
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 $70 NZD 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, Wi-Fi 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.
KitchenIndoor spacesOutdoor spaces
4.93 out of 5 average rating, 346 reviews
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 spacesFamilyCheck-in
4.87 out of 5 average rating, 326 reviews
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 spacesFamilyHeating
4.86 out of 5 average rating, 104 reviews
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.
Indoor spacesFamilyBackyard
4.86 out of 5 average rating, 118 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.
FamilyKitchenCheck-in
4.91 out of 5 average rating, 116 reviews
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.
Indoor spacesFamilyAmenities
4.96 out of 5 average rating, 296 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
FamilyIndoor spacesPets
4.96 out of 5 average rating, 355 reviews
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.
FamilyKitchenParking
4.82 out of 5 average rating, 148 reviews
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.
KitchenFamilyWi-Fi
4.87 out of 5 average rating, 186 reviews
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.
KitchenFamilyHospitality
4.95 out of 5 average rating, 456 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.
Indoor spacesKitchenAccess
4.98 out of 5 average rating, 284 reviews
Old Barn Conversion close to the Peak District
This beautiful detached barn conversion has been charmingly renovated, retaining and working with many original features where possible. Tastefully furnished to a very good standard throughout, the open-plan living space has a small/compact kitchen area with a combi/microwave oven and hob. Its stunning beamed vaulted ceiling creates a warm and cosy social environment.
FamilyKitchenView
4.86 out of 5 average rating, 302 reviewsPopular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Charming grade II listed cottage with hot tub
Indoor spacesFamilyLong stay
4.99 out of 5 average rating, 203 reviews
Rural cottage! Wood-fired hot tub. Bliss awaits.
KitchenIndoor spacesAmenities
4.96 out of 5 average rating, 227 reviews
Peak District Home from Home!
Indoor spacesKitchenCondition
4.9 out of 5 average rating, 124 reviews
Bridgefoot Cottage - Wild Swimming & Hot Tub
FamilyKitchenLong stay
4.88 out of 5 average rating, 302 reviews
5 Bed luxury holiday home
FamilyIndoor spacesCheck-in
4.98 out of 5 average rating, 124 reviews
Hazel Lodge luxury log cabin
Indoor spacesKitchenHot tub
4.98 out of 5 average rating, 322 reviews
Runner Duck Cottage
FamilyIndoor spacesBathroom
4.86 out of 5 average rating, 422 reviews
Luxury Cottage Green Cottage, Peak District
KitchenFamilyHiking
4.99 out of 5 average rating, 176 reviewsFamily- and pet-friendly home rentals

Cosy self contained studio - Peak District
Indoor spacesFamilyWalkability
4.98 out of 5 average rating, 394 reviews
Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views
FamilyIndoor spacesCondition
5.0 out of 5 average rating, 285 reviews
Exclusive & Beautiful Modern Studio Flat
Indoor spacesFamilyNearby
4.82 out of 5 average rating, 272 reviews
Beautiful barn conversion.
KitchenFamilyDecor
4.99 out of 5 average rating, 177 reviews
The Kennels
KitchenIndoor spacesLayout
4.99 out of 5 average rating, 305 reviews
Springwood Cottage Private and Unique
FamilyKitchenBackyard
5.0 out of 5 average rating, 200 reviews
Dog Friendly, Cosy, Peaceful, Walks, Peak District
KitchenFamilyCondition
4.98 out of 5 average rating, 238 reviews
Slinky The Narrow Boat
Indoor spacesKitchenAmenities
4.99 out of 5 average rating, 101 reviewsFamily-friendly home rentals with a pool

The Round House - family house with indoor pool
FamilyKitchenEV charging
4.84 out of 5 average rating, 293 reviews
Boutique Retreat, Summer Pool, Peak District
FamilyKitchenView
4.95 out of 5 average rating, 417 reviews
Dog Friendly Ground Floor Cottage with Shared Pool
KitchenIndoor spacesLaundry
4.83 out of 5 average rating, 101 reviews
Swimming Pool Peak Park Cottage 15 Min Alton Tower
FamilyIndoor spacesHospitality
4.92 out of 5 average rating, 234 reviews
Luxury Shepherd's Retreat with Hot Tub
KitchenIndoor spacesNearby
4.98 out of 5 average rating, 133 reviews
Romantic Peak District Spa Cottage •Hot Tub & Pool
KitchenFamilyDecor
4.83 out of 5 average rating, 138 reviews
Dog Friendly Retreat
Indoor spacesKitchenBarbecue
4.8 out of 5 average rating, 142 reviews
Winnow Nook - romantic getaway for 2
KitchenFamilyGetting around
4.99 out of 5 average rating, 144 reviewsWhen is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $208 NZD | $233 NZD | $235 NZD | $242 NZD | $247 NZD | $250 NZD | $221 NZD | $233 NZD | $212 NZD | $212 NZD | $205 NZD | $215 NZD |
| 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
- Wythenshawe Park
- Harewood House
- Tatton Park
- University of Manchester
- Bramham Park
- Yorkshire Wildlife Park
- Bowlers Exhibition Centre
- Manchester Central Convention Complex
- Temple Newsam Park
- Yorkshire Sculpture Park
- The Piece Hall
- Mam Tor
- Belvoir Castle
- MediaCityUK





