Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A bright studio area features a double bed with soft linens and decorative pillows. A small dining table is set for two, accompanied by a bottle of sparkling wine and glasses. Natural light floods through glass doors leading to an outdoor patio.
Guest suite in New Tupton
4.87 out of 5 average rating, 348 reviews

Studio Annexe on the Edge of the Peak District

A bright and airy ground floor annexe, used solely for guests. With its own entrance, a comfortable double bed, fully equipped kitchen and outdoor patio area, you are guaranteed a relaxing and private stay. Nestled away in the village of Tupton on the edge of the Peak District, we hope that you can find a place to relax, eat and explore. If you're with us for work, moving house or to see family, then we have everything you need from pots and pans to a washing machine as well as a space to park.

Guest favorite
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 in Derbyshire
4.93 out of 5 average rating, 146 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.

Top guest favorite
A cozy sitting area features a blue armchair with decorative pillow. A wooden mantel surrounds a small fireplace, flanked by two lamps providing soft illumination. Artwork adorns the walls, and a vintage trunk adds character to the space.
Cottage in Holymoorside
4.98 out of 5 average rating, 305 reviews

Wasp Nest Cottage, Peak District

Sitting on the edge of the Peak District, a stone’s throw from open fields, woodland and moors - sits a 19th Century cosy mill worker’s cottage. Two pubs and a shop are within easy walking distance and Chatsworth House is a beautiful 7 mile wander over the hill. Marvel at the lovely centuries old tree slice, coffee table and huge slice of elm breakfast bar, enjoy chopping boards, pottery and soft furnishings from the local artisans - just some of the magic the Peak District has to offer.

Guest favorite
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 Derbyshire
4.86 out of 5 average rating, 101 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 favorite
The room features two beds covered with yellow checkered bedspreads, complemented by blue towels at the foot of each. A small side table holds a chair and decor. Light enters through a nearby glass door, adding a bright touch to the cozy space.
Guest suite in Wingerworth
4.94 out of 5 average rating, 300 reviews

The Garden Room

The Annexe is self contained in the garden of our home in Wingerworth. Private entrance through small conservatory . Shower room , fridge, kettle, toaster , microwave. Cereals, bread, butter and preserves provided. Close to countryside and Peak District National Park . On drive parking. Bus stops nearby to Chesterfield and Derby with links by bus/train from Chesterfield Rail Station. Good local walks and Chatsworth Estate 20 minutes drive. Excellent Pub/Restaurant 5 minutes walk away.

Top guest favorite
A ground floor entrance is framed by a brick exterior. Two white chairs and a small table are positioned on a stone patio, inviting relaxation. A glass sliding door offers a view into the studio, with a landscaped area visible nearby.
Condo in Derbyshire
4.99 out of 5 average rating, 133 reviews

Chesterfield -Peak District-Chatsworth-EV Charger

Enjoy our ground floor studio, private entrance, bathroom, kitchenette with fridge freezer, microwave, double bed, wall-mounted TV. PAYG EV Charger - Ideal for business travellers and couples seeking a relaxing break. Located on a quiet, tree-lined avenue. Minutes from Chatsworth Road's bars and restaurants. Close to the Peak District, Chatsworth House, Buxton, Bakewell, and Matlock, guest access via a coded key lock. Nestled near the Hipper Valley bike trail for a peaceful retreat.

Guest favorite
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 in Chesterfield
4.96 out of 5 average rating, 331 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 favorite
The exterior of the barn conversion is shown, featuring rustic stone walls and a slate roof. An expansive gravel driveway leads to the entrance, with serene countryside visible in the background, highlighting the tranquil setting.
Condo in Holymoorside
5 out of 5 average rating, 151 reviews

Self-Catering, Log Burner, Cosy, Peak District

Welcome to Leveret! Our cosy retreat in the heart of the picturesque Peak District. Lovingly designed to provide you with the perfect blend of comfort and rustic charm! Unwind by the crackling warmth of the log burner, while relaxing on the comfortable modern furnishings! Leveret features a well-appointed king-size bedroom, fully equipped kitchen complete with modern appliances, and bathroom with bath and shower over. Private outdoor space & BBQ area in peaceful surroundings.

Top guest favorite
The exterior of a stone cottage is displayed against a clear blue sky. Large windows allow light to illuminate the façade, and a set of stone steps leads up to the entrance. Nearby trees provide a natural backdrop, enhancing the overall rustic charm.
Barn in Holymoorside
4.98 out of 5 average rating, 128 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!

Top guest favorite
A wooden lodge is illuminated by warm light in the evening dusk, surrounded by a wooden fence. Softly glowing string lights outline the perimeter, while purple flowers are visibly present in the foreground, adding a pop of color to the serene scene.
Farm stay in Derbyshire
4.96 out of 5 average rating, 287 reviews

Woolley Lodge Farm Retreat

A brand new fully furnished wooden lodge situated within the grounds of a working farm, with views across open countryside. The cabin has been furnished to a high standard and includes a double bedroom with double bed. The kitchen has a full size fridge with small freezer, full size oven and a microwave. It has a small bathroom with a full size corner shower. It has its own entrance, parking and a beautiful decked area and fire pit outside

Guest favorite
A brick garage accompanied by a paved driveway is visible. The garage door is closed, and a green recycling bin is positioned against the wall. A pet dog stands on the lower left side of the image, while trees are seen in the background.
Apartment in Hollingwood
4.87 out of 5 average rating, 178 reviews

The Loft

Immaculate Twin Loft Room with en-suite shower. Room accessed by the key in a Keysafe adjacent to the private door. Car parking for 1 vehicle available. 5 minute walk to Ringwood Hall, Canal, 3 takeaways and the Hollingwood Public House. 5 minute drive to M1 junction29a. Room has free Wifi, tea/coffee making facilities, television, microwave, fridge, clothes rail and 2 chest of drawers. Towels and bedding provided.

Top guest favorite
The exterior of the building showcases a traditional stone structure, featuring a vibrant blue door and several windows. A small garden area with gravel and low plants is visible, creating a quaint and inviting entrance alongside a simple table.
Guesthouse in Derbyshire
4.97 out of 5 average rating, 237 reviews

The Annexe - Belle Vue House

The Annexe to Belle Vue House was built for Servants to the main house in 1823. The grade 2 listed building commands an elevated position overlooking Matlock Bath. The property has been lovingly updated to keep period features while providing modern living. The property is accessible via a flight of stone stairs from the lower drive way. Due to the period nature and historic listing road side parking is necessary.

Popular amenities for Chesterfield vacation rentals

Frequently Asked Questions

  • Are there house rentals with a dedicated workspace in Chesterfield?

    Yes! Work meets play with ease at over 30 house rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Chesterfield?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with a kitchen, over 50 homes with wifi, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly house rentals in Chesterfield?

    Four-legged friends are welcome in Chesterfield. Choose from more than 20 house rentals for guests traveling with pets.

  • Are there family-friendly house rentals in Chesterfield?

    Chesterfield has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Chesterfield have a kitchen?

    Absolutely! We offer over 50 house rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Chesterfield?

    Experience the best of Chesterfield with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Chesterfield have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Chesterfield?

    Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 180 vacation rentals in Chesterfield, and over 180 vacation rentals in Brimington.

Quick stats about vacation rentals in Chesterfield

  • Total vacation rentals

    Explore 100 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at R347 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 6,960 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Chesterfield vacation 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!

  1. Airbnb
  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield