Family-friendly holiday rentals in Chesterfield

4.93 out of 5 average rating, 343 reviews

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.

A spacious outdoor area features a hot tub alongside a wooden pod structure. Stone tiles lead to steps that access the hot tub, while a small table can be seen nearby. Natural greenery borders the patio, providing a serene backdrop.

4.96 out of 5 average rating, 160 reviews

Spa Home with Hottub, Sauna Pool Table

Spa home with sauna, hottub, all modern amenities, on the edge of the Peak District and just 5 minutes walk from Chesterfield train station. 1pm check-in. Perfect for all experiences, extra large bedrooms. There is full-sized pool table, BBQ area, Sonos music, log-burner, open-plan kitchen and living areas. Ideal for several families or large group getaways. Prime location allows you to enjoy the Derbyshire countryside whilst being within walking distance of a multitude of cafes, shops and bars.

4.87 out of 5 average rating, 320 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

5.0 out of 5 average rating, 248 reviews

A spacious detached house is surrounded by lush greenery and landscaped grounds. The exterior features a stone facade, slate roof, and charming gardens with flowering plants. Free-roaming chickens are visible, adding a rural charm to the serene setting under a clear blue sky.

Home in Youlgreave

The Stables House, Lomberdale Hall. 4 to 7 guests

Spacious detached private house, 3,000 sq ft/ 275 sq m. Own drive. 3 acres of grounds. Log burner (fuel provided) Front, back and garden doors; Entrance hall, sweeping staircase, beautiful sitting room, library stuffed with books, 3 large bedrooms (Vispring beds) plus 3 fab bathrooms with baths & separate showers - plus a single bed downstairs. Warm kitchen, utility room & larder. Antique furniture, lovely curtains. Perfect for families, couples, groups. Walking galore! 3 Pubs in the village.

Apartment in Chesterfield

A bedroom is featured with a spacious bed dressed in floral bedding. A wooden wardrobe with mirrors stands beside the bed. A bedside lamp provides soft illumination, while neatly folded towels are placed at the foot of the bed, offering a sense of comfort and convenience.

4.85 out of 5 average rating, 102 reviews

The Hideaway

Surround yourself with style in this standout space. Modern recently refurbished basement apartment with secure drive. It comprises of 1 bedroom with king size bed with Premier Inn mattress. It has a kitchen/lounge with pull out sofa bed that sleeps 2. The kitchen is equipped with microwave, fridge, air fryer, kettle, toaster and all utensils. Includes all bedding and towels. Shower room. 10 min walk to the chesterfield canal. Shops, pubs and restaurants are all within walking distance.

Townhouse in Chesterfield

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.

4.86 out of 5 average rating, 117 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.

An inviting living space is featured, showcasing a modern dining table and chairs alongside a vibrant red sideboard. A cozy armchair and a striped lounge chair add comfort, while softly illuminated pendant lights enhance the room's ambiance. Natural light filters through a window adorned with gray curtains.

4.91 out of 5 average rating, 114 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.

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, 294 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.

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.

4.96 out of 5 average rating, 352 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

4.99 out of 5 average rating, 196 reviews

Barn in Holymoorside

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!

4.82 out of 5 average rating, 146 reviews

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.

Condo in Chesterfield

The Corner House A-2 Bedroom Town Centre Apartment

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.

4.87 out of 5 average rating, 185 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.

Popular amenities for Chesterfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 224 reviews

Cottage in Letwell

Rural cottage! Wood-fired hot tub. Bliss awaits.

4.81 out of 5 average rating, 222 reviews

An aerial view of the Farmhouse at Fallinge Farm reveals its stone exterior set amidst lush greenery. The surrounding gardens feature various trees and flower beds, with a winding pathway leading to the property. The expansive grounds extend into open fields, highlighting the rural landscape.

Farm stay in Rowsley

A Hidden Gem - Farmhouse with Hot Tub & Games Room

4.89 out of 5 average rating, 297 reviews

A view from a bridge showcases a serene countryside scene with a stone cottage nestled among lush greenery. The vibrant leaves of trees frame the picturesque surroundings, while the calm waters of the river reflect the natural beauty. The distant hills provide a backdrop.

Home in Grindleford

Bridgefoot Cottage - Wild Swimming & Hot Tub

4.85 out of 5 average rating, 415 reviews

The exterior of the stone cottage is featured, showcasing its classic design with multiple windows and a welcoming entrance. Hanging flower baskets add a touch of greenery, while the surrounding landscape displays lush grassland and rolling hills in the distance.

Home in Derbyshire

Runner Duck Cottage

4.91 out of 5 average rating, 122 reviews

A warm living area is adorned with an orange sofa, layered with decorative pillows. A low table rests atop a patterned rug, while a guitar leans against a natural wood shelf featuring books and plants. Two windows invite natural light into the space.

Home in Grindleford

Peak District Home from Home!

4.99 out of 5 average rating, 299 reviews

A charming outdoor area features a gray hydrotherapy hot tub surrounded by lush greenery. Nearby, pastel pink chairs invite relaxation, with towels neatly arranged and a small table presenting refreshments. The rustic stone wall adds character to the private garden setting.

Cottage in Derbyshire

Jack's Cottage, Curbar

4.98 out of 5 average rating, 121 reviews

An open plan kitchen features a large island with a light stone countertop, complemented by three pendant lights above. Skylights influence natural light, illuminating the space, while a wall-mounted clock adds a decorative touch. A living area with a TV and seating is visible in the background.

Home in Nottinghamshire

5 Bed luxury holiday home

4.99 out of 5 average rating, 174 reviews

The exterior of a beautifully renovated stone cottage is depicted, featuring a hot tub on a wooden deck. Large windows reflect natural light, while a manicured lawn surrounds the cottage, enhancing the inviting ambiance of the tranquil setting.

Cottage in Alton

Luxury Cottage Green Cottage, Peak District

Family- and pet-friendly home rentals

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.

4.97 out of 5 average rating, 103 reviews

Derbyshire Gem, Peak District

4.91 out of 5 average rating, 306 reviews

A safari tent is situated on a raised wooden deck, accessible by a set of wide stairs. The tent features a green canvas exterior with wooden accents. Surrounding grassy areas are visible, and the sky above is partly cloudy, suggesting a pleasant outdoor environment.

Tent in Ashover

Private Safari Tent, sleeps 4, Ashover, Derbyshire

4.82 out of 5 average rating, 270 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

4.95 out of 5 average rating, 346 reviews

A cosy living room features comfortable seating on two plush sofas, arranged around a central ottoman. A stone fireplace with a woodburner creates a focal point. Exposed beams highlight the ceiling, while the space is adorned with floral cushions and a decorative area rug.

Cottage in Baslow

Characterful 2 bed cottage in excellent location

4.98 out of 5 average rating, 234 reviews

A traditional stone barn conversion is visible, showcasing a well-maintained exterior with multiple windows and doors. The surrounding gravel driveway leads to a serene countryside setting, highlighted by greenery in the background and a clear blue sky above.

Condo in Holymoorside

Dog Friendly, Cosy, Peaceful, Walks, Peak District

4.99 out of 5 average rating, 196 reviews

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.

Guesthouse in Derbyshire

Springwood Cottage Private and Unique

5.0 out of 5 average rating, 282 reviews

A spacious lawn leads to a charming stone cottage, surrounded by well-maintained greenery. The bright blue sky and scattered clouds enhance the inviting atmosphere, while the driveway provides access to the property and its scenic surroundings.

Cottage in Derbyshire

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

4.97 out of 5 average rating, 348 reviews

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 in Holymoorside

Wasp Nest Cottage, Peak District

Family-friendly home rentals with a pool

4.85 out of 5 average rating, 214 reviews

An indoor heated swimming pool is featured with a rounded design, surrounded by large glass windows that provide natural light and views of the outdoors. Two steps lead into the pool, which is bordered by a tiled area. Loungers are placed nearby for relaxation.

Cottage in Rowsley

Cosy Woodside Cottage, indoor pool, nr Chatsworth

4.83 out of 5 average rating, 101 reviews

The entrance to the cottage is framed by rustic brick and stone walls. A wooden door with glass panels provides access, while a small outdoor area features a round table and two chairs on pebbled ground. A welcome sign is visible above the door.

Cottage in Brassington

Dog Friendly Ground Floor Cottage with Shared Pool

4.95 out of 5 average rating, 412 reviews

Cottage in Fenny Bentley

Boutique Retreat, Summer Pool, Peak District

4.98 out of 5 average rating, 129 reviews

A rustic retreat is positioned among tall trees, accented by well-maintained landscaping. Stone steps lead to a wooden structure featuring large glass doors. Outdoor seating is visible on the patio, surrounded by a variety of green and flowering plants, under a clear blue sky.

Shepherd’s hut in Warsop

Luxury Shepherd's Retreat with Hot Tub

4.8 out of 5 average rating, 142 reviews

A serene outdoor setting features a circular stone table surrounded by four black metal chairs. A natural pond with overgrown vegetation is visible, with a rural stone house in the background. The landscape reflects a tranquil countryside atmosphere, complemented by bare trees and scattered plant life.

Guesthouse in Derbyshire

Dog Friendly Retreat

4.82 out of 5 average rating, 137 reviews

The private terrace features a hot tub with views of rolling green hills under a clear blue sky. A comfortable seating area is visible, providing a serene spot to relax and enjoy the landscape, bordered by lush greenery and a stone wall.

Cottage in Derbyshire

Romantic Peak District Spa Cottage •Hot Tub & Pool

4.99 out of 5 average rating, 142 reviews

A four-poster bed is positioned in a softly lit room, accentuated by exposed wooden beams above. A neutral-toned blanket adds warmth to the bed, while a dresser and bedside table complete the cozy atmosphere. Natural light filters through a window with delicate curtains.

Cottage in Ashbourne

Winnow Nook - romantic getaway for 2