Some info has been automatically translated. Show original language

House holiday rentals in Chesterfield

Find and book unique houses on Airbnb

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!

Top-rated house rentals in Chesterfield

Guests agree: these houses are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
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
Home in Rowsley
4.98 out of 5 average rating, 294 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
The exterior of the stone cottage is featured, showcasing its classic design with multiple windows and a welcoming entrance. Hanging flower baskets add a touch of greenery, while the surrounding landscape displays lush grassland and rolling hills in the distance.
Home in Derbyshire
4.85 out of 5 average rating, 396 reviews

Runner Duck Cottage

A bright and airy cottage, comprising of two open plan rooms, a separate shower/WC. The kitchen area is equipped with hob, oven, fridge & microwave. In the downstairs lounge area there is a double pull out sofa bed, TV /DVD. Upstairs there is a king size bed & adjoining shower room/WC. Gas central heating. All bed linen, towels, and a welcome pack are provided. A charming little cottage for up to 4 people. Well behaved dogs are welcome. Immediate access to miles of footpaths & stunning views.

Top guest favourite
A spacious living area features two black leather sofas facing a central coffee table. A large smart TV is mounted on the wall, displaying a colorful landscape, while soft lighting highlights the textured wall panels. Two light-colored armchairs complement the seating arrangement.
Home in Catcliffe
4.98 out of 5 average rating, 112 reviews

Sheffield Charming Detached 4bd Home

Welcome to our modern, spacious home, designed to provide a comfortable and memorable stay. Whether traveling with family, friends, or for work, you'll find everything you need for a relaxing visit. Amenities You'll Love: - Effortless self check-in with a secure digital lock - Fiber-optic WiFi – ideal for work or streaming shows. - Fully stocked essentials – tea, coffee, shampoo, body wash, conditioner, towels. - Equipped kitchen including– cookware, utensils, a 5-hob cooker, and dishwasher

Top guest favourite
A charming stone cottage is framed by lush greenery, featuring multiple windows and a wooden deck extending towards a garden area. The natural light enhances the serene atmosphere of the surroundings, while the stone walls provide a rustic appeal.
Home in Butterton
4.98 out of 5 average rating, 258 reviews

Delightful Cottage in Picturesque Rural Village

Dalemore is a very special place overlooking the cobbled ford in the hidden Peak District village of Butterton. It is set in its own grounds and is within walking distance of the award-winning Black Lion Inn. Accommodating up to 6 with 2 bedrooms, 2 bathrooms and a double sofa bed, a well-equipped kitchen, wood burner for cosy nights in and dining opening onto the brook-side terrace, it provides the perfect Peak Park getaway. Make the most of your weekend with 4pm Sunday checkout on request.

Guest favourite
The renovated stone barn features a tidy exterior with a porch and flower beds filled with colorful plants. A gravel driveway leads to the entrance, and a spacious lawn area is visible. The surrounding hills create a serene countryside backdrop.
Home in Derbyshire
4.9 out of 5 average rating, 190 reviews

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

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, 108 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
The entrance to the cottage features a classic stone facade, complemented by a wall-mounted trellis and a decorative lantern. A wooden bench sits nearby, offering a place to relax. On the right, a wooden gate leads to a scenic view of the surrounding countryside.
Home in Rowsley
4.86 out of 5 average rating, 326 reviews

Beautiful 19th-Century Terraced Cottage

Meadow View is a 19th-Century Terraced Cottage, overlooking the historic village of Rowsley. Rowsley is a small village next to the Chatsworth Estate, which is home to the Duke and Duchess of Devonshire. Historic attractions include Caldwell's Mill, Haddon Hall and Peak Rail. Other activities on the doorstep include shops, pubs, restaurants and fishing. Peak Village is a 5 minute walk away and Rowsley is only a 10 min drive from Matlock and Bakewell accessible by a local bus service.

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, 347 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
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, 257 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.

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.

Top guest favourite
The exterior of a refurbished barn features a stone façade with a mix of dark and light stones. Windows are adorned with wooden frames, while a red door provides an inviting entrance. A small sign is visible beside the door.
Home in Penistone
4.97 out of 5 average rating, 151 reviews

Hidden beauty

A beutiful refurbished part of an old barn. it comprises old with the new. comfortable and spacious with underfloor heating downstairs and super fast broadband. Nearby are 2 local pubs walking distance. Also easy access to the trans Pennines trail. The village is located next to the strines with numerous walks. And plenty of surrounding villages with all amenities. Ideal for a romantic weekend away, walkers, or business people.

Popular amenities for house rentals in Chesterfield

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$150 SGD$153 SGD$157 SGD$135 SGD$130 SGD$127 SGD$151 SGD$162 SGD$146 SGD$153 SGD$142 SGD$151 SGD
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C
  1. Airbnb
  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield
  6. House rentals