistic displays.
  • Chatsworth House: A historic residence 13km away, celebrated for its refined cultural ambience and stately gardens that reflect the region’s rich history.
  • Queen's Park: A vibrant urban park in Chesterfield, perfect for family outings and leisurely strolls in a lively city setting.

Things to do recommended for couples

Chesterfield offers delightful experiences for couples, such as a leisurely walk through the charming Queen's Park or enjoying a romantic meal at a local bistro. Don't miss the iconic crooked spire of St Mary’s Church, perfect for a picturesque photo together.

Things to do recommended for families

Families will love exploring the fascinating Chesterfield Museum, where children can discover local history, or enjoying a fun day at the nearby Tapton Park, featuring playgrounds and beautiful walking trails. Don't miss the iconic crooked spire of St Mary and All Saints Church for a memorable family photo.

Things to do recommended for groups

Groups visiting Chesterfield can enjoy a guided tour of the famous Crooked Spire, explore the bustling Market Square, and indulge in local delicacies at the Chesterfield Market. Don't miss a leisurely stroll along the scenic Chesterfield Canal for a taste of the area's natural beauty.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chesterfield

Whether you're travelling as a group, with your family, bringing your pets along, or planning an extended stay, be sure to apply the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Chesterfield with a group: Consider how many bedrooms you'll require, and take into account additional amenities like a fully equipped kitchen or an outdoor area for a group gathering. Fortunately, you can utilise filters on Stayz to search for all these features and more.
  • Traveling to Chesterfield with young kids: Travelling with young children can pose certain challenges. It’s essential to prioritise their comfort and safety, alongside suitable amenities like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Chesterfield: For some, a family holiday isn’t complete without their four-legged companion. If that describes you, explore Stayz properties that welcome pets. Most pet-friendly accommodations provide feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Chesterfield: If you are seeking holiday lets with special offers for stays of a month or more, you have come to the right place. With the appropriate filter, you can effortlessly discover and save on monthly rentals. You might also consider including a parking space, a well-equipped kitchen or a private swimming pool in your search.

Where to stay near Chesterfield

Chesterfield offers a charming blend of outdoor adventures and cultural delights. Explore the town centre with its vibrant atmosphere, friendly locals, and accessible central location. The city's rich history is complemented by scenic walks and inviting public spaces. Whether you’re admiring the architecture or enjoying local eateries, Chesterfield provides a budget-friendly, family-friendly experience perfect for a relaxing yet culturally enriching getaway.

  • Sheffield: Sheffield lies a mere 16km from Chesterfield, offering a vibrant blend of urban energy and natural splendour. This city is renowned for its thriving outdoor scene and adventurous spirit, where visitors can enjoy a mix of recreational areas, arena entertainment, and bustling shopping centres. Notable nearby attractions include a grand stadium and expansive national parks, providing an ideal setting for those seeking both cultural experiences and scenic escapes.
  • Matlock: Only 14km from Chesterfield, Matlock is celebrated for its picturesque landscapes and dynamic outdoor adventures. The city invites travellers to explore its recreational areas via a charming cable car and gondola, offering breathtaking views of the surrounding national parks and monuments. Matlock’s blend of natural beauty and historic landmarks makes it a compelling destination for those in search of both tranquillity and excitement.
  • Bakewell: Situated 18km away from Chesterfield, Bakewell is a delightful city that captivates visitors with its outdoor allure and scenic vistas. Ideal for those who appreciate adventurous pursuits, Bakewell offers access to serene recreational areas, well-marked trails and invigorating hiking paths. Its proximity to expansive national parks and notable monuments ensures that every visit is enriched by the natural and cultural heritage of the region.

Best time to go to Chesterfield

If you're planning a trip to Chesterfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January38.3°F (3.5°C)Light RainMostly CloudyAverageSlightly Low
February39.4°F (4.1°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
March42.3°F (5.7°C)No Rain (Dry)Mostly CloudyAverageAverage
April46.2°F (7.9°C)No Rain (Dry)Mostly CloudySlightly HighAverage
May51.8°F (11.0°C)Light RainMostly CloudyAverageAverage
June57.2°F (14.0°C)Light RainMostly CloudyAverageAverage
July60.8°F (16.0°C)Light RainMostly CloudySlightly HighSlightly High
August60.3°F (15.7°C)Light RainMostly CloudyAverageSlightly High
September56.5°F (13.6°C)No Rain (Dry)Mostly CloudySlightly HighAverage
October50.7°F (10.4°C)Light RainMostly CloudySlightly LowAverage
November44.1°F (6.7°C)Light RainMostly CloudySlightly LowSlightly Low
December40.1°F (4.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Stayz is simple

Are you hoping to make savings on your next holiday? Being flexible with your travel dates can often lead to better prices, as they tend to fluctuate. Additionally, opting for a longer stay can result in considerable discounts. To discover a Stayz property that suits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board provides an area where you can initiate new journeys, resume existing plans, or review and arrange your reservations. Properties you have either saved or booked are now categorised into Potential, Upcoming, or Current Trips. To discover Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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)
  • Virgin Balloon Flights (10.3 mi / 16.7 km)
  • Denby Pottery (14.7 mi / 23.6 km)
  • Wheelgate Park (17.2 mi / 27.7 km)
  • Walesby Forest (17.5 mi / 28.2 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)
  • Hall Leys Park (8.7 mi / 14 km)
  • Creswell Crags (9.6 mi / 15.4 km)
  • Heights of Abraham Cable Car Station (9.7 mi / 15.6 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 home?
Ashover is one of the more popular locations to find a Stayz 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 home 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. Stayz 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 home 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 Stayz holiday homes 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 home. Click on your Chesterfield travel dates to view your available options on Stayz. 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 homes in Chesterfield?
With 70 holiday homes that allow pets, your furry best friend can join in on your Chesterfield holiday. Use the filter tool to search our pet-friendly holiday homes and find a stay that'll set tails wagging on Stayz.
What are popular home amenities in Chesterfield?
The most popular home 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, Stayz holiday homes provide the best amenities for fun and relaxation with the people you cherish the most.
Are there large group holiday homes in Chesterfield?
Chesterfield has eight holiday homes 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 homes 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 homes in Chesterfield?
Yes, Chesterfield has eight one-bedroom homes 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 homes 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 homes with WiFi in Chesterfield?
Chesterfield has eight holiday homes 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 Stayz homes make it a cinch to go online.
How old do you have to be to rent a holiday home in Chesterfield?
You'll have to check with the Chesterfield holiday property you're considering on Stayz as the minimum age differs. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Chesterfield for?
The amount of time you can rent a Chesterfield holiday home for varies depending on the property. Just put in your preferred travel dates to see available options offering extended stays. They have all the things you need to make your extended getaway more comfortable and convenient, such as kitchens and laundries. Some Stayz holiday homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.