Vacation rentals in Chesterfield

4.92 out of 5 average rating, 296 reviews

The living room features a cozy arrangement with a soft beige sofa and armchair, adorned with floral cushions. A low coffee table sits in front of a fireplace, while patterned curtains frame a bright window. A small TV is mounted on the wall above the fireplace.

Cottage in Chesterfield

Chatsworth Cottage

Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

4.89 out of 5 average rating, 262 reviews

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

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

Apartment in Chesterfield

A spacious studio is seen, featuring a wooden double bed and a breakfast bar with stools. Comfy chairs are positioned near a large television. Soft carpeted flooring complements the pastel-colored walls, and kitchen appliances are visible in the background, providing functional living space.

4.96 out of 5 average rating, 278 reviews

Cosy studio apartment close to Peak District

Cosy,private ,self contained upstairs studio with own entrance , double bed with en suite, dual ring halogen hob ,combination microwave and oven , television with free sat ,free wifi ,integrated fridge freezer ,breakfast bar and stools . Comfy chairs to relax! On the main bus route into Chesterfield and the Peak District ,10 mins to Chatsworth,20 mins to Bakewell and lots of walks in the area. Many bars ,coffee shops and restaurants within walking distance . We look forward to meeting you.

The entrance to the home features a well-maintained path leading to a white door, flanked by decorative planters with colorful flowers. Lush greenery and shrubs enhance the welcoming atmosphere, and a charming arrangement of potted plants adds to the inviting entryway.

4.98 out of 5 average rating, 111 reviews

Home from Home with private rose garden

Modern cosy family home on the edge of the beautiful Peak District with private garden and off road parking. Newly re-furbished. Just right for visiting famous places i.e. Chatsworth House, Bakewell for a Bakewell pudding, the caves at Castleton, walking/mountain biking on the beautiful moors or just meeting up with friends or relatives. Good bus service to town centre and the famous Crooked Spire. Local shops, restaurant, take-away, chemist within easy walking distance or 2 mins by car.

Guest suite in Wingerworth

The room features two beds covered with yellow checkered bedspreads, complemented by blue towels at the foot of each. A small side table holds a chair and decor. Light enters through a nearby glass door, adding a bright touch to the cozy space.

4.95 out of 5 average rating, 292 reviews

The Garden Room

The Annexe is self contained in the garden of our home in Wingerworth. Private entrance through small conservatory . Shower room , fridge, kettle, toaster , microwave. Cereals, bread, butter and preserves provided. Close to countryside and Peak District National Park . On drive parking. Bus stops nearby to Chesterfield and Derby with links by bus/train from Chesterfield Rail Station. Good local walks and Chatsworth Estate 20 minutes drive. Excellent Pub/Restaurant 5 minutes walk away.

4.82 out of 5 average rating, 248 reviews

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.

4.99 out of 5 average rating, 129 reviews

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 Derbyshire

Chesterfield -Peak District-Chatsworth-EV Charger

Enjoy 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.

4.97 out of 5 average rating, 325 reviews

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

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

4.99 out of 5 average rating, 116 reviews

The exterior of a stone cottage is displayed against a clear blue sky. Large windows allow light to illuminate the façade, and a set of stone steps leads up to the entrance. Nearby trees provide a natural backdrop, enhancing the overall rustic charm.

Barn in Holymoorside

Charming grade II listed cottage with hot tub

Chander Hill Cottage is a stylish 3-bedroom barn conversion nestled above the village of Holymoorside, on the edge of the Peak District. This cosy cottage is a perfect base for exploring the countryside, with numerous walks from the door and two pubs just a mile away in the village. Relax in our hot tub with stunning views or warm up by the wood burning stove after a winter walk. The enclosed cottage garden has a patio where you can enjoy a BBQ in the summer. Dogs welcome!

4.98 out of 5 average rating, 344 reviews

A well-arranged bedroom features a spacious bed with decorative pillows and a cozy quilt. A window with striped blinds provides natural light and a view of greenery outside. An ice bucket and two glasses are placed on a bedside table, adding a touch of elegance.

Guest suite in Ashover

Hunger Hill Farm Studio - Derbyshire Dales

Set in the glorious Peak District in a rural and peaceful location is our lovely self contained studio. Glorious views and walks over rolling countryside. Close to Chatsworth House and Haddon Hall. With the popular wedding venue (Peak Edge Hotel ) within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here. Perfect for the Chatsworth Christmas market.

4.94 out of 5 average rating, 102 reviews

A spacious living area is presented with two comfortable sofas arranged around a coffee table. Artwork is displayed on the walls, and a large flat-screen TV is mounted. Light fixtures illuminate the room, creating a welcoming environment.

Apartment in Dronfield

The Old Bank Luxury Serviced Apartment Derbyshire

This is a 2 bedroom, recently renovated, luxury serviced apartment. We can accommodate up to 4 guests with a super comfy king sized bed with 50” smart TV, 2nd bedroom 2 single beds and 43” smart TV. There is a fully equipped dining kitchen with washer, dishwasher, oven, microwave and table / chairs for 4 people. Stunning en-suite walk in shower room refurbished to the highest standard! Full bathroom with bath and shower. We also offer discounts for stays longer than 2 nights.

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

4.83 out of 5 average rating, 137 reviews

2 Bed Apartment at the Corner House

A ground floor two double bedroom apartment in a converted 1800s home which has recently undergone further high-spec refurbishment, used solely for guests. The open plan kitchen/diner holds a sofa bed is perfect for a relaxing stay. The property is within walking distance to Chesterfield town centre and train station with an allocated parking space for one car. This is perfect for anyone commuting or working in the area as well as visiting the Peak District.

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Popular amenities for Chesterfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chesterfield

4.93 out of 5 average rating, 14 reviews

A light-filled living area features large arched windows that allow natural light to illuminate the space. A cozy sofa is paired with a sleek dining table set for four and complemented by modern seating. Decorative plants add a fresh touch to the inviting ambiance.

Condo in Derbyshire

Spire View

The exterior of the brick house is showcased, featuring a charming door with a small balcony above. Large windows allow natural light in, while the well-maintained driveway provides ample space for parking. A clear blue sky enhances the welcoming appearance of the property.

4.96 out of 5 average rating, 57 reviews

Home in Chesterfield

4.99 out of 5 average rating, 107 reviews

The exterior of the Coach House features a charming stone facade with a moss-covered roof. Two garage doors, framed by flower pots, provide a warm welcome. A gravel driveway surrounds the building, complementing the tranquil setting among mature trees.

Apartment in Harthill

The Coach House Harthill

4.97 out of 5 average rating, 38 reviews

The exterior of a two-bedroom house is presented, showcasing a brick façade with a gabled roof. A driveway leads to a black vehicle parked beside the entrance. Lush grass borders the pathway, and a clear blue sky is visible overhead.

Home in Walton

Derbyshire Gem, Peak District

5 out of 5 average rating, 18 reviews

A light-filled living area features a comfortable sectional sofa in soft gray, complemented by decorative pillows. A dark coffee table occupies the center space, while large glass doors open to a private outdoor seating area, enhancing the connection to nature.

Home in Brimington

Blissful Barry’s

Apartment in Old Whittington

A bedroom is featured with a spacious bed dressed in floral bedding. A wooden wardrobe with mirrors stands beside the bed. A bedside lamp provides soft illumination, while neatly folded towels are placed at the foot of the bed, offering a sense of comfort and convenience.

4.86 out of 5 average rating, 63 reviews

The Hideaway

Superhost

The exterior view of the property showcases a well-maintained garden with flower pots and neatly trimmed grass. A dark front door is positioned next to several window panels, allowing natural light to illuminate the entrance. The brick facade adds character to the home.

4.7 out of 5 average rating, 91 reviews

Commuters Getaway Chesterfield

A cozy living area is presented with a brown sofa adorned with decorative cushions. A wooden coffee table sits in front, complemented by a patterned area rug. A wall-mounted television and a decorative shelf enhance the space, which is warmed by a stove and illuminated by natural light.