
Family-friendly vacation 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.

Studio Annexe on the Edge of the Peak District
A bright and airy ground floor annexe, used solely for guests. With its own entrance, a comfortable double bed, fully equipped kitchen and outdoor patio area, you are guaranteed a relaxing and private stay. Nestled away in the village of Tupton on the edge of the Peak District, we hope that you can find a place to relax, eat and explore. If you're with us for work, moving house or to see family, then we have everything you need from pots and pans to a washing machine as well as a space to park.

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.

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.

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.

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.

Chesterfield -Peak District-Chatsworth-EV Charger
Enjoy 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.

Cosy self contained studio - Peak District
Set in the glorious Peak District in a rural and peaceful location is our lovely self contained studio. Glorious views and walks over rolling countryside. Close to Chatsworth House and Haddon Hall. With the popular wedding venue (Peak Edge Hotel ) within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here. Perfect for the Chatsworth Christmas market.

Beautiful place in the heart of Derbyshire
Beautiful outbuilding situated in the heart of Derbyshire. Outbuilding separated from main house. Shared garden with stunning views of the countryside. This property has its own private entrance and includes off road parking. We live within a quiet small estate that is situated in the heart of Derbyshire. lots of little towns ,Belper is a lovely town with river gardens and lovely boutiques for shopping. Fancy walking or bike riding why not visit matlock or the peak district

Studio with privacy and own space
The listing is for a studio/bedsit which is situated on our back garden. It has its own entrance with a double glazed door with lock. You would have your own parking space off the road and the studio is accessed up the drive and onto the garden. You will have free wifi and also full sky television in the studio. There is a shower room as well. We are situated in a quiet area not on an estate and our home is a detached bungalow on a row of detached bungalows.

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

Lizzy’s Luxury Cottage

Jack's Cottage, Curbar

Alpacas Hot Tub Fizz Peak District Dovedale Farm

Luxury Peak District Cottage with Hot Tub

Pear Tree Lodge with private HOT TUB and garden

The Granary

Lime Tree Cottage new barn convention

Charming grade II listed cottage with hot tub
Family- and pet-friendly home rentals

Victorian miners cottage - In small town centre

Pepper Cottage- pet-friendly, stylish & cosy

Holly Cottage a great place for a country break

The Hideaway, Great views, garden & location

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

The Gate House, Wetton. Great base for exploring.

Quiet hideaway in Matlock with far reaching views

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

Caravan near Tissington Trail

Luxury Peak District Home - 2 miles from Ashbourne

The Tissington Retreat, Ashbourne Heights

Two bed annex apartment

Indoor Pool, Pizza Oven, Close to Alton Towers

Cosy Woodside Cottage, indoor pool, nr Chatsworth

Loki’s Lodge@ Ashbourne Heights holiday park

Peak District Shepherds Hut
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ389 | ﺩ.ﺇ386 | ﺩ.ﺇ404 | ﺩ.ﺇ408 | ﺩ.ﺇ426 | ﺩ.ﺇ441 | ﺩ.ﺇ448 | ﺩ.ﺇ448 | ﺩ.ﺇ452 | ﺩ.ﺇ426 | ﺩ.ﺇ415 | ﺩ.ﺇ411 |
| 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 vacation rentals that are family-friendly in Chesterfield

Total vacation rentals
Explore 60 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 3,750 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Chesterfield vacation 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!
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- Peak District national park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- The Quays
- Lincoln Castle
- Harewood House
- Sundown Adventureland
- Mam Tor
- Tatton Park
- Royal Armouries Museum
- Holmfirth Vineyard
- Crucible Theatre
- The Nottinghamshire Golf & Country Club
- Science and Industry Museum
- Rufford Park Golf and Country Club
- IWM North
- Shrigley Hall Golf Course
- John Rylands Library
- Cavendish Golf Club
- Derwent Valley Mills
- Daisy Nook Country Park
- Manchester Central Library
- Bosworth Battlefield Heritage Centre