Holiday rentals 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 £23 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    120 of Chesterfield holiday rentals include wifi 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.

1 of 1 pages1 / 1
Guest favourite
The exterior of the brick house is showcased, featuring a charming door with a small balcony above. Large windows allow natural light in, while the well-maintained driveway provides ample space for parking. A clear blue sky enhances the welcoming appearance of the property.
Home
4.97 out of 5 average rating, 63 reviews

Home in Chesterfield

Welcome to our quirky upside down renovation, Casa Vault. A unique but cosy bolt hole, close to the centre of Chesterfield and perfect for visiting the Peak District. Ideally located near the infamous Brampton Mile, which is a walkable mile of pubs, restaurants and shops. You can enjoy easy access to Chatsworth and Bakewell from this centrally located place which was formally a cash register repair shop. You have full access to the whole property which has two bedrooms and two extra bed settees.

Top guest favourite
The Tower emerges from a lush green landscape, surrounded by tall trees and manicured grass. The building's robust concrete structure is accented by its original window designs, reflecting the natural beauty of the outdoors in a tranquil setting.
Tower
5 out of 5 average rating, 239 reviews

The Tower

The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

Guest favourite
A modern, light-filled living area features a gray sectional sofa adorned with colorful, geometric pillows. A simple wall-mounted shelf is visible on the left, and a front door, partially open, allows natural light to enter the space.
Townhouse
4.91 out of 5 average rating, 186 reviews

Cheerful 2- Bedroomed Home in Chesterfield.

This beautiful town house is located right on the edge of the Peak District and within walking distance to 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. The locations boasts a 20 min drive to the well loved Peak District. Along with all the wonderful bars, restaurants, gift & coffee shops just a short walk away. Chesterfield's Golf course is just 15min drive away.

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
4.87 out of 5 average rating, 114 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.

Top guest favourite
Home
4.95 out of 5 average rating, 37 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.

Superhost
A light-filled living area features a comfortable sectional sofa in soft gray, complemented by decorative pillows. A dark coffee table occupies the center space, while large glass doors open to a private outdoor seating area, enhancing the connection to nature.
Home
4.85 out of 5 average rating, 41 reviews

Blissful Barry’s

A quiet detached house on a cul-de-sac on the edge of the Peak District. A short stroll from pubs and an India restaurant. 10 mins walk to the chesterfield canal, only 10 mins into the town centre by car with the famous crooked spire. The house has 2 double bedrooms both with a double bed and a single bedroom with a full sized raised single bed. Matlock and Bakewell is about a 30 minute drive and both lovely places to visit. Beds are made up for arrival with linen and towels included

Superhost
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.
Apartment
4.95 out of 5 average rating, 19 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

Guest favourite
A comfortable living area is furnished with a gray sectional sofa and two leather armchairs. A glass coffee table is positioned centrally, and a wooden cabinet stands against the wall, adding storage space. Double doors lead to the outside, allowing natural light to enter.
Home
4.96 out of 5 average rating, 350 reviews

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

Top guest favourite
Home
5 out of 5 average rating, 29 reviews

The Cow Shed at Dale House Farm

A perfect base for walking, visiting stately homes including Chatsworth and Haddon Hall, cycling or just simply relax and enjoy the endless unspoilt countryside. A short 10 minute drive to the Market Town of Chesterfield, with many bars, cafes, shops & cinema. Or 15 minute drive to Bakewell and other Peak District attractions. The Cow Shed is a luxury property, recently restored and converted to a very high standard which is available as a 1 bedroom property, with hot tub.

Top guest favourite
The exterior of a modern two-story annex is presented, displaying a mix of dark wood and white walls. Large windows allow natural light, while a covered entrance is visible. Neatly arranged planters line the base, contributing to a tidy appearance.
Flat
5 out of 5 average rating, 63 reviews

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.

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.
Apartment
4.83 out of 5 average rating, 144 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
4.98 out of 5 average rating, 272 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.

Popular amenities for Chesterfield holiday rentals

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price£82£83£88£75£76£76£83£90£78£84£81£83
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°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.