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Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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

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Guest favorite
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 Derbyshire
4.94 out of 5 average rating, 159 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 favorite
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 Matlock
4.99 out of 5 average rating, 235 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.

Guest favorite
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 Derbyshire
4.87 out of 5 average rating, 106 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 favorite
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, 314 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.

Top guest favorite
Condo in Derbyshire
4.99 out of 5 average rating, 156 reviews

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.

Top guest favorite
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
4.99 out of 5 average rating, 154 reviews

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!

Top guest favorite
A serene sleeping area features a wooden bed dressed with a yellow patterned throw, complemented by fluffy towels. A cozy armchair provides additional seating. Large windows frame the view, allowing natural light to illuminate the space, while warm tones create a peaceful ambiance.
Guest suite in Derbyshire
4.98 out of 5 average rating, 222 reviews

Self-contained studio in amazing rural location

This comfortable studio with amazing views, lots of outdoor space, walks from the doorstep and pubs with good food nearby is perfect for couples looking to re-charge their batteries in a rural location. It has a well-equipped kitchen, including dishwasher, White Company linen, underfloor heating with independent controls, it's own combi-bolier for hot water, tv and wi-fi. It is on the edge of the Peak District with many local attractions, such as Chatsworth and Hardwick Hall.

Top guest favorite
Guest suite in Ashover
4.98 out of 5 average rating, 362 reviews

Cosy self contained studio - Peak District

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.

Top guest favorite
An outdoor terrace features a round white table surrounded by delicate chairs, overlooking lush greenery. Glass railings provide a clear view of the surrounding trees, creating a serene atmosphere. The sun filters gently through the leaves, enhancing the tranquil ambiance.
Home in Darley Dale
5 out of 5 average rating, 104 reviews

Spacious Scandinavian style hideaway with log fire

The property is in a delightful and secluded position on the south facing side of Darley Hillside with views over the valley. The main living area is on the upper floor, accessed directly from the driveway and car-port via a hallway leading to the master bedroom and ensuite; living room with open log fire, dining area and internal balcony access to 2-storey atrium complete with spiral staircase; cloakroom; toilet, and kitchen with tree top external terrace.

Top guest favorite
A bright and open studio space features a comfortable double bed with crisp white linens. A cozy seating area includes soft armchairs and a dining table set for four. Light wood accents and a floral wallpaper create a calming ambiance.
Apartment in Sheffield/Chesterfield
4.99 out of 5 average rating, 187 reviews

Peaceful setting, close to amenities and transport

The Milking Parlour is a single storey studio, it is in a quiet enclave composing of a farmhouse, and various renovated farm buildings making up 4 residences. We are situated about 50m from the main road and bus stops for regular direct buses to Sheffield/Chesterfield . Dronfield has a train station providing an hourly service direct to London. 1 mile from the Derbyshire countryside, 10miles - Chatsworth House, 12 miles - Bakewell.

Top guest favorite
The exterior of the cabin is illuminated by warm outdoor lighting, showcasing its wooden structure. A wooden fence surrounds the property, highlighting the cozy deck area with a clear view of the natural surroundings.
Farm stay in Derbyshire
4.98 out of 5 average rating, 169 reviews

Rita's Retreat

Rita’s Retreat is set on a working small holding, with lovely views across the fields, and sheep grazing close by. Inside is a handmade double bed, made locally, a full size shower with sink and WC and heated towel rail, well equipped kitchen, comfortable living area and Smart TV. Outside is a decking area with Bistro set and also an area with a fire pit. Not suitable for children Not suitable for pets

Top guest favorite
A modern two-story home features a clean white exterior with large windows and a circular accent window. A wooden fence offers privacy to the front yard, which displays a paved pathway leading to the entrance. The sky is partly cloudy, creating a serene backdrop.
Home in Derbyshire
4.98 out of 5 average rating, 252 reviews

'Rose House' Modern 3 Bedroom Detached House

Located a mile from Chesterfield town centre. The property consists of a large open plan lounge/kitchen, 2 double bedrooms and 1 single room with bunk beds. The garden is south facing and there is private parking. There are a range of bars, cafe's, restaurants and local amenities just a short walk from the property. Chatsworth House, Haddon Hall and Peak District are 15 minutes drive away.

Popular amenities for Chesterfield vacation rentals

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$18,819 GYDG$19,028 GYDG$19,447 GYDG$20,910 GYDG$21,119 GYDG$21,119 GYDG$23,001 GYDG$24,883 GYDG$21,747 GYDG$23,420 GYDG$22,583 GYDG$23,001 GYD
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 50 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Chesterfield?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with a kitchen, over 40 homes with free parking, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Chesterfield?

    Four-legged friends are welcome in Chesterfield. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Chesterfield?

    Chesterfield has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Chesterfield have a kitchen?

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

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

    Experience the best of Chesterfield with our condo rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chesterfield have wifi?

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

  • Where should I stay in Chesterfield?

    Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 180 vacation rentals in Chesterfield, and over 180 vacation rentals in Brimington.

Quick stats about vacation rentals in Chesterfield

  • Total vacation rentals

    Explore 110 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at G$6,273 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,360 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Chesterfield vacation 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!

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