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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.

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Top guest favourite
A bright upstairs bedroom features a super-king size bed with a patterned duvet and cotton bedding. A large window offers views of greenery. A cozy window seat is complemented by nearby built-in storage filled with books, enhancing the spacious feel of the room.
Home in Nether Edge
4.93 out of 5 average rating, 544 reviews

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!

Top guest favourite
Home in Rowsley
4.98 out of 5 average rating, 281 reviews

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

Guest favourite
A spacious garden area is visible, featuring a variety of colorful flowers in pots, including bright yellow and pink blooms. A well-maintained lawn extends into the distance, accompanied by tree line and greenery. A soft play structure and garden shed are also included in the scene.
Home in Wingerworth
4.88 out of 5 average rating, 286 reviews

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

Top guest favourite
A spacious detached house is surrounded by lush greenery and landscaped grounds. The exterior features a stone facade, slate roof, and charming gardens with flowering plants. Free-roaming chickens are visible, adding a rural charm to the serene setting under a clear blue sky.
Home in Youlgreave
5 out of 5 average rating, 231 reviews

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.

Top guest favourite
An inviting living space is featured, showcasing a modern dining table and chairs alongside a vibrant red sideboard. A cozy armchair and a striped lounge chair add comfort, while softly illuminated pendant lights enhance the room's ambiance. Natural light filters through a window adorned with gray curtains.
Home in Chesterfield
4.9 out of 5 average rating, 105 reviews

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.

Top guest favourite
A charming stone exterior of the Coach House is highlighted, featuring a large arched entrance and a row of windows. The surrounding trees and blue sky create a serene environment, while the pathway leading to the entrance is flanked by stone walls and greenery.
Home in Bakewell
5 out of 5 average rating, 142 reviews

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.

Guest favourite
A comfortable living area is furnished with a gray sectional sofa and two leather armchairs. A glass coffee table is positioned centrally, and a wooden cabinet stands against the wall, adding storage space. Double doors lead to the outside, allowing natural light to enter.
Home in Chesterfield
4.96 out of 5 average rating, 342 reviews

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

Guest favourite
A view from a bridge showcases a serene countryside scene with a stone cottage nestled among lush greenery. The vibrant leaves of trees frame the picturesque surroundings, while the calm waters of the river reflect the natural beauty. The distant hills provide a backdrop.
Home in Froggatt
4.88 out of 5 average rating, 270 reviews

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.

Top guest favourite
A rustic barn is set against a backdrop of rolling hills and expansive skies. The stone exterior is framed by greenery, with lush grass and a distant stone wall visible. Soft clouds drift above, creating a serene atmosphere in the rural landscape.
Home in Longnor
5 out of 5 average rating, 276 reviews

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 .

Top guest favourite
A spacious bedroom features a large, comfortable bed dressed in pristine white linens. Two nightstands with lamps are positioned on either side, offering gentle illumination. A wardrobe is visible, and the soft beige walls create a calming environment.
Home in Baslow
4.94 out of 5 average rating, 433 reviews

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.

Top guest favourite
An open-plan living space is presented, featuring a cozy seating area with a blue sofa and armchair. A round dining table for four is set against the wall, while natural light enters through the doorway leading to the garden.
Home in Baslow
4.98 out of 5 average rating, 247 reviews

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.

Guest favourite
A charming stone barn exterior is framed by lush greenery. The building features several windows and is adorned with climbing vines and red leaves, creating a natural connection with its surroundings. A stone pathway leads to the entrance, enhancing the inviting appearance.
Home in Darley Dale
4.95 out of 5 average rating, 111 reviews

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

When is the best time to visit Chesterfield?

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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
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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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