Holiday houses in Chesterfield

Find and book unique accommodation on Airbnb

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 $52 NZD 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, Wi-Fi 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.

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Top Guest favourite
Cottage in Chesterfield
4.93 out of 5 average rating, 346 reviews

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.

Superhost
A spacious garden area is visible, featuring a variety of colorful flowers in pots, including bright yellow and pink blooms. A well-maintained lawn extends into the distance, accompanied by tree line and greenery. A soft play structure and garden shed are also included in the scene.
Home in Wingerworth
4.87 out of 5 average rating, 325 reviews

Oakdale - Our Quest retreat

Idyllically situated at the entrance to Hardwick Wood, Wingerworth, 2 miles from Chesterfield and all amenities, yet totally secluded. Close to Chatsworth & Peak District. Fully fitted kitchen all appliances including tumble drier & dishwasher. Underfloor zoned central heating. Log burner. Fully fitted bathroom with bath and shower. Separate shower/wc. Fully fitted bedrooms with ample wardrobes and drawers ideally suited to a family of 4. Sleeps 4 in one double and 1 set of bunks, cot available

Superhost
A bedroom is featured with a spacious bed dressed in floral bedding. A wooden wardrobe with mirrors stands beside the bed. A bedside lamp provides soft illumination, while neatly folded towels are placed at the foot of the bed, offering a sense of comfort and convenience.
Apartment in Chesterfield
4.86 out of 5 average rating, 104 reviews

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.

Guest favourite
A charming two-story cottage is presented with a welcoming façade featuring pale pink and cream walls. A quiet street is visible alongside, with a parking space indicated. Lush trees line the road, enhancing the serene environment of the neighborhood.
Townhouse in Chesterfield
4.86 out of 5 average rating, 118 reviews

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.

Guest favourite
An inviting living space is featured, showcasing a modern dining table and chairs alongside a vibrant red sideboard. A cozy armchair and a striped lounge chair add comfort, while softly illuminated pendant lights enhance the room's ambiance. Natural light filters through a window adorned with gray curtains.
Home in Chesterfield
4.91 out of 5 average rating, 116 reviews

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.

Top Guest favourite
A spacious studio is seen, featuring a wooden double bed and a breakfast bar with stools. Comfy chairs are positioned near a large television. Soft carpeted flooring complements the pastel-colored walls, and kitchen appliances are visible in the background, providing functional living space.
Apartment in Chesterfield
4.96 out of 5 average rating, 295 reviews

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.

Top Guest favourite
Home in Chesterfield
4.96 out of 5 average rating, 47 reviews

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.

Guest favourite
A light-filled living area features large arched windows that allow natural light to illuminate the space. A cozy sofa is paired with a sleek dining table set for four and complemented by modern seating. Decorative plants add a fresh touch to the inviting ambiance.
Condo in Chesterfield
4.95 out of 5 average rating, 21 reviews

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

Top Guest favourite
Barn in Holymoorside
4.99 out of 5 average rating, 202 reviews

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!

Superhost
The living area features a comfortable gray sofa, accompanied by decorative cushions. A light wooden bookshelf holds various books, while a dining table adorned with a vase of roses occupies the foreground. The space is filled with natural light from nearby windows.
Condo in Chesterfield
4.82 out of 5 average rating, 148 reviews

The Corner House A-2 Bedroom Town Centre Apartment

A stylish ground-floor apartment in a beautifully converted 1800s home, recently refurbished to a high standard and exclusively used for Airbnb guests. The property features two double bedrooms, a full bathroom plus a separate toilet, and a fully equipped open-plan kitchen/diner with a sofa bed - perfect for relaxing stays. Within walking distance of Chesterfield town centre and train station, with allocated parking for one car.

Top Guest favourite
A modern two-story home features a clean white exterior with large windows and a circular accent window. A wooden fence offers privacy to the front yard, which displays a paved pathway leading to the entrance. The sky is partly cloudy, creating a serene backdrop.
Home in Chesterfield
4.98 out of 5 average rating, 282 reviews

'Rose House' Modern 3 Bedroom Detached House

Located a mile from Chesterfield town centre. The property consists of a large open plan lounge/kitchen, 2 double bedrooms and 1 single room with bunk beds. The garden is south facing and there is private parking. There are a range of bars, cafe's, restaurants and local amenities just a short walk from the property. Chatsworth House, Haddon Hall and Peak District are 15 minutes drive away.

Guest favourite
The stone facade of the barn conversion is complemented by a charming archway entrance. Lush green plants are positioned around the door, enhancing the inviting appearance. A cobbled pathway leads towards the entrance, framed by carefully landscaped gardens and a clear blue sky overhead.
Cottage in Barlow
4.86 out of 5 average rating, 302 reviews

Old Barn Conversion close to the Peak District

This beautiful detached barn conversion has been charmingly renovated, retaining and working with many original features where possible. Tastefully furnished to a very good standard throughout, the open-plan living space has a small/compact kitchen area with a combi/microwave oven and hob. Its stunning beamed vaulted ceiling creates a warm and cosy social environment.

Popular amenities for Chesterfield holiday rentals

When is the best time to visit Chesterfield?

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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.