Chesterfield holiday rentals

We found 1,184 holiday rentals — enter your dates for availability
Select from 45 homes, 96 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:11 Dec - 18 Dec

Living area
Dining
Living area
Living area
Wonderful
(35 reviews)

Beautiful, Large Cottage, village location in The heart of the Derbyshire Dales

Matlock

9% off
AU$3,712
for 7 nights, 1 cottage
AU$530 per night
includes taxes & fees
Beautiful, Large Cottage, village location in The heart of the Derbyshire Dales
Family Room Double Bed
Property grounds
Living Room with Juliette Balcony
Exterior
Exceptional
(100 reviews)

Historic Cottage in a Traditional Mill Village

Matlock

19% off
AU$749
for 7 nights, 1 cottage
AU$107 per night
includes taxes & fees
Historic Cottage in a Traditional Mill Village
Interior
Leading up to Cosy corner cottage
Living area
Living area
Exceptional
(244 reviews)

✨ Cosy Corner Cottage – A Cosy Hideaway in the Peak District 🏡

Bakewell

23% off
AU$1,390
for 7 nights, 1 cottage
AU$199 per night
includes taxes & fees
✨ Cosy Corner Cottage – A Cosy Hideaway in the Peak District 🏡
Exterior
Room
Living area
Living area
Exceptional
(5 reviews)

Handsome house in lovely village of Rowsley, ideal as a Peak District base

Matlock

18% off
AU$2,000
for 7 nights, 1 home
AU$286 per night
includes taxes & fees
Handsome house in lovely village of Rowsley, ideal as a Peak District base
Super wood burning stove.
Afternoon Tea as photographed by some of our guests
Back yard
View from top of back garden with the Derwent valley below.
Exceptional
(6 reviews)

Detached, 6 bedroomed cottage in Matlock Bath, on the edge of the Peak District

Matlock

42% off
AU$6,697
for 7 nights, 1 cottage
AU$957 per night
includes taxes & fees
Detached, 6 bedroomed cottage in Matlock Bath, on the edge of the Peak District
The kitchen ground floor
From the driveway few steps down towards the front door.
3rd bedroom the family room 2 doubles 1 single sleeps 5
The living room
Exceptional
(42 reviews)

Good Central Based

Matlock

5% off
AU$2,806
for 7 nights, 1 home
AU$401 per night
includes taxes & fees
Good Central Based
Exterior
Property grounds
Living area
Interior
Exceptional
(51 reviews)

Beautiful 2 bedroomed stone cottage in the centre of Crich

Matlock

9% off
AU$1,545
for 7 nights, 1 cottage
AU$221 per night
includes taxes & fees
Beautiful 2 bedroomed stone cottage in the centre of Crich
Living area
Exterior
Living area
Private kitchen
Exceptional
(8 reviews)

Luxury accommodation in the old village of Aston

Sheffield

5% off
AU$1,377
for 7 nights, 1 home
AU$197 per night
includes taxes & fees
Luxury accommodation in the old village of Aston
Outside Patio Area
Longstone View Bakewell
Fully Equipped Kitchen
Living room with original Quarry Tiles
Exceptional
(51 reviews)

Bakewell Stone Cottage/Sleeps 4/Log Burning Stove/Parking /2 Bathrooms/ WiFi

Bakewell

13% off
AU$1,712
for 7 nights, 1 cottage
AU$245 per night
includes taxes & fees
Bakewell Stone Cottage/Sleeps 4/Log Burning Stove/Parking /2 Bathrooms/ WiFi
Open plan kitchen leading to dining and living area.
Jackson Tor House, 3 Holiday Lets with Top - Birds Nest, Middle - Swallow View
Open plane living area/ dining and full kitchen
Dining table extends out to double size.
Exceptional
(6 reviews)

Skylark View, Family getaway with Amazing Views

Matlock

14% off
AU$1,872
for 7 nights, 1 apartment
AU$267 per night
includes taxes & fees
Skylark View, Family getaway with Amazing Views

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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)
  • Denby Pottery (14.7 mi / 23.6 km)
  • Walesby Forest (17.5 mi / 28.2 km)
  • Dore and Totley Golf Club (6.7 mi / 10.8 km)
  • Beauchief Golf Course (7.8 mi / 12.5 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)
  • Queen's Park (0.6 mi / 0.9 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)
  • Longshaw Country Park (9.6 mi / 15.5 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?
When considering the best area to stay in Chesterfield, you'll find that the town offers several charming neighbourhoods, each with its own unique character and attractions. One popular area is the town centre, which is ideal for those who want easy access to a variety of shops, restaurants, and cultural experiences. Here, you can explore the stunning architecture of the famous Crooked Spire Church, a true icon of Chesterfield, and enjoy a leisurely stroll through the bustling market square.Another lovely neighbourhood is Hasland, which boasts a more suburban feel while still being close to the town's amenities. This area is known for its friendly community atmosphere and proximity to local parks, making it a great choice for families. Nearby, you can visit the beautiful Chesterfield Canal, great for scenic walks and spotting wildlife.For those seeking a bit of history, staying near the Old Whittington area can be quite appealing. This neighbourhood offers easy access to historical sites and is just a short distance from the stunning Bolsover Castle, where you can immerse yourself in the area's rich heritage.Chesterfield has a good selection of holiday rental properties, ranging from quaint cottages to modern apartments, suiting various preferences and budgets.
What is the most popular type of holiday rental accomodation in Chesterfield?
In Chesterfield, cottages are the most popular type of holiday rental, with around 332 available throughout the area. These charming properties are often found in picturesque neighbourhoods, providing a cosy and traditional atmosphere. Most cottages typically feature fully equipped kitchens, comfortable living areas, and outdoor spaces, allowing guests to enjoy the surrounding countryside.For those seeking a bit more space, there are approximately 112 holiday houses available, which generally offer multiple bedrooms and larger living areas, making them ideal for families or groups. Additionally, there are about 16 apartments and around 12 chalets, with amenities such as modern kitchens and convenient locations close to local attractions like the famous Chesterfield Crooked Spire and nearby parks.
Are there any family house rentals in Chesterfield?
In Chesterfield, there are numerous family-friendly house rentals available, with about 46 options throughout the area. Visitors can find properties in neighbourhoods such as Hasland and Brampton, both known for their welcoming atmospheres. Many homes in these locales boast spacious living areas, fully equipped kitchens, and outdoor spaces where children can play safely.Additionally, amenities such as Wi-Fi and laundry facilities are typically included, ensuring a comfortable stay for families. Close to these rental properties, families can explore attractions like the famous Crooked Spire of St. Mary's and the picturesque Queen's Park, which features playgrounds and beautiful walking paths.
Can I rent a holiday home with a pool or hot tub in Chesterfield?
In Chesterfield, there are several holiday homes available for rent that feature pools or hot tubs. This charming market town, located in Derbyshire, offers a variety of accommodations that cater to different preferences. Many of these properties often come with amenities such as private gardens, outdoor seating areas, and well-equipped kitchens, providing a comfortable and convenient stay.Travellers can expect to find houses with spacious living areas, ideal for families or groups, and some may even include additional features like barbecue facilities or games rooms.
Are there pet-friendly house rentals in Chesterfield?
In Chesterfield, there are numerous pet-friendly house rentals available, with around 64 options to choose from. Many of these holiday homes feature amenities such as well-equipped kitchens, spacious living areas, and private gardens, making them ideal for families or groups travelling with pets.The town is known for its rich heritage, and nearby areas like the Peak District National Park offer stunning landscapes and numerous walking trails where pets are welcome. Chesterfield itself boasts charming parks, including Queen's Park, which provides a lovely setting for leisurely strolls with your furry companions. The proximity to local shops and cafes adds to the convenience for pet owners looking to explore the area. See all pet-friendly rentals in Chesterfield.
Are there any remote work holiday rentals in Chesterfield?
In Chesterfield, there are a substantial number of remote work-friendly holiday rentals available, with around 432 options to choose from. This picturesque town, known for its historic sites and charming market square, offers a variety of accommodations suitable for those looking to blend work and leisure.Many of these properties come equipped with essential amenities for remote work, including free Wi-Fi, dedicated desks, and comfortable living spaces that allow for productivity. Guests can expect to find modern kitchens for preparing meals and cosy lounges for relaxation after work hours.Additionally, Chesterfield's proximity to attractions such as the famous Crooked Spire and the stunning Peak District National Park makes it an appealing destination for those seeking a balance between work and recreation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chesterfield?
In Chesterfield, popular rental amenities include kitchens, which allow guests to prepare their own meals, making stays more convenient and homely. Many properties also permit pets, suiting travellers who wish to bring their furry companions along. Onsite parking is another common feature, providing ease of access for those travelling by car. Additionally, accommodations often allow service animals, ensuring that guests with specific needs are well accommodated. Many rentals also boast gardens, offering a lovely outdoor space for relaxation and enjoyment.
When is the best time to visit Chesterfield for a holiday rental?
April is the most popular month to visit Chesterfield, as it marks the transition into spring, bringing with it a burst of colour and life. The peak season runs from February to April, attracting visitors eager to explore the charming market town and its surrounding countryside. During this time, outdoor activities flourish, with mild temperatures typically ranging from 5 to 15 degrees Celsius, making it comfortable for sightseeing and enjoying the fresh air.April offers a delightful atmosphere, with the famous Chesterfield Market showcasing local produce and crafts. Strolling through the market, you can experience the vibrant community spirit and perhaps even indulge in some delicious local treats. The picturesque surroundings also provide ample opportunities for leisurely walks, particularly in the nearby Peak District National Park, which is just a short drive away.For those seeking a more budget-friendly option, visiting Chesterfield in December can be a great alternative. The town takes on a magical quality during the festive season, with twinkling lights and seasonal markets, allowing you to enjoy a unique holiday experience while avoiding the peak crowds.
What are the top attractions in Chesterfield?
In Chesterfield, visitors can explore a range of attractions that showcase the town's rich history and vibrant culture. The iconic Crooked Spire of St Mary's and All Saints' Church is a must-see, with its distinctive twisted tower visible from miles around. The church is situated in the heart of the town, making it easily accessible for holidaymakers.The Chesterfield Market, one of the largest outdoor markets in the UK, is another highlight, where visitors can browse an array of local produce, crafts, and unique items. The market is surrounded by various shops and cafes, offering a lively option.For those interested in history, the Chesterfield Museum and Art Gallery provides insights into the town's heritage and features exhibitions that reflect local life. Nearby, the historic Revolution House, linked to the 1688 Glorious Revolution, offers a glimpse into the past with its period furnishings.Nature lovers can enjoy a stroll in Queen's Park, which is close to the town centre and features beautiful gardens, a boating lake, and a children's play area.
Are all fees included in the Chesterfield holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chesterfield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chesterfield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chesterfield holiday homes?
You can find great discounts on holiday homes in Chesterfield on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chesterfield holiday home booking on Stayz?
To find Chesterfield holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chesterfield?
A long-stay holiday home in Chesterfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chesterfield holiday home?
Book your Chesterfield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chesterfield?
Prices for holiday homes in Chesterfield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chesterfield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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