
Family-friendly holiday rentals in Chesterfield
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Chesterfield

Total holiday rentals
Explore 70 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $57 AUD per night before taxes and fees

Verified guest reviews
Over 4,520 verified reviews to help you choose

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Chesterfield holiday 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!
Top-rated family-friendly rentals in Chesterfield
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Springwood Cottage Private and Unique
Springwood Cottage is ideally situated in a beautiful location on the edge of Derbyshire is completely self contained with its own entrance and private garden area with parking outside. The Cottage is completely newly built in 2020 and designed to the highest standard. Well behaved Dogs welcome, we are happy to accommodate 2 dogs, please request if you have more than 2. A deluxe super kingsized bed (6 x6 foot) with the most up to date memory foam mattress and a comfortable sofa bed in the lounge
KitchenFamilyHeating

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.
FamilyIndoor spacesHospitality

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.
FamilyKitchenSleep quality

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.
FamilyIndoor spacesValue

Chesterfield -Peak District-Chatsworth-EV Charger
Welcome to 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.
Indoor spacesKitchenHospitality

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.
Indoor spacesKitchenBackyard

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
FamilyIndoor spacesShared spaces

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!
Indoor spacesFamilyView

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.
KitchenFamilyBathroom

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.
FamilyKitchenBarbecue

Exclusive Detached Retreat+Games Room M1J35 1.5m
A unique duplex property that has a fully furnished games room complete with snooker table, professional air hockey table, surround sound cinema system with a self contained upstairs living space equipped to a high standard. Located in the heart of Ecclesfield you are a short distance from local amenities, woodland walks, pubs and cafes but also only a short distance to the vibrant nightlife in Sheffield. .
KitchenFamilyWalkability

'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.
KitchenFamilyGetting around
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Lizzy’s Luxury Cottage
Indoor spacesKitchenAmenities

Jack's Cottage, Curbar
Indoor spacesKitchenPets

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

Bridgefoot Cottage - Wild Swimming & Hot Tub
FamilyKitchenCleanliness

Luxury Country Cottage with Hot Tub
Indoor spacesKitchenView

Boulder Field Cabin and Hot Tub
KitchenIndoor spacesAmenities

Cozy Couples Glamping - Private Hot Tub
FamilyKitchenTV

Clover View - Hot tub, Sauna & Countryside Views
KitchenIndoor spacesQuiet
Family- and pet-friendly home rentals

Cosy self contained studio - Peak District
KitchenIndoor spacesComfort

Green Lea - 1 bedroom coach house in SW Sheffield
Indoor spacesFamilyOutdoor spaces

Characterful 2 bed cottage in excellent location
KitchenIndoor spacesGetting around

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views
KitchenFamilyCondition

Beautiful barn conversion.
FamilyKitchenGetting around

Derbyshire Gem, Peak District
FamilyKitchenCheckout

Stretton Hall Farm - The Pod 3
Indoor spacesFamilyCheckout

“Your Sheffield home away from home”
KitchenIndoor spacesLaundry
Family-friendly home rentals with a pool

Boutique Retreat, Summer Pool, Peak District
KitchenFamilyAccess

The Tissington Retreat, Ashbourne Heights
FamilyIndoor spacesGetting around

Swimming Pool Peak Park Cottage 15 Min Alton Tower
FamilyKitchenAccuracy

Cosy Woodside Cottage, indoor pool, nr Chatsworth
Indoor spacesKitchenAccess

Caravan at Ashbourne Heights
KitchenFamilySleep quality

Vale Pool Annex – Countryside Stay near Nottingham
FamilyKitchenSleep quality

Loki’s Lodge@ Ashbourne Heights holiday park
FamilyIndoor spacesComfort

Dog Friendly Retreat
Indoor spacesKitchenHospitality
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $168 AUD | $188 AUD | $190 AUD | $195 AUD | $200 AUD | $202 AUD | $178 AUD | $188 AUD | $171 AUD | $171 AUD | $166 AUD | $174 AUD |
| 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 |
Destinations to explore
- Peak District National Park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- Heaton Park
- Donington Park Circuit
- The Quays
- Didsbury Village
- Lincoln Castle
- AO Arena
- Harewood House
- Bowlers Exhibition Centre
- Tatton Park
- Bramham Park
- Yorkshire Wildlife Park
- University of Manchester
- Manchester Central Convention Complex
- Wythenshawe Park
- University of Leeds
- The Piece Hall
- Belvoir Castle
- Temple Newsam Park
- Motorpoint Arena Nottingham
- Royal Armouries Museum





