Family-friendly vacation rentals in Chesterfield

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Top-rated family-friendly rentals in Chesterfield

Guests agree: these family-friendly homes 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
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 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
4.88 out of 5 average rating, 269 reviews

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

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
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
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
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
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
4.96 out of 5 average rating, 283 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
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.

Superhost
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
4.82 out of 5 average rating, 252 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
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
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
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
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
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
4.96 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

Popular amenities for Chesterfield family-friendly rentals

Quick stats about vacation rentals that are family-friendly in Chesterfield

  • Total rentals

    60 properties

  • Nightly prices starting at

    € 43 before taxes and fees

  • Total number of reviews

    3.8K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 properties include access to wifi