
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.

Panoramic views, April lambing, Nr Bakewell
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

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.

Country Cottage with great outside space & views
Relax in our stunning two-bedroom slice of Derbyshire heaven! Amazing walks and local pubs >1 mile away. Large terrace with fabulous views over the valley & a range of seating. 2 double bedrooms, 1 ensuite & large family bathroom. Significant renovations recently & has a highly specified kitchen inc. range. Log burner in living room & Smart TVs in Kitchen, Living room & main bedroom. WIFI & office to keep in touch with work whilst relaxing in comfort & style.

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.

Spacious Scandinavian style hideaway with log fire
The property is in a delightful and secluded position on the south facing side of Darley Hillside with views over the valley. The main living area is on the upper floor, accessed directly from the driveway and car-port via a hallway leading to the master bedroom and ensuite; living room with open log fire, dining area and internal balcony access to 2-storey atrium complete with spiral staircase; cloakroom; toilet, and kitchen with tree top external terrace.

Exclusive Detached Retreat+Games Room M1J35 1.5m
A unique duplex property that has a fully furnished games room complete with snooker table, professional air hockey table, surround sound cinema system with a self contained upstairs living space equipped to a high standard. Located in the heart of Ecclesfield you are a short distance from local amenities, woodland walks, pubs and cafes but also only a short distance to the vibrant nightlife in Sheffield. .
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

28 Fentley Green

The Farmhouse

The Manor House

Badgers Wood

Buttercup Down - shared heated pool & games room
Weekly house rentals

Quirky Peaceful Peak District Cottage 360 view

Cosy house with spectacular views in Matlock

Bridge Cottage, Castleton in the Peak District

"The Barn” at Stoop Farm

Pear Tree Lodge with private HOT TUB and garden

Luxury cottage in the Peak District National Park

The Old Timber Store - tiny home in a village

Beautiful 19th-Century Terraced Cottage
Private house rentals

On the edge of the Peak district

Beautiful 4 bed at Gateway to the Peak District

A cosy 2 bedroom family friendly living space

Cosy 2 bed home CHESTERFIELD

Home in Chesterfield

Charming 18th century stone cottage

Charming Detached Chapel with Stunning Views

Derbyshire Gem, Peak District
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 | $130 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
- Alton Towers
- Etihad Stadium
- Chatsworth House
- AO Arena
- The Quays
- Manchester Central Convention Complex
- Motorpoint Arena Nottingham
- Heaton Park
- Lincoln Castle
- Victoria Warehouse
- Harewood House
- Mam Tor
- Tatton Park
- Didsbury Village
- Royal Armouries Museum
- Utilita Arena Sheffield
- Donington Park Circuit
- The Piece Hall
- Crucible Theatre
- Wythenshawe Park
- Temple Newsam Park
- Manchester Central Library
- Science and Industry Museum




