Family-friendly holiday rentals in Chesterfield

4.93 out of 5 average rating, 344 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.

4.87 out of 5 average rating, 322 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

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.

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.

4.85 out of 5 average rating, 102 reviews

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.

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.

4.86 out of 5 average rating, 117 reviews

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.

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.

4.96 out of 5 average rating, 294 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.

4.96 out of 5 average rating, 353 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, 198 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!

4.96 out of 5 average rating, 224 reviews

Cottage in Letwell

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

Welcome to our home! A charming cottage in a rural village, ideal for couples, families, friends, contractors, business trips & weddings. The property features 2 king-size bedrooms, a children’s bedroom with 3 single beds, plus a ground-floor king bedroom & 3 bathrooms. Enjoy a bespoke kitchen, rain shower, wood burner, parquet flooring, huge garden with play area, hot tub & parking for 3 cars/LWB van. Close to M1, A1, Hodsock Priory, Thoresby, Sherwood Forest & Sheffield.

4.82 out of 5 average rating, 147 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.

4.95 out of 5 average rating, 450 reviews

A cozy bedroom is showcased with a spacious bed and a bedside table featuring a warm lamp. A doorway leads to a stable where a black pony can be seen peering over a wooden barrier. Soft hay is visible in the stable area.

Farm stay in Thurgarton

Sleepover with Miniature horse Basil

Basils Barn is situated on the grounds of a 17th century manor, surrounded by a picturesque 60 acre estate. The bedroom is directly attached to Basils stable, where there is a doorway in between the two spaces. In the paddocks we also have a herd of Highland cows, Hebridean sheep, horses, pigs, chickens and Norwegian Forrest cats. Our animals are mostly rescued and all of our animals are kept strictly as pets.

A modern two-story home features a clean white exterior with large windows and a circular accent window. A wooden fence offers privacy to the front yard, which displays a paved pathway leading to the entrance. The sky is partly cloudy, creating a serene backdrop.

4.98 out of 5 average rating, 282 reviews

'Rose House' Modern 3 Bedroom Detached House

Located a mile from Chesterfield town centre. The property consists of a large open plan lounge/kitchen, 2 double bedrooms and 1 single room with bunk beds. The garden is south facing and there is private parking. There are a range of bars, cafe's, restaurants and local amenities just a short walk from the property. Chatsworth House, Haddon Hall and Peak District are 15 minutes drive away.

Popular amenities for Chesterfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 123 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!

4.81 out of 5 average rating, 223 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, 299 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, 419 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

4.97 out of 5 average rating, 253 reviews

A wide-open green landscape is depicted, featuring rolling hills under a cloudy sky. A single dark horse stands in the foreground, surrounded by scattered trees and lush grass, highlighting the serene natural environment.

Cottage in Alstonefield

Modern cottage in a stunning Peak District setting

4.94 out of 5 average rating, 291 reviews

A charming stone exterior is adorned with vibrant flower pots of various colors, arranged beside a lovely staircase. A quaint garden path leads to a green door, complemented by neatly trimmed hedges and additional potted plants enhancing the welcoming atmosphere.

Farm stay in Butterton

Hot Tub Indoor Pool Peak Park 15 mins Alton Towers

4.96 out of 5 average rating, 204 reviews

An outdoor space features a cozy seating area with four circular chairs surrounding a firepit. A wooden deck leads to a converted tour bus, while a wood-fired hot tub is positioned nearby. String lights hang above, adding a warm touch to the setting.

Tiny home in Alton

The Old Tour Bus. Hot tub and treetop cinema!

4.92 out of 5 average rating, 155 reviews

A charming stone barn exterior is framed by lush greenery. The building features several windows and is adorned with climbing vines and red leaves, creating a natural connection with its surroundings. A stone pathway leads to the entrance, enhancing the inviting appearance.

Home in Derbyshire

Hugo’s Luxury Barn

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, 307 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

4.97 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

4.94 out of 5 average rating, 348 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

4.94 out of 5 average rating, 455 reviews

The exterior of the stone cottage is framed by a vibrant garden filled with colorful flowers. Large windows provide natural light, and solar panels can be seen on the roof. A rustic stone wall adds charm to the property, creating an inviting entrance.

Cottage in Matlock

17th century cottage in Matlock

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

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

4.98 out of 5 average rating, 393 reviews

Guest suite in Ashover

Cosy self contained studio - Peak District

Family-friendly home rentals with a pool

4.85 out of 5 average rating, 215 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

4.95 out of 5 average rating, 413 reviews

Cottage in Fenny Bentley

Boutique Retreat, Summer Pool, Peak District

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

4.98 out of 5 average rating, 132 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

4.99 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

4.83 out of 5 average rating, 138 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