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 in New Tupton
4.87 out of 5 average rating, 351 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 in Wingerworth
4.89 out of 5 average rating, 271 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 in Derbyshire
4.93 out of 5 average rating, 148 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
4.86 out of 5 average rating, 102 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, 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 in Wingerworth
4.94 out of 5 average rating, 301 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
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, 254 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 in Derbyshire
4.99 out of 5 average rating, 136 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.

Top guest favorite
Guest suite in Ashover
4.98 out of 5 average rating, 355 reviews

Cosy self contained studio - Peak District

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.

Top guest favorite
A modern kitchen area is showcased with sleek white cabinetry and a dark countertop. Essential appliances, including an oven, refrigerator, and washing machine, are visible. Light wooden flooring runs throughout the space, and a piece of wall art depicting a beach scene is hung on a light grey wall.
Guesthouse in Denby Village
4.9 out of 5 average rating, 176 reviews

Beautiful place in the heart of Derbyshire

Beautiful outbuilding situated in the heart of Derbyshire. Outbuilding separated from main house. Shared garden with stunning views of the countryside. This property has its own private entrance and includes off road parking. We live within a quiet small estate that is situated in the heart of Derbyshire. lots of little towns ,Belper is a lovely town with river gardens and lovely boutiques for shopping. Fancy walking or bike riding why not visit matlock or the peak district

Superhost
The studio features a spacious bed adorned with floral bedding, complemented by soft lighting from bedside lamps. A wicker sofa is positioned nearby, providing a cozy seating option. Cabinets and a small kitchenette are visible, along with a touch of artwork on the wall.
Guesthouse in Bolsover
4.73 out of 5 average rating, 119 reviews

Studio with privacy and own space

The listing is for a studio/bedsit which is situated on our back garden. It has its own entrance with a double glazed door with lock. You would have your own parking space off the road and the studio is accessed up the drive and onto the garden. You will have free wifi and also full sky television in the studio. There is a shower room as well. We are situated in a quiet area not on an estate and our home is a detached bungalow on a row of detached bungalows.

Guest favorite
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
4.87 out of 5 average rating, 179 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.

Popular amenities for Chesterfield family-friendly rentals

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Avg. priceﺩ.ﺇ389ﺩ.ﺇ386ﺩ.ﺇ404ﺩ.ﺇ408ﺩ.ﺇ426ﺩ.ﺇ441ﺩ.ﺇ448ﺩ.ﺇ448ﺩ.ﺇ452ﺩ.ﺇ426ﺩ.ﺇ415ﺩ.ﺇ411
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Quick stats about vacation rentals that are family-friendly in Chesterfield

  • Total vacation rentals

    Explore 60 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 3,750 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 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!