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House holiday rentals in Chesterfield

Find and book unique houses on Airbnb

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 stone barn conversion is displayed, featuring a charming entrance with a large wooden door. The exterior showcases a blend of natural stone and modern design elements. Surrounding greenery and an archway are visible in the background, enhancing the rural setting.
Home in Bradfield
4.98 out of 5 average rating, 156 reviews

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.

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, 552 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, 298 reviews

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

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, 305 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, 241 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.

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
4.91 out of 5 average rating, 109 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.

Guest favourite
An indoor heated swimming pool is framed by large wall-length windows, offering ample natural light. The pool features a curved shape with metal steps leading into the water. Lounge chairs are positioned nearby, inviting relaxation beside the serene water.
Home in Rowsley
4.84 out of 5 average rating, 276 reviews

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.

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, 346 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

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, 448 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, 261 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 Derbyshire
4.92 out of 5 average rating, 135 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.

Top guest favourite
Home in South Yorkshire
4.97 out of 5 average rating, 154 reviews

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

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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
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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!

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