Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Top guest favorite
The living room features a cozy arrangement with a soft beige sofa and armchair, adorned with floral cushions. A low coffee table sits in front of a fireplace, while patterned curtains frame a bright window. A small TV is mounted on the wall above the fireplace.
Cottage in Chesterfield
4.93 out of 5 average rating, 310 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 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, 356 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.

Superhost
A well-lit bedroom features a spacious bed with softly patterned pillows and a light blanket. A full-length mirror reflects the serene space, which is enhanced by green accent walls and framed animal artwork. Natural light filters through the slatted blinds, creating a welcoming atmosphere.
Home in Derbyshire
4.89 out of 5 average rating, 9 reviews

Modern 3 bed home, Chesterfield

Modern 3 bed home in a central part of Chesterfield, within walking distance of the town centre. Downstairs there is a spacious living, dining area with tv, comfy sofa and dining table. Fully equipped breakfast kitchen with washing machine, dryer, dishwasher and table & chairs. Upstairs there are 2 double bedrooms - 1 with ensuite and a single bedroom. Family bathroom with shower over bath. Enclosed rear garden with lovely decking area and access to parking space at the back of the property.

Guest favorite
An open-plan living area is presented, featuring a cozy leather sofa and a stylish glass coffee table atop a circular rug with muted colors. Modern kitchen appliances are visible, alongside wooden shelves and decorative plants, enhancing the welcoming ambience.
Condo in Derbyshire
5 out of 5 average rating, 14 reviews

The Old Dance Studio

Welcome to our newly renovated apartment in the centre of Chesterfield, where you will be able to relax in style. Modern but full of character, the Old Dance Studio is a bright and spacious 1 bedroom ground floor flat with an open plan living space, kitchen, bathroom and access to a courtyard. Great for anyone commuting or working in the area or visiting the Peak District with a short walk to the train station and town centre. Paid parking from £3.80/24h and on street parking available nearby.

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
4.94 out of 5 average rating, 156 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 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
4.87 out of 5 average rating, 104 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
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, 285 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 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, 307 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.

Guest favorite
Home in Derbyshire
4.85 out of 5 average rating, 20 reviews

Beautiful 4 bed at gateway to the Peak District

Spacious 4 bedroom, 2.5 bathroom home at the gateway to the Peak District. Ideal for group stays, and countryside escapes. 3 min walk to Dunston Hall Wedding Venue & Garden Centre. Close to Chatsworth, Bakewell, Haddon Hall, & scenic walks. Perfect base for Derbyshire adventures, walking holidays, family trips or romantic weekends. Fast WiFi, smart check-in, family friendly. Popular hiking trails & cycle routes on the doorstep. Great choice of nearby cafes, farm shops, & country pubs.

Guest favorite
A wooden entrance door is framed by large planters filled with vibrant flowers and lush greenery. The glass panels of the door are partially frosted, allowing light to filter through. The surrounding area is adorned with hanging baskets overflowing with colorful blooms.
Condo in Dronfield
4.82 out of 5 average rating, 257 reviews

Exclusive & Beautiful Modern Studio Flat

Located on Green Lane, traffic is busy at peak times of the day, however this private studio is perfect for access to the Peak District. There is a kitchen, a spacious bathroom, pull-down double bed (only a small 4 ft double). The flat is best suited for a single person but if you are in a couple and the bed is ok, then this will suit you. The Peak district is just a short car ride away. Restaurants, supermarkets; train station and buses will take you to Sheffield or chesterfield.

Top guest favorite
Condo in Derbyshire
4.99 out of 5 average rating, 148 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, 339 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

Popular amenities for Chesterfield vacation rentals

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$18,843 GYDG$19,052 GYDG$19,471 GYDG$20,937 GYDG$21,146 GYDG$21,146 GYDG$23,030 GYDG$24,915 GYDG$21,774 GYDG$22,402 GYDG$21,984 GYDG$20,937 GYD
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 50 vacation 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 40 homes with free parking, over 50 homes with a kitchen, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Chesterfield?

    Four-legged friends are welcome in Chesterfield. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Chesterfield?

    Chesterfield has more than 60 family-friendly stays. 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 apartment rentals in Chesterfield?

    Experience the best of Chesterfield with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chesterfield have wifi?

    Absolutely! We offer over 60 house 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 Brimington, and over 180 vacation rentals in Chesterfield.

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 G$4,187 GYD 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