Chesterfield holiday homes

We found 1,178 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
NZ$4,688
for 7 nights, 1 cottage
NZ$670 per night
includes taxes & fees
Beautiful, Large Cottage, village location in The heart of the Derbyshire Dales
Living Room with Juliette Balcony
Property grounds
Exterior
Dining Room
Exceptional
(100 reviews)

Historic Cottage in a Traditional Mill Village

Matlock

19% off
NZ$941
for 7 nights, 1 cottage
NZ$134 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
NZ$1,723
for 7 nights, 1 cottage
NZ$246 per night
includes taxes & fees
✨ Cosy Corner Cottage – A Cosy Hideaway in the Peak District 🏡
Living area
Room
Living area
Exterior
Exceptional
(5 reviews)

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

Matlock

18% off
NZ$2,481
for 7 nights, 1 home
NZ$354 per night
includes taxes & fees
Handsome house in lovely village of Rowsley, ideal as a Peak District base
Kitchen with Belfast sink, double oven & hob, Microwave oven etc.
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
NZ$8,408
for 7 nights, 1 cottage
NZ$1,201 per night
includes taxes & fees
Detached, 6 bedroomed cottage in Matlock Bath, on the edge of the Peak District
Patio garden
From the driveway few steps down towards the front door.
The living room
3rd bedroom the family room 2 doubles 1 single sleeps 5
Exceptional
(42 reviews)

Good Central Based

Matlock

5% off
NZ$3,476
for 7 nights, 1 home
NZ$497 per night
includes taxes & fees
Good Central Based
Exterior
Property grounds
Interior
Living area
Exceptional
(51 reviews)

Beautiful 2 bedroomed stone cottage in the centre of Crich

Matlock

9% off
NZ$1,916
for 7 nights, 1 cottage
NZ$274 per night
includes taxes & fees
Beautiful 2 bedroomed stone cottage in the centre of Crich
Private kitchen
Exterior
Living area
Living area
Exceptional
(8 reviews)

Luxury accommodation in the old village of Aston

Sheffield

5% off
NZ$1,706
for 7 nights, 1 home
NZ$244 per night
includes taxes & fees
Luxury accommodation in the old village of Aston
Outside Patio Area
Longstone View Bakewell
Double Bedroom With Ensuite
Living room with original Quarry Tiles
Exceptional
(51 reviews)

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

Bakewell

13% off
NZ$2,121
for 7 nights, 1 cottage
NZ$303 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
King size bed with full wardrobe and leading to private en-suite with full bath.
Open plane living area/ dining and full kitchen
Exceptional
(6 reviews)

Skylark View, Family getaway with Amazing Views

Matlock

14% off
NZ$2,264
for 7 nights, 1 apartment
NZ$323 per night
includes taxes & fees
Skylark View, Family getaway with Amazing Views

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • 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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Chesterfield holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Chesterfield to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas