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House holiday rentals in Chesterfield

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Top-rated house rentals in Chesterfield

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

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Top guest favourite
Home in Rowsley
4.98 out of 5 average rating, 281 reviews

Panoramic views, April lambing, Nr Bakewell

The Garden Nook offers complete privacy and is located in a perfect spot for everything. Newly converted and set within 55 acres of impressive private land, gardens, and fruit orchards. A rejuvenating location to unwind and reconnect with nature in such a tranquil environment. The comfy contemporary haven with tasteful decoration, stylish furniture, and spectacular views is the perfect place to relax. Watching lambs skipping around the orchard is a delightful bonus! Tractor experiences available

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
4.88 out of 5 average rating, 285 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 image presents a modern kitchen featuring sleek cabinetry and essential appliances. A cozy lounge area with neutral tones showcases a comfortable seating arrangement and a television. The spacious bedroom boasts a wooden bed frame and soft linens. A stylish bathroom includes a bathtub and waterfall shower. A scenic walking trail bordered by trees is depicted in the last image.
Home in Pilsley
4.93 out of 5 average rating, 149 reviews

Cozy Quiet Cottage In Pilsley

A beautiful, refurbished, one bedroomed cottage in a peaceful small village location, just a couple of minutes walk onto the Five Pits Trail and other great walks, yet still in close proximity to local amenities. The perfect place to enjoy a home from home getaway; self check in, full kitchen, glorious large bathroom space with bath and waterfall shower, comfy lounge area with large TV, extremely spacious cosy king bedroom and front and rear enclosed patio areas for your four legged friends!

Top guest favourite
A rustic stone cottage is set against a backdrop of rolling hills. A spacious wooden deck extends from the cottage, surrounded by lush green grass and trees. Soft sunlight filters through the foliage, creating a serene outdoor environment.
Home in Derbyshire
4.84 out of 5 average rating, 468 reviews

Cosy cottage, stunning views near Chatsworth

If you want peace and solitude with stunning sunset views in a comfy, lived-in, dog-friendly place of your own Copy Wood Cottage is your ideal location. Situated on a steep hill above the Derwent Valley, it’s a short drive or good walk to Chatsworth and Bakewell and Matlock. Nestled on the edge of Beeley Moor Copy Wood sits below woodland and is surrounded by fields grazed by sheep. A short walk down brings to Rowsley village. We now have an EV Charger for guest’s use, just contact me on cost.

Top guest favourite
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
4.9 out of 5 average rating, 105 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 favourite
A charming stone exterior of the Coach House is highlighted, featuring a large arched entrance and a row of windows. The surrounding trees and blue sky create a serene environment, while the pathway leading to the entrance is flanked by stone walls and greenery.
Home in Bakewell
5 out of 5 average rating, 142 reviews

The Entire Coach House at Middleton Hall

Relax in this peaceful unique country home, either warm yourself by the wood burner or relax out in the garden, taking in the beautiful surroundings of the private Middleton Hall estate. The Coach House has been refurbished , with designer furniture, wall paper, hand painted murals on the walls, marble shower room, hypnos beds and an American fridge freezer. The attractions are wildlife, walking and cycling. Also visiting stately houses like Chatsworth and Haddon. coach-house-middleton.

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

Guest favourite
A view from a bridge showcases a serene countryside scene with a stone cottage nestled among lush greenery. The vibrant leaves of trees frame the picturesque surroundings, while the calm waters of the river reflect the natural beauty. The distant hills provide a backdrop.
Home in Froggatt
4.88 out of 5 average rating, 269 reviews

Bridgefoot Cottage - Wild Swimming & Hot Tub

Bridgefoot is a beautiful 17th century cottage situated in the Peak District. Guests have full use of the property including a modern, fully equipped kitchen, perfect for entertaining. There is also an exceptionally comfy and cosy sitting room, equipped with 2 sofas (one of which is a double sofa bed) a log burner and a Smart TV. The master bedroom boasts a luxurious four poster bed and an ensuite bathroom. Next door is a spacious second bedroom with two comfortable single beds.

Top guest favourite
The exterior of the cottage is adorned with a blend of natural stone and light-colored wood accents. Vibrant flowers in pink, white, and purple surround the entrance, enhancing the welcoming appearance. Two windows above the door allow natural light to brighten the charming facade.
Home in Youlgreave
4.99 out of 5 average rating, 243 reviews

Willow Cottage Newly renovated quaint cottage

Nestled away in the village of Youlgrave, in the heart of the Peak District National Park this newly renovated cottage is the perfect bolt hole for couples, friends and single travellers looking to get away from it all. It is a great place for walkers and cyclists with access to the Limestone Way, White Peak Way and the Alternative Pennine Way. There are three public houses which all serve home cooked food using local produce and there are two bakeries, a deli and post office.

Guest favourite
A charming stone barn exterior is framed by lush greenery. The building features several windows and is adorned with climbing vines and red leaves, creating a natural connection with its surroundings. A stone pathway leads to the entrance, enhancing the inviting appearance.
Home in Darley Dale
4.95 out of 5 average rating, 111 reviews

Hugo’s Luxury Barn

Welcome to Hugo’s Barn!! Nestled in the heart of the Peak District, Hugo’s Barn at Knabb Farm offers a luxurious and tranquil escape for couples, families, and dog lovers alike. Surrounded by stunning countryside, it’s the perfect retreat to unwind and explore the natural beauty of the region. Located just a short drive from Bakewell, Chatsworth, Matlock, and Matlock Bath, Hugo’s Barn provides a peaceful yet accessible base for your Peak District adventure.

Top guest favourite
Home in South Yorkshire
4.97 out of 5 average rating, 137 reviews

The Little Lodge

Kick back and relax in this calm, stylish space. The Little Lodge is a brand new renovated annex attached to a charming Victorian Lodge from the 1800s. Situated in a picturesque and peaceful conservation area on a private road in the leafy suburb of Ranmoor Sheffield. The Little Lodge is only 15minutes away from Sheffield's main train station and sits of the foothills of South Yorkshire's famous Peak District. Ideal for a city break or a Rambler's retreat.

Top guest favourite
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, 106 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.

Popular amenities for house rentals in Chesterfield

When is the best time to visit Chesterfield?

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Avg. price$121 SGD$123 SGD$121 SGD$134 SGD$129 SGD$127 SGD$151 SGD$161 SGD$146 SGD$152 SGD$142 SGD$151 SGD
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Quick stats about house rentals in Chesterfield

  • Total holiday rentals

    Explore 60 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 3,940 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Chesterfield holiday rentals include wifi 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!

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