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Condo holiday rentals in Chesterfield

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Quick stats about condo rentals in Chesterfield

  • Total holiday rentals

    Explore 10 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $154 AUD per night before taxes and fees

  • Verified guest reviews

    Over 850 verified reviews to help you choose

  • Wi-Fi availability

    10 of Chesterfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesterfield rentals

  • 4.9 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated condo rentals in Chesterfield

Guests agree: These condos are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious bedroom features deep green walls and large windows allowing abundant light. A vintage-style fireplace is complemented by a decorative mirror and a wooden dressing table. A plush bed is covered with a soft quilt, and a cozy chaise lounge adds to the room's inviting ambiance.
Condo in Wirksworth

Stylish, Opulent & Spacious 18C. Peaks apartment

With the glorious peaks walkable from your doorstep, this stunning boutique hideaway in the heart of Wirksworth next door to beautiful arthouse cinema and 2 minutes from eateries & drinking holes transports you to a time of luxury, style  & opulence. It's bespoke design, original features and decor from nationally renowned designers, Black Pop and Curiousa & Curiousa, timelessly provide all the trappings expected from a 21st century, 5 star boutique hotel but in a fascinating building from 1766.

4.98 out of 5 average rating, 323 reviews
Top Guest favourite
A cozy living room features a comfortable sofa adorned with vibrant throw pillows. Natural light streams through an arched window, highlighting the exposed stone wall. Two elegant lamps illuminate the space, complemented by a small accent table on either side.
Condo in Matlock Bath

Historic Victorian 3 Bed 4 Bath Flat ~Matlock Bath

A cosy and relaxing "home from home" stay awaits you at this centrally located Victorian property in the historic and quirky town of Matlock Bath, where you'll be greeted with breath taking views across the Derbyshire Dales. Our property comes supplied with everything from board games, books, Netflix, dvds, games console to baking equipment should the mood take you. There are several cafes, pubs and restaurants to choose from aswell as entertainment to keep you amused all in walking distance.

4.94 out of 5 average rating, 149 reviews
Guest favourite
The spacious lounge features a comfortable white sofa paired with a striped armchair and ottoman. A coffee table is positioned in front of a modern entertainment unit holding a large television. Large windows allow natural light, with sheer curtains framing the view.
Condo in Mansfield

Newly Renovated Two Bedroom Ground Floor Cosy Flat

Newly renovated, spacious and comfortable Flat. Consisting of a large comfortable lounge, with Sky TV and Broadband. Modern Kitchen with all utilities and comforts of home. Bright Bathroom with walk-in electric shower and plenty of storage. Good sized double bedroom with triple wardrobe a large single bedroom/office with door leading out to the private patio area. Less than a 5 minute walk to local supermarket, 3 pubs , Costa, Kings Mill Hospital and lake. 5 min. drive to Mansfield Centre.

4.87 out of 5 average rating, 151 reviews
Top Guest favourite
A ground floor entrance is framed by a brick exterior. Two white chairs and a small table are positioned on a stone patio, inviting relaxation. A glass sliding door offers a view into the studio, with a landscaped area visible nearby.
Condo in Chesterfield

The Studio at Lorien -Chesterfield -EV Charger

Welcome to our ground floor studio, private entrance, bathroom, kitchenette with fridge freezer, microwave, double bed, wall-mounted TV. PAYG EV Charger - Ideal for business travellers and couples seeking a relaxing break. Located on a quiet, tree-lined avenue. Minutes from Chatsworth Road's bars and restaurants. Close to the Peak District, Chatsworth House, Buxton, Bakewell, and Matlock, guest access via a coded key lock. Nestled near the Hipper Valley bike trail for a peaceful retreat.

4.98 out of 5 average rating, 198 reviews
Guest favourite
A wooden entrance door is framed by large planters filled with vibrant flowers and lush greenery. The glass panels of the door are partially frosted, allowing light to filter through. The surrounding area is adorned with hanging baskets overflowing with colorful blooms.
Condo in Dronfield

Exclusive & Beautiful Modern Studio Flat

Located on Green Lane, traffic is busy at peak times of the day, however this private studio is perfect for access to the Peak District. There is a kitchen, a spacious bathroom, pull-down double bed (only a small 4 ft double). The flat is best suited for a single person but if you are in a couple and the bed is ok, then this will suit you. The Peak district is just a short car ride away. Restaurants, supermarkets; train station and buses will take you to Sheffield or chesterfield.

4.82 out of 5 average rating, 270 reviews
Top Guest favourite
A comfortable living area features exposed wooden beams and a cozy sofa. A wooden coffee table sits in front, with a television mounted nearby. Natural light enters through a window adorned with soft blinds, creating an inviting space for relaxation.
Condo in South Wingfield

The Conkers Country Cottage Self Catering Retreat

The Conkers is in the picturesque Hamlet of Moorwood Moor on of the edge of the Peak District. There are many walks from the door and 150 yards along the lane is The White Hart Inn where you will experience good food or just enjoy a well-deserved glass of wine. The Conkers delightful garden and orchard area provides a lovely spot for a relaxing drink, or perhaps some alfresco dining after a busy day exploring. There is ample off road secure parking behind automated gates.

4.91 out of 5 average rating, 147 reviews
Top Guest favourite
A brown leather sofa is positioned in a quiet living area, complemented by a wooden coffee table featuring three decorative glass candle holders. Above the couch, three sepia-toned elephant portraits are displayed, adding a touch of character to the space.
Condo in Sheffield

Ecclesall Road! 2 bed apartment, amazing location

Hotel style feel stay at this central Ecclesall road location. The apartment comprises of 2 double bedrooms, both fitted with king size beds. Walk in shower wet room with remote controlled mood lighting. Fully integrated kitchen that flows into a relaxed living area with smart wall mounted TV, reading corner with dining table and chairs. A stone’s throw from the centre of Ecclesall road. With parks, trendy bars and flavoursome restaurants all at your doorstep!

4.94 out of 5 average rating, 433 reviews
Guest favourite
A cozy living space is showcased with a stylish leather sofa and an eye-catching egg chair nestled in the corner. Large windows reveal a view of the city at sunset, complemented by modern lighting and a textured stone accent wall.
Condo in South Yorkshire

House of Suede in the Heart of Kelham Island

UNIS Estates is pleased to present the House of Suede serviced apartment located in the heart of Sheffield’s vibrant Kelham Island. Boasting impeccable interior design, captivating selective ambience and a minimalist touch, this property offers a truly distinctive and luxurious stay. Enhance your visit by enjoying complimentary access to the on-site gym or taking a leisurely stroll to the rooftop terrace, offering breathtaking views of the Kelham surroundings.

4.85 out of 5 average rating, 193 reviews
Top Guest favourite
The exterior of the historic watermill building is shown, featuring a stone facade and large windows. A clock is positioned above the main entrance, while a blue door adds a contrasting element. Surrounding greenery and small planters enhance the entrance area.
Condo in Derbyshire

Litton Mill Retreat, Luxury Converted Mill

Nestled in the heart of the Peak District National Park, Litton Mill is a beautifully converted former watermill just minutes from the Monsal Trail. Recently renovated, the large apartment is 1,400 sqft & features a stunning open plan living, dining and kitchen space filled with natural light. Two spacious en suite bedrooms offer super king beds (or twins), each with an additional pull-out single bed, making it ideal for couples, families or groups.

4.96 out of 5 average rating, 256 reviews
Superhost
The living area features a comfortable gray sofa, accompanied by decorative cushions. A light wooden bookshelf holds various books, while a dining table adorned with a vase of roses occupies the foreground. The space is filled with natural light from nearby windows.
Condo in Chesterfield

The Corner House A-2 Bedroom Town Centre Apartment

A stylish ground-floor apartment in a beautifully converted 1800s home, recently refurbished to a high standard and exclusively used for Airbnb guests. The property features two double bedrooms, a full bathroom plus a separate toilet, and a fully equipped open-plan kitchen/diner with a sofa bed - perfect for relaxing stays. Within walking distance of Chesterfield town centre and train station, with allocated parking for one car.

4.82 out of 5 average rating, 147 reviews
Top Guest favourite
A self-contained living area is shown, featuring a spacious bed with light green bedding. A small desk holds a kettle and decorative items, accompanied by a wall-mounted TV. Soft carpeting and wainscoting in soothing green create a pleasant backdrop for relaxation.
Condo in Warsop

Fairwinds

Quiet village location, on the very edge of Sherwood Forest,self contained annex. Sherwood pines/Forest,Go ape,creswell crags,Thoresby park,clumber park,Center parks and Rufford abbey all within 4miles. Drop works Rum Distillery 3miles. 2.5miles to the nearest EMR station. 2 minutes walk to bus stop for Mansfield. Village cafe and bars within 10 minute walk. Local walks and cycle routes nearby.

4.97 out of 5 average rating, 160 reviews
Top Guest favourite
A modern stone-clad apartment building is visible, featuring several windows and a tree in the foreground. The landscaped lawn includes greenery and shrubbery, while a pathway leads to the entrance of the building. Overcast skies create a calm ambiance.
Condo in Crookes

Comfortable 2 bedroom flat in Western Sheffield

A comfortable and spacious two bedroom apartment in the quiet leafy residential area of Sheffield 10. Private parking and quick access by public transport to city centre (3.7 miles/25mins) and 5 minute drive to the scenic Peak District National Park. Handy for Sheffield University, Broomhill the Hallamshire Hospital and Thornbury private hospital. Claremont private hospital is next door.

4.99 out of 5 average rating, 155 reviews

Popular amenities for Chesterfield condo rentals

KitchenWifiFree parking on premisesAir conditioning

Weekly condo rentals

Guest favourite
A spacious living area is featured with a large grey sectional sofa adorned with colorful cushions. A wooden coffee table sits atop a plush area rug, complementing the light, airy atmosphere. Artwork and decorative elements create an inviting space for relaxation.
Condo in Bakewell

Cobblers Rest in Central Bakewell & Free Parking

4.81 out of 5 average rating, 190 reviews
Guest favourite
The exterior of an 18th-century water-powered mill is shown, featuring a stone facade and large, arched windows that offer a glimpse into the building's history. Blue doors provide contrast against the gray stone, set within a lush green landscape.
Condo in Derbyshire

Six Litton Mill | Amazing Water Mill Apartment

4.9 out of 5 average rating, 226 reviews
Guest favourite
A bright open lounge area features a comfortable settee adorned with colorful cushions. A wooden chest of drawers and a small table are present, with a flat-screen television mounted on the wall. Natural light floods in from a skylight, illuminating the space.
Condo in Matlock

The Forge, Snitterton near Matlock

4.87 out of 5 average rating, 440 reviews
Top Guest favourite
The image features a charming entrance, showcasing large glass doors framed by soft curtains. Seasonal wreaths adorn the door, complemented by hanging flower baskets. A small black mailbox is visible beside the door, while decorative plants enhance the welcoming exterior.
Condo in Matlock Bath

1 Coach House Mews - Matlock Bath

4.88 out of 5 average rating, 181 reviews
Guest favourite
An outdoor seating area features a modern gray couch and two chairs surrounding a small circular table. The space is surrounded by greenery, with trees and plants providing a serene backdrop. Natural stone flooring complements the inviting atmosphere.
Condo in Crookes

Fabulous vintage vibe - Sheffield & Peak District!

4.81 out of 5 average rating, 150 reviews
Top Guest favourite
An open-plan kitchen and dining area features a sleek white countertop with modern appliances. Rich red brick walls contrast with the contemporary cabinetry. A wooden staircase leads to the upper level. Large windows allow ample natural light to fill the space.
Condo in Edwinstowe

The Old Chapel Apartments

4.96 out of 5 average rating, 111 reviews
Guest favourite
The living area features a modern open layout with dark cabinetry and a wooden countertop in the kitchen. Comfortable armchairs and a navy sofa offer seating, complemented by a coffee table and a soft rug. Natural light enters through large windows framed by neutral walls.
Condo in Sheffield

Flat in landmark building, Castlegate, City Centre

4.94 out of 5 average rating, 202 reviews
Top Guest favourite
Condo in Sheffield

Fabulous 2 Bedroom City Centre Apartment & Balcony

4.93 out of 5 average rating, 147 reviews

Pet-friendly condo rentals

Top Guest favourite
An inviting stone exterior features a staircase leading to the entrance of the apartment. The building's rustic charm is highlighted by wooden doors and window frames. A small table with flowers adds a welcoming touch to the entrance.
Condo in Derbyshire

Fields Farm Luxury Apartment

4.98 out of 5 average rating, 292 reviews
Guest favourite
A cozy sitting area features a dark sofa adorned with white and blue striped cushions. Natural light filters through the large window with a striped valance, offering a view of the street and nearby buildings. The neighborhood includes charming architecture and greenery.
Condo in Duffield

Loft Apartment in Village centre with Free Parking

4.79 out of 5 average rating, 233 reviews
Top Guest favourite
An open-plan layout reveals a cozy bedroom with a textured white bedspread in the foreground. A rustic brick archway leads to a modern kitchen area featuring sleek cabinetry, soft lighting, and a comfortable leather sofa, enhancing the inviting atmosphere of the space.
Condo in Matlock Bath

The View is a luxury apartment with a modern twist

4.97 out of 5 average rating, 113 reviews
Guest favourite
A modern living room is displayed, featuring a comfortable leather sofa and an accent chair. Large windows allow natural light to illuminate the space, showcasing a view of the city. Decorative plants and wall art add a touch of style, complemented by a sleek television.
Condo in Sheffield

Luxurious 2-bedroom Apartment

4.92 out of 5 average rating, 130 reviews
Top Guest favourite
Condo in South Yorkshire

Peaceful Private Annex | Parking | Pet Friendly

4.98 out of 5 average rating, 187 reviews
Superhost
A bright bedroom features a spacious bed with a light duvet and decorative pillows. A bedside table is positioned on one side, with two lamps providing soft illumination. Natural light enters through a window adorned with light blue curtains, creating a serene atmosphere.
Condo in Alstonefield

Annie's Loft- Paddock Cottages

4.87 out of 5 average rating, 110 reviews
Top Guest favourite
An outdoor patio area features a light green umbrella providing shade over a circular table and two matching chairs. Stone walls add texture to the space, which is complemented by potted plants and a gravel surface, creating a calm and inviting environment.
Condo in Derbyshire

The Burrows garden flat in central Buxton

4.99 out of 5 average rating, 151 reviews
Guest favourite
The entrance to the studio apartment is framed by a large window and a decorative flower basket. A white door with glass panels provides a welcoming entry point, while the brick façade features a mix of classic and modern detailing.
Condo in Southwell

Self contained boutique studio in Southwell

4.92 out of 5 average rating, 237 reviews

Private condo rentals

Guest favourite
A view from a cozy sleeping area leads into the fully equipped kitchen. Wooden cabinetry and modern appliances can be observed, along with a washing machine. A door provides access to an outdoor space, enhancing the overall functionality of the flat.
Condo in Crookes

1 BDR apt (sleep 2+2) close to Shef Uni (+parking)

4.92 out of 5 average rating, 403 reviews
Top Guest favourite
A bright living area features a yellow sofa bed positioned near a window, allowing natural light to enter. A wooden dining table with chairs is visible, accompanied by a patterned rug. A television is mounted on a cabinet, creating a functional space for relaxation.
Condo in Sheffield

Large self contained garden apartment

4.98 out of 5 average rating, 113 reviews
Guest favourite
A lounge area features a soft grey sofa alongside a light wood dining table and black chairs. A tall floor lamp and a minimalist television stand are included. Natural light fills the space through glass doors, which lead to a small balcony, with sheer curtains softly draping.
Condo in Sheffield

Bright one bedroom apartment in Kelham Island.

4.83 out of 5 average rating, 120 reviews
Guest favourite
The living area features a large, inviting sofa arranged around a low coffee table, with a cozy poof nearby. A wall-mounted TV is visible above a mantle. Natural light floods in through a large window, enhancing the greenery from various plants throughout the space.
Condo in The Park

THE LUXÉ stunning 2 bed in the private park estate

4.9 out of 5 average rating, 283 reviews
Top Guest favourite
An open-plan living area is presented with two comfortable sofas, a coffee table, and a dining table set for two. Large windows allow natural light to illuminate the space, with views of greenery outside. A door to the entrance is visible, alongside elegant wooden stairs.
Condo in Southwell

Stunning self contained annex in Southwell

5.0 out of 5 average rating, 284 reviews
Top Guest favourite
Condo in Derbyshire

The Penthouse | High end Luxury | Central Location

5.0 out of 5 average rating, 119 reviews
Top Guest favourite
An outdoor seating area is visible, featuring a small table and two chairs surrounded by gravel and shrubs. The private entrance to the one-story lodge is seen in the background, framed by greenery along the fence. A stone path leads up to the door.
Condo in Edwinstowe

Friars Lodge, Edwinstowe

4.96 out of 5 average rating, 351 reviews
Top Guest favourite
The lounge area is equipped with a yellow sofa and a television set. A small dining table with seating for two is positioned near the light-filled windows, which overlook a green outdoor space. A plush rug adds comfort to the wooden floor.
Condo in Sheffield

Comfortable studio in central Sheffield

4.94 out of 5 average rating, 125 reviews

Destinations to explore