Holiday rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

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

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Top guest favourite
A well-maintained pathway leads to a beautifully designed cottage surrounded by lush greenery. The property features manicured hedges and trees, with a clear blue sky overhead, creating a welcoming entrance to the private garden area.
Guest house in Derbyshire
4.99 out of 5 average rating, 183 reviews

Springwood Cottage Private and Unique

Springwood Cottage is ideally situated in a beautiful location on the edge of Derbyshire is completely self contained with its own entrance and private garden area with parking outside. The Cottage is completely newly built in 2020 and designed to the highest standard. Well behaved Dogs welcome, we are happy to accommodate 2 dogs, please request if you have more than 2. A deluxe super kingsized bed (6 x6 foot) with the most up to date memory foam mattress and a comfortable sofa bed in the lounge

Top guest favourite
Cottage in Chesterfield
4.92 out of 5 average rating, 318 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.

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
4.89 out of 5 average rating, 290 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
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, 206 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.

Guest favourite
A modern, light-filled living area features a gray sectional sofa adorned with colorful, geometric pillows. A simple wall-mounted shelf is visible on the left, and a front door, partially open, allows natural light to enter the space.
Townhouse in Chesterfield
4.92 out of 5 average rating, 167 reviews

Cheerful 2- Bedroomed Home in Chesterfield.

This beautiful town house is located right on the edge of the Peak District and within walking distance to 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. The locations boasts a 20 min drive to the well loved Peak District. Along with all the wonderful bars, restaurants, gift & coffee shops just a short walk away. Chesterfield's Golf course is just 15min drive away.

Top guest favourite
A stone exterior of the building is highlighted, featuring a prominent navy-blue door framed by two windows. Soft lighting enhances the entrance, surrounded by a neatly landscaped area with low shrubs and pavers leading to the door.
Cottage in Darley Dale
4.99 out of 5 average rating, 254 reviews

The Kennels

Kick off your walking boots, wash down your bike or just park up the car, this freshly converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

Top guest favourite
A charming two-story cottage is presented with a welcoming façade featuring pale pink and cream walls. A quiet street is visible alongside, with a parking space indicated. Lush trees line the road, enhancing the serene environment of the neighborhood.
Townhouse in Chesterfield
4.86 out of 5 average rating, 109 reviews

Cottage by the Park Chesterfield - Peak district

Our COTTAGE is situated with a PARK on our doorstep and 15 min drive to Baslow in the PEAK DISTRICT . Also within walking distance to Chesterfield town center and Chatsworth road. Only a 15 min walk to bars, restaurants, coffee shops, and local boutique shops on Chatsworth Road. It is a short drive to Chatsworth house, Bakewell, Matlock and many of the delightful areas in the Peak district. Our home is cozy and welcoming! We hope you will choose us for your next visit to the area.

Top guest favourite
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.
Flat in Chesterfield
4.96 out of 5 average rating, 288 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.

Top guest favourite
A kitchen window framed by white curtains offers a view of the surrounding countryside. A small vase with flowers sits on the wooden countertop, along with a bottle of wine and a round tray. Shelves above display jars and other kitchen items.
Guest suite in Holmesfield
4.97 out of 5 average rating, 100 reviews

One Bedroom Studio with full kitchen & log burner.

Located in the village of Holmesfield in Derbyshire. On the edge of the Peak District with Chatsworth House 10 minutes drive away. Sheffield is a short drive away. The accommodation comprises, kitchen and a King size bed. A sitting room with central heating and log burner, a shower, toilet & sink. Utility room with washing machine, coffee machine and breakfast bar. Stunning views of Derbyshire.Private entrance. Car parking. PLEASE NOTE: NO CHILDREN INCLUDING INFANTS UNDER TWO YEARS OF AGE.

Top guest favourite
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.
Guest suite in Wingerworth
4.94 out of 5 average rating, 325 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.

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, 342 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 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 Calow
4.95 out of 5 average rating, 337 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 outside

Popular amenities for Chesterfield holiday rentals

When is the best time to visit Chesterfield?

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Avg. price$115 SGD$116 SGD$118 SGD$127 SGD$129 SGD$129 SGD$140 SGD$152 SGD$132 SGD$143 SGD$138 SGD$140 SGD
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Frequently Asked Questions

  • Are there family-friendly house rentals in Chesterfield?

    Chesterfield has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Chesterfield?

    Experience the best of Chesterfield with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly house rentals in Chesterfield?

    Four-legged friends are welcome in Chesterfield. Choose from more than 30 house rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Chesterfield?

    Yes! Work meets play with ease at over 30 house rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Chesterfield?

    Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 200 vacation rentals in Chesterfield, and over 200 vacation rentals in Brimington.

  • Do house rentals in Chesterfield have a kitchen?

    Absolutely! We offer over 60 house rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Chesterfield have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chesterfield have free parking?

    Absolutely! We offer over 50 house rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Chesterfield

  • Total holiday rentals

    Explore 110 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 7,360 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    100 of Chesterfield holiday rentals include wifi 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!

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  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield