Holiday rentals in Chesterfield District

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Top-rated holiday rentals in Chesterfield District

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Top guest favourite
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
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.

Guest favourite
The garden studio features a stone exterior with large windows and a welcoming entrance. A gravel path leads to the door, surrounded by blooming flowers and greenery. The roof is gently sloped under a bright blue sky with scattered clouds.
Guest house
4.91 out of 5 average rating, 715 reviews

Garden Loft/Studio Sleeps 2

Nestled in the leafy suburb of Dore, on the edge of the Peak District and Sheffield. Self contained garden studio, with open plan kitchen/living room, shower room and upstairs attic style bedroom with double bed , sloping ceiling with some restricted height,& garden view. Private garden space & alfresco dining area for own use. May not be suitable for very overweight, tall or elderly people due to height restrictions and narrow stairs. Please feel free to ask prior to booking if any concerns.

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, 181 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
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.
Apartment
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 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
4.94 out of 5 average rating, 158 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, 105 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
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
4.94 out of 5 average rating, 308 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 favourite
Cottage
4.97 out of 5 average rating, 36 reviews

Pet-Friendly Cosy Cottage in Chesterfield

Escape to our charming 2-bedroom cottage in Chesterfield, Derbyshire. Perfect for couples, friends, or small families, the cottage offers cozy bedrooms, a fully equipped kitchen, and a welcoming living area. Just minutes from the town center, local shops, and the Peak District, it’s an ideal base for exploring, relaxing, and enjoying the best of Derbyshire. Comfort, convenience, and charm await you. Perfect base for those travelling with their furry friends, as a pet friendly stay.

Top guest favourite
Apartment
4.99 out of 5 average rating, 153 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 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, 341 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
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
4.95 out of 5 average rating, 310 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

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, 139 reviews

2 Bed Apartment at the Corner House

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.

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