Family-friendly vacation rentals in Chesterfield

4.93 out of 5 average rating, 347 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.

KitchenFamilyLong stay

4.87 out of 5 average rating, 326 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

Indoor spacesKitchenComfort

5.0 out of 5 average rating, 250 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.

Indoor spacesKitchenDecor

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.

Indoor spacesKitchenGrill

4.86 out of 5 average rating, 104 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.

FamilyIndoor spacesWalkability

4.87 out of 5 average rating, 119 reviews

4.91 out of 5 average rating, 116 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.

Home in Chesterfield

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.

Indoor spacesKitchenDecor

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.

KitchenIndoor spacesBreakfast

4.96 out of 5 average rating, 296 reviews

4.96 out of 5 average rating, 355 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

KitchenFamilyPets

4.82 out of 5 average rating, 148 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.

KitchenIndoor spacesSolo travel

4.87 out of 5 average rating, 186 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.

Indoor spacesKitchenCleanliness

4.95 out of 5 average rating, 456 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.

Indoor spacesKitchenHot tub

4.98 out of 5 average rating, 284 reviews

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.

Home in Chesterfield

'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.

Indoor spacesFamilyHiking

Popular amenities for Chesterfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 203 reviews

Barn in Holymoorside

Charming grade II listed cottage with hot tub

KitchenIndoor spacesLong stay

4.96 out of 5 average rating, 227 reviews

Cottage in Letwell

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

FamilyIndoor spacesDecor

4.95 out of 5 average rating, 107 reviews

The cabin is framed by vibrant greenery, showcasing wooden exterior features. A balcony extends from the upper level, where seating is visible. The surrounding woodland creates a serene backdrop, with varied foliage contributing to a tranquil atmosphere in the outdoor space.

Cabin in Matlock

Owl Cabin, Coppertop Wood. Hot tub

KitchenIndoor spacesTV

4.88 out of 5 average rating, 303 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

FamilyKitchenView

4.9 out of 5 average rating, 125 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!

KitchenIndoor spacesSleep quality

4.98 out of 5 average rating, 324 reviews

A spacious wooden deck is highlighted, featuring a dining table and chairs set for outdoor meals. Lush greenery surrounds the area, with distant hills visible under a cloudy sky. Large glass doors lead into the lodge, allowing natural light to enter.

Cabin in South Wingfield

Hazel Lodge luxury log cabin

FamilyIndoor spacesPets

4.98 out of 5 average rating, 124 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

KitchenIndoor spacesHospitality

4.99 out of 5 average rating, 178 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

Indoor spacesKitchenSleep quality

Family- and pet-friendly home rentals

4.86 out of 5 average rating, 311 reviews

Condo in Barlow

Lovely apartment above cafe near Peak District

KitchenIndoor spacesWalkability

4.98 out of 5 average rating, 394 reviews

Guest suite in Ashover

Cosy self contained studio - Peak District

Indoor spacesFamilyHospitality

4.99 out of 5 average rating, 178 reviews

A spacious interior features a warm wood-burning stove adjacent to a comfortable sleeping area. Two inviting armchairs are placed upon a soft area rug. Natural light streams in through the skylight and window, illuminating the simple, yet elegant decor.

Barn in Ashover

Beautiful barn conversion.

FamilyKitchenNearby

5.0 out of 5 average rating, 287 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

Indoor spacesKitchenCheck-in

4.82 out of 5 average rating, 272 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

FamilyKitchenLayout

5.0 out of 5 average rating, 200 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

KitchenFamilyView

4.94 out of 5 average rating, 352 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

FamilyKitchenGetting around

4.99 out of 5 average rating, 101 reviews

Houseboat in Brimington

Slinky The Narrow Boat

Indoor spacesKitchenCleanliness

Family-friendly home rentals with a pool

4.84 out of 5 average rating, 293 reviews

An indoor heated swimming pool is framed by large wall-length windows, offering ample natural light. The pool features a curved shape with metal steps leading into the water. Lounge chairs are positioned nearby, inviting relaxation beside the serene water.

Home in Rowsley

The Round House - family house with indoor pool

Indoor spacesFamilyOutdoor spaces

4.95 out of 5 average rating, 417 reviews

Cottage in Fenny Bentley

Boutique Retreat, Summer Pool, Peak District

Indoor spacesKitchenValue

4.83 out of 5 average rating, 102 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

Indoor spacesKitchenParking

4.92 out of 5 average rating, 235 reviews

A stone cottage is viewed from a sunlit patio adorned with vibrant flower pots. The structure features light green accents on windows and doors, surrounded by a natural landscape. A rustic stone wall provides framing, enhancing the serene outdoor setting.

Farm stay in Butterton

Swimming Pool Peak Park Cottage 15 Min Alton Tower

Indoor spacesKitchenHospitality

4.99 out of 5 average rating, 134 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

FamilyKitchenHospitality

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

Indoor spacesFamilyHot tub

4.99 out of 5 average rating, 144 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

FamilyIndoor spacesGrill