
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 $52 SGD 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!
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!

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.

The Kennels
Kick off your walking boots, wash down your bike or just park up the car, this freshly converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

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.

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.

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.

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

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.

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.

'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

Luxury Cottage Green Cottage, Peak District

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

Lizzy’s Luxury Cottage

The Willows Hut - with hot tub - Hillside Huts

Bridgefoot Cottage - Wild Swimming & Hot Tub

Luxury Country Cottage with Hot Tub

Boulder Field Cabin and Hot Tub

Cozy Couples Glamping - Private Hot Tub
Family- and pet-friendly home rentals

Exclusive & Beautiful Modern Studio Flat

Cheerful 2-bedroom home with free offroad parking

Springwood Cottage Private and Unique

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

Beautiful barn conversion.

Wasp Nest Cottage, Peak District

Washgate Lane Hut at Booth Farm

Stretton Hall Farm - The Pod 3
Family-friendly home rentals with a pool

Caravan near Tissington Trail

Boutique Retreat, Summer Pool, Peak District

The Tissington Retreat, Ashbourne Heights

Swimming Pool Peak Park Cottage 15 Min Alton Tower

Cosy Woodside Cottage, indoor pool, nr Chatsworth

Vale Pool Annex – Countryside Stay near Nottingham

Loki’s Lodge@ Ashbourne Heights holiday park

Dog Friendly Retreat
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $154 SGD | $172 SGD | $173 SGD | $143 SGD | $150 SGD | $155 SGD | $163 SGD | $172 SGD | $156 SGD | $156 SGD | $151 SGD | $159 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
- Apartment rentals Chesterfield
- House rentals Chesterfield
- Cottage rentals Chesterfield
- Rentals with a patio Chesterfield
- Cabin rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Flat 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
- Donington Park Circuit
- The Quays
- AO Arena
- Didsbury Village
- Lincoln Castle
- Harewood House
- Tatton Park
- Utilita Arena Sheffield
- Bowlers Exhibition Centre
- Yorkshire Wildlife Park
- Bramham Park
- Wythenshawe Park
- Motorpoint Arena Nottingham
- Mam Tor
- Royal Armouries Museum
- Temple Newsam Park
- Manchester Central Convention Complex
- Belvoir Castle
- University of Manchester





