
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.

Dog Friendly, Cosy, Peaceful, Walks, Peak District
The Spinney is our super dog-friendly ground floor self-catering accommodation! We've designed it so that you & your dog have a great holiday! Part of a traditional stone barn conversion located in the Peak District & Derbyshire Dales, the Spinney offers space as well as the comfort of modern living. With cosy underfloor heating throughout, and everything you need for you and your furry friend, we are sure you will have a great time here! Peaceful setting, close to popular visitor attractions!

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

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-bedroom home with free offroad parking
Explore all the peaks has to offer with this beautifully renovated field barn. Free offroad parking, garden area. Two bedrooms, two bathrooms. Open plan downstairs gives a airy homely feel. Within easy access of footpaths and trails close to the famous quarries of derbyshire dollermite and limestone. Secluded location yet within easy reach of Wirksworth the nearest town just 5 minutes away and the beautiful village of carsington just over the hill. 2.3m Wirksworth 5.8m Matlock 1.6m Carsington

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.

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

Self-contained studio in amazing rural location
This comfortable studio with amazing views, lots of outdoor space, walks from the doorstep and pubs with good food nearby is perfect for couples looking to re-charge their batteries in a rural location. It has a well-equipped kitchen, including dishwasher, White Company linen, underfloor heating with independent controls, it's own combi-bolier for hot water, tv and wi-fi. It is on the edge of the Peak District with many local attractions, such as Chatsworth and Hardwick Hall.

The Old Bank Luxury Serviced Apartment Derbyshire
This is a 2 bedroom, recently renovated, luxury serviced apartment. We can accommodate up to 4 guests with a super comfy king sized bed with 50” smart TV, 2nd bedroom 2 single beds and 43” smart TV. There is a fully equipped dining kitchen with washer, dishwasher, oven, microwave and table / chairs for 4 people. Stunning en-suite walk in shower room refurbished to the highest standard! Full bathroom with bath and shower. We also offer discounts for stays longer than 2 nights.

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.

Rita's Retreat
Rita’s Retreat is set on a working small holding, with lovely views across the fields, and sheep grazing close by. Inside is a handmade double bed, made locally, a full size shower with sink and WC and heated towel rail, well equipped kitchen, comfortable living area and Smart TV. Outside is a decking area with Bistro set and also an area with a fire pit. Not suitable for children Not suitable for pets

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

Clover Cottage - Hot tub, Sauna & Beautiful Views

Close to town, hot tub retreat!

Holly House - Quiet Retreat

Lizzy’s Luxury Cottage

The Willows Hut - with hot tub - Hillside Huts

Luxury Country Cottage with Hot Tub

Boulder Field Cabin and Hot Tub

Pear Tree Lodge with private HOT TUB and garden
Family- and pet-friendly home rentals

Cosy studio apartment close to Peak District

Beautiful two bed cottage, with character & charm

Characterful 2 bed cottage in excellent location

Cosy luxury glamping pod Rosina.

25 The Meadows

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

Quiet hideaway in Matlock with far reaching views

Cottage retreat minutes from Chatsworth Estate
Family-friendly home rentals with a pool

Luxury Peak District Home - 2 miles from Ashbourne

Indoor Pool Peak Park Cottage 15 Mins Alton Towers

Cosy Woodside Cottage, indoor pool, nr Chatsworth

Lake Cottage -Peaceful relaxing Venue.

Vale Pool Annex – Countryside Stay near Nottingham

Loki’s Lodge@ Ashbourne Heights holiday park

Dog Friendly Retreat

Countryside Retreat with pool Secure parking
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £89 | £100 | £101 | £83 | £87 | £90 | £95 | £100 | £91 | £91 | £88 | £92 |
| 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 70 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 4,260 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
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!
Destinations to explore
- House rentals Chesterfield
- Apartment rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a patio Chesterfield
- Cottage rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with outdoor seating Chesterfield
- Pet-friendly rentals Chesterfield
- Flat rentals Chesterfield
- Cabin rentals Chesterfield
- Family-friendly rentals Derbyshire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- Peak District National Park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- Heaton Park
- The Quays
- Donington Park Circuit
- AO Arena
- Didsbury Village
- Lincoln Castle
- Harewood House
- Tatton Park
- Utilita Arena Sheffield
- Motorpoint Arena Nottingham
- Yorkshire Wildlife Park
- Bramham Park
- Bowlers Exhibition Centre
- Wythenshawe Park
- Mam Tor
- Royal Armouries Museum
- Temple Newsam Park
- Manchester Central Convention Complex
- Belvoir Castle
- The Piece Hall





