Vacation rentals in Chesterfield

4.92 out of 5 average rating, 299 reviews

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

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 suite in New Tupton

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.

4.87 out of 5 average rating, 346 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.

4.88 out of 5 average rating, 263 reviews

A spacious garden area is visible, featuring a variety of colorful flowers in pots, including bright yellow and pink blooms. A well-maintained lawn extends into the distance, accompanied by tree line and greenery. A soft play structure and garden shed are also included in the scene.

Home in Wingerworth

Oakdale - Our Quest retreat

Idyllically situated at the entrance to Hardwick Wood, Wingerworth, 2 miles from Chesterfield and all amenities, yet totally secluded. Close to Chatsworth & Peak District. Fully fitted kitchen all appliances including tumble drier & dishwasher. Underfloor zoned central heating. Log burner. Fully fitted bathroom with bath and shower. Separate shower/wc. Fully fitted bedrooms with ample wardrobes and drawers ideally suited to a family of 4. Sleeps 4 in one double and 1 set of bunks, cot available

The entrance to the home features a well-maintained path leading to a white door, flanked by decorative planters with colorful flowers. Lush greenery and shrubs enhance the welcoming atmosphere, and a charming arrangement of potted plants adds to the inviting entryway.

4.98 out of 5 average rating, 113 reviews

Home from Home with private rose garden

Modern cosy family home on the edge of the beautiful Peak District with private garden and off road parking. Newly re-furbished. Just right for visiting famous places i.e. Chatsworth House, Bakewell for a Bakewell pudding, the caves at Castleton, walking/mountain biking on the beautiful moors or just meeting up with friends or relatives. Good bus service to town centre and the famous Crooked Spire. Local shops, restaurant, take-away, chemist within easy walking distance or 2 mins by car.

Guest suite in Wingerworth

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.

4.95 out of 5 average rating, 292 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.

4.82 out of 5 average rating, 249 reviews

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

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.

4.99 out of 5 average rating, 130 reviews

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

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.

4.97 out of 5 average rating, 327 reviews

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

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

5 out of 5 average rating, 145 reviews

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

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.

4.98 out of 5 average rating, 350 reviews

A well-arranged bedroom features a spacious bed with decorative pillows and a cozy quilt. A window with striped blinds provides natural light and a view of greenery outside. An ice bucket and two glasses are placed on a bedside table, adding a touch of elegance.

Guest suite in Ashover

Hunger Hill Farm Studio - Derbyshire Dales

Set in the glorious Peak District in a rural and peaceful location is our lovely self contained studio. Glorious views and walks over rolling countryside. Close to Chatsworth House and Haddon Hall. With the popular wedding venue (Peak Edge Hotel ) within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here. Perfect for the Chatsworth Christmas market.

Apartment in Sheffield/Chesterfield

A bright and open studio space features a comfortable double bed with crisp white linens. A cozy seating area includes soft armchairs and a dining table set for four. Light wood accents and a floral wallpaper create a calming ambiance.

4.99 out of 5 average rating, 176 reviews

Peaceful setting, close to amenities and transport

The Milking Parlour is a single storey studio, it is in a quiet enclave composing of a farmhouse, and various renovated farm buildings making up 4 residences. We are situated about 50m from the main road and bus stops for regular direct buses to Sheffield/Chesterfield . Dronfield has a train station providing an hourly service direct to London. 1 mile from the Derbyshire countryside, 10miles - Chatsworth House, 12 miles - Bakewell.

4.86 out of 5 average rating, 174 reviews

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

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.

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Popular amenities for Chesterfield vacation rentals

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Free parking on premises

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Other great vacation rentals in Chesterfield

Apartment in Chesterfield

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.

4.96 out of 5 average rating, 280 reviews

Cosy studio apartment close to Peak District

The modern kitchen is equipped with light-colored cabinetry and a wooden countertop. Stainless steel appliances include a gas stove, microwave, and kettle. A stone backsplash adds texture, while a wine rack and dishware are neatly organized. Adequate lighting illuminates the workspace.

4.97 out of 5 average rating, 30 reviews

Cosy 2 bed home CHESTERFIELD

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.

4.97 out of 5 average rating, 58 reviews

Home in Chesterfield

4.98 out of 5 average rating, 42 reviews

The exterior of a two-bedroom house is presented, showcasing a brick façade with a gabled roof. A driveway leads to a black vehicle parked beside the entrance. Lush grass borders the pathway, and a clear blue sky is visible overhead.

Home in Walton

Derbyshire Gem, Peak District

4.98 out of 5 average rating, 121 reviews

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

Charming grade II listed cottage with hot tub

A cozy living area is presented with a brown sofa adorned with decorative cushions. A wooden coffee table sits in front, complemented by a patterned area rug. A wall-mounted television and a decorative shelf enhance the space, which is warmed by a stove and illuminated by natural light.

4.88 out of 5 average rating, 59 reviews

The Beehive

A spacious lounge features a large flat-screen television positioned on a wooden media console. A dark coffee table is centered in front of a comfortable sofa adorned with decorative cushions. Natural light streams through the adjacent doorway, enhancing the soft carpeted flooring.

4.96 out of 5 average rating, 24 reviews

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