Vacation rentals in Chesterfield District

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Top-rated vacation rentals in Chesterfield District

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Top guest favorite
Cottage in Chesterfield
4.93 out of 5 average rating, 331 reviews

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.

Top guest favorite
Bungalow in Brimington
4.93 out of 5 average rating, 14 reviews

Roundhouse View

Modern and comfortable 2-bedroom bungalow in a quiet area of Chesterfield. Ideal for professionals, relocations and short stays. Sleeps 3-4 with a double and flexible twin setup. Includes superfast WiFi, fully equipped kitchen, washing machine, free parking and a private enclosed garden. Well located for the M1, town centre and the Peak District. Dog-friendly on request. Discounts for longer stays. Easy self check-in and reliable host support. Ideal for quiet stays, fast access and easy parking

Top guest favorite
The Tower emerges from a lush green landscape, surrounded by tall trees and manicured grass. The building's robust concrete structure is accented by its original window designs, reflecting the natural beauty of the outdoors in a tranquil setting.
Tower in Bolsover
5 out of 5 average rating, 229 reviews

The Tower

The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

Top guest favorite
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, 110 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 favorite
Home in Chesterfield
4.94 out of 5 average rating, 31 reviews

Charming 18th century stone cottage

Tucked away in a peaceful corner of Newbold Village, within its own private courtyard, Carpenters Mews is a beautifully restored circa-1800 cottage. Full of character and charm, it has been thoughtfully furnished throughout. Whether you’re visiting for business, leisure, or a countryside getaway to the nearby stunning Peak District, this delightful two-bedroom home is a perfect base. It is close to all local amenities, providing everything you need for an enjoyable and comfortable stay.

Guest favorite
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
4.92 out of 5 average rating, 37 reviews

Blissful Barry’s

A quiet detached house on a cul-de-sac on the edge of the Peak District. A short stroll from pubs and an India restaurant. 10 mins walk to the chesterfield canal, only 10 mins into the town centre by car with the famous crooked spire. The house has 2 double bedrooms both with a double bed and a single bedroom with a full sized raised single bed. Matlock and Bakewell is about a 30 minute drive and both lovely places to visit. Beds are made up for arrival with linen and towels included

Top guest favorite
Houseboat in Brimington
4.99 out of 5 average rating, 80 reviews

Slinky The Narrow Boat

Slinky The Narrow Boat - Is a repurposed narrow boat that has been fixed into a set location near Dixon Lock Chesterfield, where you can enjoy all the the outdoors has to offer along with all the amenities you would want from a stay away. Slinky has a log burner for those cosy colder nights along with full working Kitchen, ensuite bathroom and a cosy double bed. Dogs are welcome to stay as Slinky is situated in its own private garden with patio overlooking the Chesterfield Canal.

Superhost
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.
Apartment in Chesterfield
4.86 out of 5 average rating, 93 reviews

The Hideaway

Surround yourself with style in this standout space. Modern recently refurbished basement apartment with private secure drive. It comprises of 1 bedroom with king size bed, kitchen/lounge with pull out sofa bed that sleeps 2. The kitchen is equipped with microwave, fridge, air fryer, kettle, toaster, Sandwich maker and all utensils. Includes all bedding and towels. Shower room. 10 min walk to the chesterfield canal. Shops, pubs and restaurants are all within walking distance.

Guest favorite
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

Guest favorite
A wooden lodge is illuminated by warm light in the evening dusk, surrounded by a wooden fence. Softly glowing string lights outline the perimeter, while purple flowers are visibly present in the foreground, adding a pop of color to the serene scene.
Farm stay in Derbyshire
4.94 out of 5 average rating, 366 reviews

Woolley Lodge Farm Retreat

A brand new fully furnished wooden lodge situated within the grounds of a working farm, with views across open countryside. The cabin has been furnished to a high standard and includes a double bedroom with double bed. The kitchen has a full size fridge with small freezer, full size oven and a microwave. It has a small bathroom with a full size corner shower. It has its own entrance, parking and a beautiful decked area and fire pit and BBQ . Not suitable for children or pets

Guest favorite
This studio apartment features a comfortable double bed with fresh linens, situated next to wooden shelving displaying decorative items. A round area rug adds warmth to the wooden floor. A cozy seating area and dining space are included, enhancing the living environment.
Apartment in Chesterfield
4.78 out of 5 average rating, 41 reviews

The Blossoms - Studio Apartment

Welcome to our newly renovated apartment in the centre of Chesterfield, where you will be able to relax in style. Modern but full of character, the The Blossoms is a bright and spacious studio on the ground with an open plan bedroom, dining space, kitchenette, and bathroom. Great for anyone commuting or working in the area or visiting the Peak District with a short walk to the train station and town centre. Paid parking from £3.80/24h and on street parking available nearby.

Superhost
A warm living space is depicted, featuring a beige sofa and a brown recliner chair. A cozy fireplace is visible, with a small dining table in the foreground. Wall decorations include heart-shaped ornaments, and a staircase leads to the upper level.
Home in Chesterfield
4.74 out of 5 average rating, 353 reviews

A cosy 2 bedroom family friendly living space

Bring the whole family to this great place, ideal for the Peak District walking. Our 2 bedroom 1 bathroom and living space has a real country cosy feel, WiFi. Free off road parking is available •. Please note before booking our cottage, there is no kitchen at the cottage ,in the living area there is a small fridge toaster kettle coffee machine microwave cutlery plates cups and glasses everything you will need for a comfortable stay

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