
House holiday rentals in Chesterfield
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Top-rated house rentals in Chesterfield
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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.

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.

Cheerful 2-bedroom home with free offroad parking
Explore all the peaks has to offer with this beautifully renovated field barn. Free offroad parking, garden area. Two bedrooms, two bathrooms. Open plan downstairs gives a airy homely feel. Within easy access of footpaths and trails close to the famous quarries of derbyshire dollermite and limestone. Secluded location yet within easy reach of Wirksworth the nearest town just 5 minutes away and the beautiful village of carsington just over the hill. 2.3m Wirksworth 5.8m Matlock 1.6m Carsington

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 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.

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.

Pear Tree Lodge with private HOT TUB and garden
Pear Tree Lodge (with private HOT TUB & south facing garden) is a private and cosy retreat in peaceful surroundings within Henry's Orchard. Your space is across two floors housing open dining, living and kitchen downstairs with KING SIZE BED and ensuite upstairs. Located close to many woodland walks, historical waypoints, pubs, amenities, attractions and transport links in and around Yorkshire and Derbyshire.
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 near Dovedale

The Farmhouse

Haddon F'house - shared heated pool & games room

The Manor House

Badgers Wood

Country Cottage With Shared Swimming Pool
Weekly house rentals

Cozy Quiet Cottage In Pilsley

Willow Cottage Newly renovated quaint cottage

Cosy hillside cottage with logburner and projector

Cosy 2 bed home CHESTERFIELD

Stunning Countryside Manor — Hot Tub & Parking

"The Barn” at Stoop Farm

Charming 2 Bedroom Cottage in the Peak District

Central Bakewell Quiet Luxury
Private house rentals

On the edge of the Peak district

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

Blissful Barry’s

Cosy Bowness House welcomes you.
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $149 SGD | $152 SGD | $156 SGD | $134 SGD | $129 SGD | $126 SGD | $151 SGD | $161 SGD | $146 SGD | $152 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 70 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 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!
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