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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Top guest favorite
A modern kitchen with sleek cabinets is complemented by a spacious living area. The kitchen features a granite countertop and is equipped with appliances. Natural light filters through a large window, illuminating the warm wood flooring and tasteful decor in the adjoining space.
Guesthouse in Derbyshire
4.99 out of 5 average rating, 189 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 favorite
A cosy living room features a woodburner set within a stone fireplace. A large mirror above reflects light, while a television is positioned beside a small table with decorative items. A comfortable sofa with patterned cushions is complemented by a vibrant area rug and a window offering a view.
Cottage in Baslow
4.95 out of 5 average rating, 327 reviews

Characterful 2 bed cottage in excellent location

A charming cottage overlooking a babbling, nature-rich brook. Full of character, this peaceful cottage boasts a cosy living room complete with woodburner, underfloor heating and exposed beams, a fabulous kitchen and a stylish bathroom. The cottage is in a superb location with top-class restaurants, the magnificent Chatsworth Estate and truly stunning local walks right on the doorstep. Bikes can be stored in the rear yard making this cottage an ideal base for foodies, cyclists and walkers alike.

Guest favorite
A paved patio area is bordered by vibrant potted plants, providing a lush view of the expansive garden. Sunlight casts gentle shadows, highlighting a comfortable seating arrangement designed for outdoor relaxation. In the distance, a greenhouse is visible amidst the greenery.
Home in Wingerworth
4.87 out of 5 average rating, 303 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 favorite
The exterior of a charming stone cottage is displayed, featuring a slate roof and multiple windows. Lush greenery surrounds the building, with planters filled with flowers placed strategically along the path, suggesting a welcoming atmosphere. A small balcony is visible on the upper level.
Cottage in Ashover
4.99 out of 5 average rating, 206 reviews

2 En-suite rural luxury cottage Ashover Derbyshire

Rural luxury 2 bedroomed en-suite cottage with kingsize bed & twin or superking. Both bedrooms have en-suite facilities one with walk in rain shower and twin with shower over bath. Ideally situated for the Peak District, Bakewell, & Chatsworth. Underfloor heating throughout and looks out onto its own woodland with picnic bench plus 2 more seating areas ideal for 2 couples. BBQ & table & chairs with cushions. Perfect for chilling out with views and walks from the doorstep. Pub 10 minute walk.

Top guest favorite
Tower in Bolsover
5 out of 5 average rating, 221 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 favorite
Townhouse in Chesterfield
4.92 out of 5 average rating, 179 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, 271 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.

Superhost
A wooden hot tub is positioned on a stone patio, surrounded by lush greenery and flower beds. Warm light from string lights enhances the serene ambiance, while the sun sets in the background, casting a gentle glow across the scene.
Cottage in Derbyshire
4.91 out of 5 average rating, 267 reviews

Lizzy’s Luxury Cottage

Welcome to Lizzy’s Cottage! Nestled in the heart of the Peak District, Lizzy’s Cottage offers a luxurious escape for couples and families. Surrounded by breathtaking countryside, the cottage provides a peaceful retreat, while being just a short drive from popular destinations such as Bakewell, Chatsworth, Matlock, and Matlock Bath. At Knabb Farm, we offer private parking for all guests, and our 7 acres of private land provide plenty of space to explore and enjoy the stunning surroundings.

Top guest favorite
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
4.99 out of 5 average rating, 182 reviews

Chesterfield -Peak District-Chatsworth-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.

Guest favorite
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

Top guest favorite
Stone steps lead through lush greenery towards the entrance of a rustic building. A serene view of the landscape is visible in the background under a clear blue sky, inviting a sense of peace and connection to nature.
Guest suite in Ashover
4.97 out of 5 average rating, 239 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
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 Chesterfield
4.98 out of 5 average rating, 262 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$22,803 GYDG$23,012 GYDG$24,477 GYDG$20,920 GYDG$21,129 GYDG$21,129 GYDG$23,012 GYDG$24,895 GYDG$21,757 GYDG$23,431 GYDG$22,594 GYDG$23,012 GYD
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Chesterfield?

    Chesterfield has more than 70 family-friendly stays. 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 vacation rentals in Chesterfield?

    Four-legged friends are welcome in Chesterfield. Choose from more than 50 vacation rentals for guests traveling with pets.

  • 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.

  • 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 apartment rentals in Chesterfield have a kitchen?

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

  • Do apartment rentals in Chesterfield have wifi?

    Absolutely! We offer over 10 apartment 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 vacation rentals in Chesterfield

  • Total vacation rentals

    Explore 120 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,680 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Chesterfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

  • 4.8 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!

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