
Family-friendly vacation rentals in Chesterfield
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Chesterfield

Total vacation rentals
Explore 70 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 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!
Top-rated family-friendly rentals in Chesterfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

The Tower
The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

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

Woolley Lodge Farm Retreat
A brand new fully furnished wooden lodge situated within the grounds of a working farm, with views across open countryside. The cabin has been furnished to a high standard and includes a double bedroom with double bed. The kitchen has a full size fridge with small freezer, full size oven and a microwave. It has a small bathroom with a full size corner shower. It has its own entrance, parking and a beautiful decked area and fire pit and BBQ . Not suitable for children or pets

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.

'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.

Lovely apartment above cafe near Peak District
The apartment is situated above the 200 year old cafe . Completely self contained with your own entrance . Barlow is a picturesque village on the very edge of the Peak District, with two great gastro pubs, one right next door . Barlow is a 10 minute scenic drive from chatsworth house . The apartment is a perfect stylish space for a perfect getaway for two .
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Close to town, hot tub retreat!

Lizzy’s Luxury Cottage

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

The Willows Hut - with hot tub - Hillside Huts

Bridgefoot Cottage - Wild Swimming & Hot Tub

Luxury Country Cottage with Hot Tub

Cozy Couples Glamping - Private Hot Tub

The Granary
Family- and pet-friendly home rentals

Exclusive & Beautiful Modern Studio Flat

Cheerful 2-bedroom home with free offroad parking

Springwood Cottage Private and Unique

Characterful 2 bed cottage in excellent location

OSLO Tiny House

Fox Cottage, 1 bedroom guesthouse in Sheffield

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

Beautiful barn conversion.
Family-friendly home rentals with a pool

Boutique Retreat, Summer Pool, Peak District

The Tissington Retreat, Ashbourne Heights

Hot Tub Indoor Pool Peak Park 15 mins Alton Towers

Grove Farm Cottage

Luxury static Peak District Heated Pool Playpark

Cosy Woodside Cottage, indoor pool, nr Chatsworth

Gorgeous Barn with Hot Tub and Games Room

Vale Pool Annex – Countryside Stay near Nottingham
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 437 | ﺩ.ﺇ 488 | ﺩ.ﺇ 492 | ﺩ.ﺇ 408 | ﺩ.ﺇ 426 | ﺩ.ﺇ 441 | ﺩ.ﺇ 463 | ﺩ.ﺇ 488 | ﺩ.ﺇ 444 | ﺩ.ﺇ 444 | ﺩ.ﺇ 430 | ﺩ.ﺇ 452 |
| 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
- House rentals Chesterfield
- Cottage rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- Apartment rentals Chesterfield
- Rentals with a washer and dryer Chesterfield
- Cabin rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a patio Chesterfield
- Condo 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
- Didsbury Village
- Lincoln Castle
- AO Arena
- Harewood House
- Tatton Park
- Bowlers Exhibition Centre
- Yorkshire Wildlife Park
- Bramham Park
- Manchester Central Convention Complex
- University of Manchester
- Mam Tor
- Temple Newsam Park
- Belvoir Castle
- Royal Armouries Museum
- Motorpoint Arena Nottingham
- The Piece Hall
- University of Leeds





