
House holiday rentals in Chesterfield
Find and book unique houses on Airbnb
Quick stats about house rentals in Chesterfield

Total holiday rentals
Explore 70 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 4,120 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

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 house rentals in Chesterfield
Guests agree: these houses are highly rated for location, cleanliness and more.

Beautiful Barn surrounded by open countryside
A beautiful barn conversion surrounded by open countryside within The Peak District National Park. Ideally situated for exploring the Peak District, with excellent footpath access across the moors or the Sheffield Lakeland from the door . The City is only a short drive away with all of it's amenities. There is an excellent choice of local pubs and restaurants serving great food, local beers plus for Fine Dining, we are only 10 mins away from Sheffield's only Michelin starred restaurant Joro.

The Old Coach House. 5-star. Parking. EV charger.
“Loved staying here”. Off street parking. Ultra fast WiFi. Perfectly located in leafy Nether Edge village, 10 minutes from city centre and Peak District. Near to local shops, pubs, cafés and restaurants. Everything you need for the perfect stay: Private off-street parking: Yes. Big comfortable beds: Yes. Powerful shower: Yes. Washing machine: Yes. New kitchen: Yes. Spotlessly clean: Yes. Ultra-fast 1GB fibre optic broadband/Wi-Fi: Yes. Ev charger: Yes. Charm, character, history? Yes. Yes. Yes!

Panoramic views, Spring Lambs, Bakewell Chatsworth
The Garden Nook offers complete privacy and is located in a perfect spot for everything. Newly converted and set within 55 acres of impressive private land, gardens, and fruit orchards. A rejuvenating location to unwind and reconnect with nature in such a tranquil environment. The comfy contemporary haven with tasteful decoration, stylish furniture, and spectacular views is the perfect place to relax. Watching lambs skipping around the orchard is a delightful bonus! Tractor experiences available

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

The Stables House, Lomberdale Hall. 4 to 7 guests
Spacious detached private house, 3,000 sq ft/ 275 sq m. Own drive. 3 acres of grounds. Log burner (fuel provided) Front, back and garden doors; Entrance hall, sweeping staircase, beautiful sitting room, library stuffed with books, 3 large bedrooms (Vispring beds) plus 3 fab bathrooms with baths & separate showers - plus a single bed downstairs. Warm kitchen, utility room & larder. Antique furniture, lovely curtains. Perfect for families, couples, groups. Walking galore! 3 Pubs in the village.

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 Round House - family house with indoor pool
Architect-designed The Round House sits just above the Peak District village of Rowsley, boasting stunning views towards Haddon Hall and Bakewell. Walk to Chatsworth House (3 miles) across the fields following the River Derwent. Set in 9 acres of peaceful landscaped gardens with wonderful birdlife - but only a few miles from the market town of Bakewell. Plenty of great walks from the house plus all year round indoor heated pool shared with Woodside Cottage - also at the same location.

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

Comfortable cottage on the Chatsworth Estate
Yeldwood Farm Cottage is a beautiful barn conversion on our farm, just outside Baslow. The self-catering cottage sleeps 2 guests, in a Super-King size (or Twin) master bedroom. The cottage comprises a fully equipped kitchen, dining room, sitting room and bathroom with a large bath and shower. We are ideally situated on the Chatsworth Estate within the Peak District, close to Chatsworth House itself, Haddon Hall, Bakewell, Eyam, Matlock, Castleton, Buxton and Sheffield.

Peaceful hideaway Baslow Chatsworth, Peak District
Gorse Ridge End is a fresh and airy bungalow superbly situated in the beautiful village of Baslow in the heart of the stunning Peak District National Park. Within walking distance of the Chatsworth Estate, excellent village pubs, restaurants and dramatic gritstone crags and moorlands. In a peaceful village location away from the main road with private garden and plenty of off road parking, this 2 bedroom property provides a tranquil base for a couple or a family.

Hugo’s Luxury Barn
Welcome to Hugo’s Barn!! Nestled in the heart of the Peak District, Hugo’s Barn at Knabb Farm offers a luxurious and tranquil escape for couples, families, and dog lovers alike. Surrounded by stunning countryside, it’s the perfect retreat to unwind and explore the natural beauty of the region. Located just a short drive from Bakewell, Chatsworth, Matlock, and Matlock Bath, Hugo’s Barn provides a peaceful yet accessible base for your Peak District adventure.

The Little Lodge
Kick back and relax in this calm, stylish space. The Little Lodge is a brand new renovated annex attached to a charming Victorian Lodge from the 1800s. Situated in a picturesque and peaceful conservation area on a private road in the leafy suburb of Ranmoor Sheffield. The Little Lodge is only 15minutes away from Sheffield's main train station and sits of the foothills of South Yorkshire's famous Peak District. Ideal for a city break or a Rambler's retreat.
Popular amenities for house rentals in Chesterfield
House rentals with a pool

Charming 6-Bedroom Winster Village, Peak District

Large Modern Décor 3 Bed with Driveway & Garden

Ashbourne Cottage nr Dovedale

28 Fentley Green

Haddon F'house - shared heated pool & games room

The Manor House

Badgers Wood

Country Cottage With Shared Swimming Pool
Weekly house rentals

Country Cottage with great outside space & views

Cosy house with spectacular views in Matlock

Cheerful 2-bedroom home with free offroad parking

Bridgefoot Cottage - Wild Swimming & Hot Tub

Peak District Home from Home!

Sleeps 6 | Views of Curbar Edge, near Chatsworth

Pear Tree Lodge with private HOT TUB and garden

The Perfect Romantic Bolthole
Private house rentals

Delightful Cottage in Picturesque Rural Village

Close to town, hot tub retreat!

Chert Cottage, Great Longstone, Bakewell Peak Dist

A cosy 2 bedroom family friendly living space

Beautiful home with Stunning views and log fire.

Stunning Countryside Manor — Hot Tub & Parking

Home in Chesterfield

Central Bakewell Quiet Luxury
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $151 SGD | $154 SGD | $157 SGD | $136 SGD | $130 SGD | $128 SGD | $152 SGD | $163 SGD | $147 SGD | $154 SGD | $143 SGD | $152 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
- Family-friendly rentals Chesterfield
- Cabin rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with a patio Chesterfield
- Flat rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Cottage rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- House rentals Derbyshire
- House rentals England
- House 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





