
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 $51 SGD per night before taxes and fees

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

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 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!
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.
Indoor spacesFamilySleep quality

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.
Indoor spacesFamilyValue

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
KitchenIndoor spacesLong stay

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 spacesFamilyView

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.
FamilyKitchenAccess

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

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.
KitchenIndoor spacesNearby

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 spacesSleep quality

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
Indoor spacesFamilyHiking

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!
KitchenFamilyCondition

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.
FamilyIndoor spacesAir conditioning

'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 spacesKitchenSleep quality
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

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

A Hidden Gem - Farmhouse with Hot Tub & Games Room
Indoor spacesFamilyView

Bridgefoot Cottage - Wild Swimming & Hot Tub
KitchenFamilyLaundry

Peak District Home from Home!
FamilyIndoor spacesAccess

Hazel Lodge luxury log cabin
Indoor spacesKitchenSleep quality

Atlow Mill - award winning 5 bed accommodation
FamilyKitchenWalkability

Runner Duck Cottage
KitchenFamilyGetting around

Luxury Cottage Green Cottage, Peak District
FamilyIndoor spacesCondition
Family- and pet-friendly home rentals

Lovely apartment above cafe near Peak District
FamilyKitchenLocation

Wasp Nest Cottage, Peak District
KitchenIndoor spacesBreakfast

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views
KitchenIndoor spacesLayout

Cosy self contained studio - Peak District
FamilyKitchenLaundry

Beautiful barn conversion.
KitchenFamilyHeating

Characterful 2 bed cottage in excellent location
KitchenFamilyRiver

The Stables
KitchenIndoor spacesWalkability

Springwood Cottage Private and Unique
FamilyKitchenBathroom
Family-friendly home rentals with a pool

The Round House - family house with indoor pool
KitchenFamilyDecor

Boutique Retreat, Summer Pool, Peak District
KitchenFamilyLayout

Swimming Pool Peak Park Cottage 15 Min Alton Tower
KitchenFamilySleep quality

Dog Friendly Ground Floor Cottage with Shared Pool
KitchenFamilyCheckout

Luxury Shepherd's Retreat with Hot Tub
FamilyIndoor spacesComfort

Romantic Peak District Spa Cottage •Hot Tub & Pool
FamilyKitchenGetting around

Dog Friendly Retreat
Indoor spacesKitchenNearby

Winnow Nook - romantic getaway for 2
KitchenIndoor spacesAccess
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $151 SGD | $168 SGD | $170 SGD | $175 SGD | $179 SGD | $181 SGD | $160 SGD | $168 SGD | $153 SGD | $153 SGD | $148 SGD | $156 SGD |
| 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
- The Quays
- Donington Park Circuit
- Didsbury Village
- Lincoln Castle
- AO Arena
- Harewood House
- Tatton Park
- Wythenshawe Park
- University of Manchester
- Bowlers Exhibition Centre
- Yorkshire Wildlife Park
- Bramham Park
- Manchester Central Convention Complex
- Temple Newsam Park
- The Piece Hall
- Yorkshire Sculpture Park
- Mam Tor
- Belvoir Castle
- Manchester Central Library





