
Holiday houses in Chesterfield
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Quick stats about holiday rentals in Chesterfield

Total holiday rentals
Explore 130 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $42 AUD per night before taxes and fees

Verified guest reviews
Over 8,120 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
120 of Chesterfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterfield rentals

4.8 Average rating
Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated holiday rentals in Chesterfield
Guests agree: these stays are highly rated for location, cleanliness and more.

Chatsworth Cottage
Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

Roundhouse View
Modern and comfortable 2-bedroom bungalow in a quiet area of Chesterfield. Ideal for professionals, relocations and short stays. Sleeps 3-4 with a double and flexible twin setup. Includes superfast WiFi, fully equipped kitchen, washing machine, free parking and a private enclosed garden. Well located for the M1, town centre and the Peak District. Dog-friendly on request. Discounts for longer stays. Easy self check-in and reliable host support. Ideal for quiet stays, fast access and easy parking

The Hideaway
Surround yourself with style in this standout space. Modern recently refurbished basement apartment with secure drive. It comprises of 1 bedroom with king size bed with Premier Inn mattress. It has a kitchen/lounge with pull out sofa bed that sleeps 2. The kitchen is equipped with microwave, fridge, air fryer, kettle, toaster and all utensils. Includes all bedding and towels. Shower room. 10 min walk to the chesterfield canal. Shops, pubs and restaurants are all within walking distance.

Cottage by the Park Chesterfield - Peak district
Our COTTAGE is situated with a PARK on our doorstep and 15 min drive to Baslow in the PEAK DISTRICT . Also within walking distance to Chesterfield town center and Chatsworth road. Only a 15 min walk to bars, restaurants, coffee shops, and local boutique shops on Chatsworth Road. It is a short drive to Chatsworth house, Bakewell, Matlock and many of the delightful areas in the Peak district. Our home is cozy and welcoming! We hope you will choose us for your next visit to the area.

Bright - 2 Bedroomed House in Derbyshire
Your family will be close to everything when you stay at this centrally located town house within walking distance from Chesterfield's iconic market town. This 2 bedroomed modern home has everything you need and is the perfect base for visiting all the local attractions Derbyshire has to offer. Right on the edge of the Peak District it boasts a 20 minute drive to Chatsworth House and many more. Along with all the wonderful bars, restaurants, gift & coffee shops all within walking distance.

Cosy studio apartment close to Peak District
Cosy,private ,self contained upstairs studio with own entrance , double bed with en suite, dual ring halogen hob ,combination microwave and oven , television with free sat ,free wifi ,integrated fridge freezer ,breakfast bar and stools . Comfy chairs to relax! On the main bus route into Chesterfield and the Peak District ,10 mins to Chatsworth,20 mins to Bakewell and lots of walks in the area. Many bars ,coffee shops and restaurants within walking distance . We look forward to meeting you.

Charming 18th century stone cottage
Tucked away in a peaceful corner of Newbold Village, within its own private courtyard, Carpenters Mews is a beautifully restored circa-1800 cottage. Full of character and charm, it has been thoughtfully furnished throughout. Whether you’re visiting for business, leisure, or a countryside getaway to the nearby stunning Peak District, this delightful two-bedroom home is a perfect base. It is close to all local amenities, providing everything you need for an enjoyable and comfortable stay.

The Long Hall 2 bed ground floor annexed apartment
Long Hall has been lovingly converted into a 6-person, ground floor, annexed apartment, within a quiet housing estate, a short distance from the Peak District. Two large double bedrooms, with rainfall shower en-suites, and a large open-plan living area dining and kitchen area and a large, shared enclosed patio and garden area Long Hall suits leisure and tourist staycations, as well as trade or professional workers, who wish for a home from home. SKY Sports and Movies included

Spire View | Chesterfield 2 Bedroom Apartment
Relax in style at Spire View, a beautifully renovated first-floor apartment in the heart of Chesterfield. Bright, spacious, and full of character, it offers two double bedrooms, modern comforts, kitchen and bathroom, as well as lovely views of the town’s iconic crooked spire. Perfect for couples, professionals, or small groups exploring the Peak District or working locally. Just a short walk to the train station (10 min) and town centre (5 min). Paid parking nearby from £3.80/24h

Charming grade II listed cottage with hot tub
Chander Hill Cottage is a stylish 3-bedroom barn conversion nestled above the village of Holymoorside, on the edge of the Peak District. This cosy cottage is a perfect base for exploring the countryside, with numerous walks from the door and two pubs just a mile away in the village. Relax in our hot tub with stunning views or warm up by the wood burning stove after a winter walk. The enclosed cottage garden has a patio where you can enjoy a BBQ in the summer. Dogs welcome!

2 Bed Lovely apartment close to City Center & Rail
This 2-bed Apartment is located close to Chesterfield City Center & Chesterfield Rail Station. Its in a peaceful and secure neighborhood close to Chesterfield College and Tapton Golf Course. This house is ideal for visitors to the Peak who equally want to close to town life - shops and restaurants, cinema, clubs etc. Bedrooms can be configured to have 4 separate beds given advanced notice. Ideal for families & contractor workers. You have the entire Apartment to yourself.

Crossfield Coach House
This spacious upstairs annex sleeps two, and is located ten minutes from the M1. The old coach house is attached to the family home, but with its own entrance, and behind electric gates it is completely private. The space has a separate shower room, fully fitted kitchen, a lounge and separate bedroom. The annex has access to an outdoor patio with seating and the use of a barbeque. The coach house is within walking distance of, shops pubs and restaurants.
Popular amenities for Chesterfield holiday rentals
Stay near Chesterfield's top sights
Other great holiday rentals in Chesterfield

A cosy 2 bedroom family friendly living space

Home in Chesterfield

Blissful Barry’s

9NQS A comfortable home in Chesterfield

The Farmhouse at Cow Close Farm

Town Centre Modern Apartment

Peak District Escape | Business & Leisure Stay

The Old School House
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $152 AUD | $153 AUD | $163 AUD | $171 AUD | $170 AUD | $175 AUD | $153 AUD | $166 AUD | $145 AUD | $156 AUD | $150 AUD | $153 AUD |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
Frequently Asked Questions
What are the best places to stay in Chesterfield?
Look for accommodations around the town center, Hasland, or the Brampton area, which have convenient access to shops and local attractions. Neighborhoods near parks may appeal to those seeking a quieter stay.
What are the best things to do in Chesterfield with kids?
Queen’s Park has playgrounds and open spaces, while local museums and swimming pools provide indoor options. Family-friendly events and seasonal activities add variety throughout the year.
What are some of the best things to do in Chesterfield?
Explore outdoor markets, visit the Church of St Mary and All Saints with its iconic spire, and relax in Queen’s Park. The town has museums, cozy cafés, and easy access to countryside trails.
How is the weather in Chesterfield?
Chesterfield experiences cool winters around 35–44°F (2–7°C), and milder summers averaging 54–71°F (12–22°C). Rain is common year-round, so a waterproof jacket is useful most seasons.
When is the best time to visit Chesterfield?
Late spring and summer are often recommended for milder temperatures and longer daylight hours. Autumn brings colorful foliage, while winter is cooler and tends to be wetter.
What are the best places to visit in Chesterfield?
Enjoy the unique Church of St Mary and All Saints, stroll through Queen’s Park, or discover local history at Chesterfield Museum. The outdoor market brings a lively atmosphere on market days.
What are some hiking trails in Chesterfield?
Explore scenic paths in Queen's Park, wander the countryside around the Peak District, or stroll along canal towpaths. These trails provide a blend of nature, parkland, and gentle walking routes.
What are some family activities we can do in Chesterfield?
Explore the play areas in Queen’s Park, visit local museums, or enjoy leisure centers with swimming and sports facilities. Family walks and outdoor events are frequently suggested on weekends.
What are some of the best day trip ideas from Chesterfield?
Visit the countryside around the Peak District, explore historic stately homes, or tour nearby market towns. Nature reserves and heritage attractions are frequently suggested for day excursions.
Are there any pet friendly accommodations available in Chesterfield?
Pet-friendly stays are available in Chesterfield, particularly around residential neighborhoods and near green spaces. Many hosts welcome pets and provide guidance on local dog walks.
What are some local tips for visiting Chesterfield?
Arriving early for market days is frequently suggested, as you’ll find fresh produce and handmade goods. Carrying an umbrella is helpful, and locals often stroll Queen’s Park for relaxation.
What is Chesterfield known for?
Chesterfield is known for its historic crooked church spire, vibrant outdoor markets, and access to the Peak District. The town blends local heritage with countryside appeal.
What are the best hidden gems to explore in Chesterfield?
Wander lesser-known paths around the Chesterfield Canal, discover small galleries, or enjoy tucked-away cafés in Brampton. These spots provide quieter alternatives to main attractions.
What are the best foods to try in Chesterfield?
Chesterfield has traditional pies, locally baked bread, and hearty pub fare. Afternoon tea is frequently suggested, with sweet treats and locally made cakes featured in cafés.
What should I bring for a trip to Chesterfield?
Pack waterproof clothing and comfortable walking shoes, as rain can happen in any season. Layers are useful for changing temperatures, and a camera may help capture historic architecture and scenery.
What is the nightlife in Chesterfield like?
Chesterfield has a mix of traditional pubs, relaxed bars, and venues with live music. The town center and Brampton area are known for welcoming atmospheres and community events.
What are the most popular events or festivals in Chesterfield?
The Chesterfield Market Festival and annual medieval-themed events are often recommended. Seasonal celebrations, including local fairs and arts festivals, mark highlights on the town’s calendar.
Are there family friendly vacation rentals in Chesterfield?
Many rentals in Chesterfield have family-friendly amenities and are located near parks, shopping, or leisure centers. Options often include homes or apartments with spacious layouts.
Destinations to explore
- Peak District National Park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- Heaton Park
- Donington Park Circuit
- The Quays
- Didsbury Village
- Lincoln Castle
- AO Arena
- Harewood House
- Tatton Park
- Bowlers Exhibition Centre
- University of Manchester
- Yorkshire Wildlife Park
- Wythenshawe Park
- Bramham Park
- Manchester Central Convention Complex
- The Piece Hall
- Temple Newsam Park
- Belvoir Castle
- Mam Tor
- Yorkshire Sculpture Park
- Loughborough University





