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

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, April lambing, Nr 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 Entire Coach House at Middleton Hall
Relax in this peaceful unique country home, either warm yourself by the wood burner or relax out in the garden, taking in the beautiful surroundings of the private Middleton Hall estate. The Coach House has been refurbished , with designer furniture, wall paper, hand painted murals on the walls, marble shower room, hypnos beds and an American fridge freezer. The attractions are wildlife, walking and cycling. Also visiting stately houses like Chatsworth and Haddon. coach-house-middleton.

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

Bridgefoot Cottage - Wild Swimming & Hot Tub
Bridgefoot is a beautiful 17th century cottage situated in the Peak District. Guests have full use of the property including a modern, fully equipped kitchen, perfect for entertaining. There is also an exceptionally comfy and cosy sitting room, equipped with 2 sofas (one of which is a double sofa bed) a log burner and a Smart TV. The master bedroom boasts a luxurious four poster bed and an ensuite bathroom. Next door is a spacious second bedroom with two comfortable single beds.

Cuckoostone Barn - simply stunning!!
Cuckoostone Barn is a stunning property set in the White Peak area of the Peak District. The area is surrounded by nature and the perfect location to sit and watch the wildlife go by, whilst being mesmerised by the uninterrupted views of rolling countryside. Cuckoostone Barn is an excellent base to explore the wonders of the Peak District National Park, with amazing walks and cycle routes on the doorstep, or a place to simply relax and unwind in an idyllic part of the world .

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.
Popular amenities for house rentals in Chesterfield
House rentals with a pool

Large Modern Décor 3 Bed with Driveway & Garden

Ashbourne Cottage near Dovedale

6 cottages, 46 guests

The Manor House

Badgers Wood

Buttercup Down - shared heated pool & games room

Bramble

Pippinwell
Weekly house rentals

A chic retreat in the Peaks

Chert Cottage, Great Longstone, Bakewell Peak Dist

Cosy house with spectacular views in Matlock

Highfield House - Rural Retreat Derbyshire

Peak District Home from Home!

Cosy cottage, stunning views near Chatsworth

"The Barn” at Stoop Farm

The Perfect Romantic Bolthole
Private house rentals

On the edge of the Peak district

The Cottage - Derbyshire

A cosy 2 bedroom family friendly living space

Home in Chesterfield

Charming 18th century stone cottage

Derbyshire Gem, Peak District

Luxury Edge of Peak District Home

10%OFF|7DaySpecial|Student|WiFi|Parking|Sleeps12
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $122 SGD | $123 SGD | $122 SGD | $135 SGD | $129 SGD | $127 SGD | $151 SGD | $162 SGD | $146 SGD | $153 SGD | $142 SGD | $151 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 |
Quick stats about house rentals in Chesterfield

Total holiday rentals
Explore 60 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 3,940 verified reviews to help you choose

Family-friendly holiday rentals
40 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
60 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!
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- Peak District National Park
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- Chatsworth House
- AO Arena
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