
Family-friendly holiday rentals in Chesterfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesterfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

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

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.

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.

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.

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.

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.

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.

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

Matlock Glamping 'Left' Room - Derbyshire Dales.
Set in the heart of the historic spa town of Matlock, well served by public transport, these newly renovated 'Glamping Rooms' ooze style and comfort. The private room is self contained within the barn, with a shower room/toilet and a cute, fully equipped kitchenette. Ideal for couples but also practical and large enough for a family of six. There is a boot store, bike shed and on-site parking. Breakfasts, packed lunch and evening meals are also available with prior notice.

2 Bed Apartment at the Corner House
A ground floor two double bedroom apartment in a converted 1800s home which has recently undergone further high-spec refurbishment, used solely for guests. The open plan kitchen/diner holds a sofa bed is perfect for a relaxing stay. The property is within walking distance to Chesterfield town centre and train station with an allocated parking space for one car. This is perfect for anyone commuting or working in the area as well as visiting the Peak District.

Peaceful setting, close to amenities and transport
The Milking Parlour is a single storey studio, it is in a quiet enclave composing of a farmhouse, and various renovated farm buildings making up 4 residences. We are situated about 50m from the main road and bus stops for regular direct buses to Sheffield/Chesterfield . Dronfield has a train station providing an hourly service direct to London. 1 mile from the Derbyshire countryside, 10miles - Chatsworth House, 12 miles - Bakewell.
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Hunters Cottage. Wheatsheaf Mews

Lizzy’s Luxury Cottage

Jack's Cottage, Curbar

Luxury Peak District Cottage with Hot Tub

Pear Tree Lodge with private HOT TUB and garden

The Granary

Luxury Shepherds Hut Retreat with Hot tub

Beautiful, private 2 bedroom Annex with Hot Tub
Family- and pet-friendly home rentals

17th century cottage in Matlock

Pepper Cottage- pet-friendly, stylish & cosy

Cosy cottage, stunning views near Chatsworth

Holly Cottage a great place for a country break

Pedaller's Rest

Charming fully equipped home 5min to Peak District

Riverbank Cottage - Annex

Quaint 2 bed cottage, ideally located for walking
Family-friendly home rentals with a pool

Caravan near Tissington Trail

Luxury Peak District Home - 2 miles from Ashbourne

Two bed annex apartment

Indoor Pool & Gorgeous Cosy Cottage, Peak District

Cosy Woodside Cottage, indoor pool, nr Chatsworth

home from home

Loki’s Lodge@ Ashbourne Heights holiday park

Family Home Getaway - Hot Tub, Sauna & Swim Spa
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £80 | £79 | £83 | £84 | £88 | £91 | £95 | £101 | £92 | £89 | £86 | £85 |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
Quick stats about holiday rentals that are family-friendly in Chesterfield

Total holiday rentals
Explore 60 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at £38 per night before taxes and fees

Verified guest reviews
Over 3,750 verified reviews to help you choose

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Chesterfield holiday rentals include wifi 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!
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- Peak District national park
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- The Quays
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- Mam Tor
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