Holiday rentals in Chesterfield District

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Top-rated holiday rentals in Chesterfield District

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Top guest favourite
A well-maintained pathway leads to a beautifully designed cottage surrounded by lush greenery. The property features manicured hedges and trees, with a clear blue sky overhead, creating a welcoming entrance to the private garden area.
Guest house in Derbyshire
4.99 out of 5 average rating, 185 reviews

Springwood Cottage Private and Unique

Springwood Cottage is ideally situated in a beautiful location on the edge of Derbyshire is completely self contained with its own entrance and private garden area with parking outside. The Cottage is completely newly built in 2020 and designed to the highest standard. Well behaved Dogs welcome, we are happy to accommodate 2 dogs, please request if you have more than 2. A deluxe super kingsized bed (6 x6 foot) with the most up to date memory foam mattress and a comfortable sofa bed in the lounge

Top guest favourite
Cottage in Chesterfield
4.93 out of 5 average rating, 320 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.

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 in Bolsover
5 out of 5 average rating, 213 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.

Top guest favourite
Flat in Chesterfield
4.96 out of 5 average rating, 289 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 Derbyshire
4.9 out of 5 average rating, 105 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
The exterior of the Coach House features a charming stone facade with a moss-covered roof. Two garage doors, framed by flower pots, provide a warm welcome. A gravel driveway surrounds the building, complementing the tranquil setting among mature trees.
Flat in Harthill
4.99 out of 5 average rating, 141 reviews

The Coach House Harthill

The Coach House is the beautifully converted annex of ‘The Old Rectory’; a very handsome Grade II listed seven-bedroom period home built by the son of the 1st Duke of Leeds back in 1720, in the pretty village of Harthill. It offers the perfect location to explore Sheffield and the surrounding Peak District, conveniently situated close to the M1 (Junction 30) and A57. The bright and spacious living area comprises a kitchen, bathroom and two bedrooms and has off road parking for two cars.

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 in Chesterfield
4.97 out of 5 average rating, 346 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
Barn in Holymoorside
4.99 out of 5 average rating, 170 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 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 in Derbyshire
4.95 out of 5 average rating, 344 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
Apartment in Chesterfield
4.84 out of 5 average rating, 140 reviews

2 Bed Apartment at the Corner House - Town Centre

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.

Guest favourite
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.
Flat in Hollingwood
4.87 out of 5 average rating, 183 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 favourite
A vibrant green snooker table is positioned in the center of the games room. A triangle of red balls rests at one end, with a single black ball placed nearby. A large television and seating area are visible in the background.
Home in Ecclesfield
4.99 out of 5 average rating, 177 reviews

Exclusive Detached Retreat+Games Room M1J35 1.5m

A unique duplex property that has a fully furnished games room complete with snooker table, professional air hockey table, surround sound cinema system with a self contained upstairs living space equipped to a high standard. Located in the heart of Ecclesfield you are a short distance from local amenities, woodland walks, pubs and cafes but also only a short distance to the vibrant nightlife in Sheffield. .

Popular amenities for Chesterfield District holiday rentals