Chesterfield holiday homes

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: Discover Chesterfield's rich heritage through its stunning historic buildings and landmarks.
  • Charming town centre: Stroll through the picturesque town centre, filled with unique shops and local eateries.
  • Outdoor adventures: Enjoy various parks and green spaces ideal for family outings and relaxation.
  • Cultural experiences: Immerse yourself in local culture with museums and galleries showcasing the area's history.
  • Friendly atmosphere: Experience the warm welcome of Chesterfield's community, perfect for a budget-friendly holiday.

Top attractions in and around Chesterfield

Chesterfield offers a blend of outdoor and cultural adventures, ideal for families and those seeking a scenic retreat. Explore urban parks, historic houses, and buildings that reflect the town's rich heritage. This charming city guarantees a memorable experience with its mix of cultural attractions and natural beauty, perfect for a versatile holiday. Discover the heart of Chesterfield and enjoy its unique character on your visit.

  • Hardwick Hall: A stunning example of Elizabethan architecture, Hardwick Hall boasts magnificent rooms filled with historical artefacts and beautiful gardens. Its unique glass façade offers a glimpse into the opulence of the past, making it a perfect spot for history enthusiasts.
  • Chatsworth House: Renowned for its exquisite art collection and stunning landscape gardens, Chatsworth House is a must-visit for culture lovers. The house's grandeur and the surrounding parkland provide a captivating experience.
  • Chatsworth House Labyrinth: An enchanting garden experience, the Chatsworth House Labyrinth offers visitors a chance to explore its intricate pathways while enjoying the natural beauty and tranquillity of the surroundings.

Things to do recommended for couples

Chesterfield offers charming experiences for couples. Explore the picturesque market square, enjoy a leisurely stroll along the River Rother, or share a cosy meal at a local bistro. Don't miss the iconic Crooked Spire for a romantic photo opportunity.

Things to do recommended for families

Families will love exploring the vibrant Chesterfield Market, where local crafts and treats await. Visit the fascinating Chesterfield Museum for a dose of history, or enjoy a day at Poolsbrook Country Park, perfect for picnics and outdoor fun.

Things to do recommended for groups

Groups visiting Chesterfield can explore the famous crooked spire of St Mary and All Saints Church, enjoy a guided tour of the historic market, and sample local delicacies at the Chesterfield Market. Don't miss the stunning Chatsworth House nearby for a taste of English heritage.

*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

If you're travelling with a group, family, bringing your pets, or seeking extended stays, be sure to prioritise your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chesterfield with a group: Consider the number of bedrooms you require, as well as features like a fully equipped kitchen or an outdoor area suitable for a group gathering. Luckily, you can use filters on Vrbo to search for all these options and more.
  • Traveling to Chesterfield with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chesterfield: For many families, a trip isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that every member of your family feels at home.
  • Planning for a long term stay visiting Chesterfield: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Chesterfield

Explore Chesterfield, a vibrant city in Derbyshire perfect for outdoor adventures and serene holidays. Wander the charming town centre, appreciate the scenic beauty, and enjoy the friendly, budget-conscious atmosphere. Whether you're looking to immerse yourself in local culture or simply relax, Chesterfield offers a delightful mix of nature and urban life for a memorable holiday.

  • Sheffield: Sheffield is a vibrant city located 16km from Chesterfield, offering travellers a dynamic blend of urban life and outdoor adventure. Visitors can immerse themselves in the city's rich industrial heritage while enjoying modern recreational areas, arena entertainment, and bustling shopping centres. The city's close proximity to a renowned stadium and expansive national parks provides a perfect setting for both leisurely strolls and exhilarating explorations. Sheffield's natural scenery and lively cultural scene make it a top pick for those seeking a mix of adventure and relaxation.
  • Matlock: Matlock is a charming city situated 14km from Chesterfield, celebrated for its picturesque landscapes and thrilling outdoor pursuits. Travellers can experience the excitement of a cable car ride that offers breathtaking views of the surrounding countryside, along with exploring recreational areas and scenic gondola rides. The city's landmarks, including a notable monument and both national and state parks, provide ample opportunities for memorable adventures. Matlock is an ideal destination for those keen on exploring nature, history, and stunning vistas.
  • Bakewell: Bakewell is a delightful city located 18km from Chesterfield, perfect for those seeking an immersive outdoor and adventure experience. The area boasts extensive trail access and hiking opportunities that weave through its charming landscapes, set against the backdrop of impressive national parks and historical monuments. With its blend of natural beauty and engaging outdoor activities, Bakewell invites visitors to explore its unique rural charm and scenic allure.

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.

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

Booking with Vrbo is simple

Are you keen to cut costs on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and the type of holiday rental you prefer.

Vrbo Trips: Effortless planning

Vrbo's pioneering Trip Board offers a dedicated area to build fresh itineraries, pick up where you last stopped, or simply review and organise your plans. Any properties you've saved or booked before will now appear under Potential, Upcoming, or Current Trips. To access your Trip Boards, please visit: https://www.bookabach.co.nz/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 Bookabach 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. Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach.
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, Bookabach 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 Bookabach 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 Bookabach 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 Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.