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House vacation 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 favorite
Home in Rowsley
4.98 out of 5 average rating, 280 reviews

Panoramic views idyllic, hill farm 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

Top guest favorite
The lounge features a plush yellow sofa and a rustic wooden coffee table. Natural light enters through multiple windows, illuminating the charming space. A crystal chandelier hangs from the ceiling, while a cozy armchair and decorative plants add character to the inviting room.
Home in Wirksworth
4.98 out of 5 average rating, 124 reviews

Cosy hillside cottage with logburner and projector

Enjoy a unique and memorable stay at this quaint cottage in the historic town of Wirksworth, known as The Gem of the Peaks. Nestled on a pretty hillside street, Sunshine Cottage has beautiful views from the tiered patio garden and is less than 5 minutes walk from the town’s independent shops, boutique cinema and eateries. A cosy space for two filled with character and charm, the cottage has a lounge with logburner, kitchen diner, master bedroom with cinema-style projector and separate bathroom.

Guest favorite
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, 284 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

Guest favorite
The exterior of the stone cottage is featured, showcasing its classic design with multiple windows and a welcoming entrance. Hanging flower baskets add a touch of greenery, while the surrounding landscape displays lush grassland and rolling hills in the distance.
Home in Derbyshire
4.87 out of 5 average rating, 377 reviews

Runner Duck Cottage

A bright and airy cottage, comprising of two open plan rooms, a separate shower/WC. The kitchen area is equipped with hob, oven, fridge & microwave. In the downstairs lounge area there is a double pull out sofa bed, TV /DVD. Upstairs there is a king size bed & adjoining shower room/WC. Gas central heating. All bed linen, towels, and a welcome pack are provided. A charming little cottage for up to 4 people. Well behaved dogs are welcome. Immediate access to miles of footpaths & stunning views.

Guest favorite
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, 147 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 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 Derbyshire
4.9 out of 5 average rating, 103 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.

Guest favorite
A private terrace features a small table with two chairs, surrounded by stone walls. The stunning view showcases green hills and a partly cloudy sky. The rustic charm of the cottage's stone rooftop and chimneys adds to the peaceful ambiance.
Home in Darnall
4.88 out of 5 average rating, 177 reviews

Pigeon Loft Cottage

This unique self contained peaceful cottage is 250 years old and set in the centre of the beautiful village of Bonsall in the Peak District and within easy reach of all amenities. The cottage was once a Pigeon loft and has been transformed and renovated into a simple characterful living space within the conservation area. Views from the cottage and outside private terrace are stunning. There are choices of walks from the door including 2 pubs cafe and shop within easy 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, 341 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 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 Calver
4.88 out of 5 average rating, 268 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 favorite
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, 240 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 favorite
A warm living area is adorned with an orange sofa, layered with decorative pillows. A low table rests atop a patterned rug, while a guitar leans against a natural wood shelf featuring books and plants. Two windows invite natural light into the space.
Home in Grindleford
4.91 out of 5 average rating, 105 reviews

Peak District Home from Home!

We welcome you to our home. In the heart of the Peak District! Perfectly located for visiting Chatsworth, Haddon Hall, Bakewell & Sheffield. Comfortably sleeping four in two double rooms with a hidden single bed under the stairs ideal for someone who doesn’t mind a little less privacy. A spacious living and dining area with doors opening out onto a patio with a Hot Tub for four people & private garden. The house has comfy beds, boho decor & is really warm and cosy in winter.

Top guest favorite
A spacious bedroom features a large, comfortable bed dressed in pristine white linens. Two nightstands with lamps are positioned on either side, offering gentle illumination. A wardrobe is visible, and the soft beige walls create a calming environment.
Home in Baslow
4.94 out of 5 average rating, 430 reviews

Comfortable cottage on the Chatsworth Estate

Yeldwood Farm Cottage is a beautiful barn conversion on our farm, just outside Baslow. The self-catering cottage sleeps 2 guests, in a Super-King size (or Twin) master bedroom. The cottage comprises a fully equipped kitchen, dining room, sitting room and bathroom with a large bath and shower. We are ideally situated on the Chatsworth Estate within the Peak District, close to Chatsworth House itself, Haddon Hall, Bakewell, Eyam, Matlock, Castleton, Buxton and Sheffield.

Popular amenities for Chesterfield house rentals

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$19,875 GYDG$20,084 GYDG$19,875 GYDG$21,967 GYDG$21,130 GYDG$20,711 GYDG$24,686 GYDG$26,360 GYDG$23,850 GYDG$24,896 GYDG$23,222 GYDG$24,686 GYD
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Quick stats about house rentals in Chesterfield

  • Total vacation rentals

    Explore 60 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 3,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 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!

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