Cottage holiday rentals in Chesterfield

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Top-rated cottage rentals in Chesterfield

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

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Top guest favourite
Cottage in Darley Dale
4.96 out of 5 average rating, 307 reviews

The Hideaway. Great views, garden & location

The Hideaway is an attractive cottage with wonderful views, contemporary decoration, consisting of a kitchen/living space, bedroom, shower room & west facing balcony all accessed from your private entrance with self check-in. Hidden away on the lovely wooded hillside of the Derwent Valley between Bakewell and Matlock, within 3 miles of Chatsworth House & Haddon Hall. Great for walkers, situated down a quiet lane, with fantastic walks from the front door through woodland, fields or moorland. .

Top guest favourite
A cozy bedroom features a spacious bed dressed in white linens. Two rolled towels are positioned on the bed, adding a touch of hospitality. A wooden wardrobe stands nearby, and a framed artwork hangs on the wall, while natural light filters through the window, enhanced by dark curtains.
Cottage in Chesterfield
4.93 out of 5 average rating, 325 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.

Top guest favourite
Cottage in Youlgreave
5 out of 5 average rating, 203 reviews

Beautifully Restored; Spacious Spring Cottage

Spring Cottage is an ideal holiday destination for any family or friends. Completely renovated; spacious but cosy, so works for couples to 6 guests plus 1 infant (no pets). It has a lounge with log burner, large farmhouse kitchen with island & 10 ft (3m) dining table, en-suite, & peaceful south facing garden & seating area. In the centre of Youlgrave by the church; there’s many walks around the beautiful Georgian village/countryside with the Bradford & Laithkill Dales a short stroll away.

Top guest favourite
Cottage in Bakewell
4.99 out of 5 average rating, 238 reviews

Rocking Stone Cottage - Idyllic Rural Retreat

Perfect for two couples or a family an immaculate contemporary cottage in the Peak National Park, a stones throw from Chatsworth. A perfect spot to get away, relax and explore the stunning countryside right from the door. The cottage features beautiful outdoor spaces, a large stone fireplace with woodburning stove, wooden shutters, exposed beams, a fully fitted hand made kitchen, walk in rain showers and romantic roll top bath. BBQ on one of the two terraces or just relax and take in the view.

Top guest favourite
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, 324 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.

Top guest favourite
A gravelled courtyard is surrounded by charming stone buildings, their walls adorned with lush greenery. Potted plants and flowers add vibrancy to the outdoor space, while an ornamental stone feature sits at the center, creating a welcoming and serene atmosphere.
Cottage in Derbyshire
5 out of 5 average rating, 270 reviews

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

*AirBnB Best New Host Finalist 2022* A stunning 2 bedroom (Sleeps 4) luxury cottage, nestled in the Peak District countryside, with superb views over Chatsworth House. Outdoor dining, farm animals, private parking (with electric charging) & tranquil walks - all within a short drive of Bakewell, Matlock & the beautiful Derbyshire Dale villages. Fully equipped with everything you will need for your stay, including: Netflix, Amazon Prime & Disney+ BBQ for outdoor dining. Family & Dog Friendly

Top guest favourite
A cozy sitting area features a blue armchair with decorative pillow. A wooden mantel surrounds a small fireplace, flanked by two lamps providing soft illumination. Artwork adorns the walls, and a vintage trunk adds character to the space.
Cottage in Holymoorside
4.98 out of 5 average rating, 337 reviews

Wasp Nest Cottage, Peak District

Sitting on the edge of the Peak District, a stone’s throw from open fields, woodland and moors - sits a 19th Century cosy mill worker’s cottage. Two pubs and a shop are within easy walking distance and Chatsworth House is a beautiful 7 mile wander over the hill. Marvel at the lovely centuries old tree slice, coffee table and huge slice of elm breakfast bar, enjoy chopping boards, pottery and soft furnishings from the local artisans - just some of the magic the Peak District has to offer.

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 Matlock
4.99 out of 5 average rating, 269 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 favourite
A spacious lounge area features a modern sectional sofa, complete with decorative pillows. Soft light is provided by a standing lamp, highlighting the room's neutral tones. An archway leads towards a dining space that includes stylish pendant lighting, creating an inviting atmosphere.
Cottage in Derbyshire
4.91 out of 5 average rating, 263 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.

Guest favourite
The image depicts a serene outdoor view from a cottage, framed by lush greenery and climbing plants. A quaint wooden structure and a decorative swan sculpture are visible in the foreground. The landscape stretches into rolling hills under a clear sky, illuminated by soft sunlight.
Cottage in Derbyshire
4.9 out of 5 average rating, 135 reviews

Outstanding views at 2 Bed, dog friendly cottage.

Beautiful, eclectic artists cottage for relaxing in the Derbyshire Dales; the perfect place to explore and adventure, or just to relax and enjoy the views. Quirky 2 Bed, 2 Bath, 2 Lounge living with bifold doors to entrancing views of the Peak District. Garage parking, enclosed yard, dog friendly, inclusive and open to all. A 20min walk away from Matlock town centre with amazing walks, right from the door. Easy access to the Peak District with all its climbing, walking, running and biking.

Guest favourite
Cottage in Baslow
4.96 out of 5 average rating, 109 reviews

Contemporary Cottage Baslow

Charming & spacious cottage with modern decoration in the highly sought after village of Baslow. Within walking distance to Chatsworth House, just minutes walk from the edge of the estate. An ideal and spacious home to give a family of 4, a set of friends or 2 couples a holiday to remember. Featuring 2 double bedrooms, a spacious bathroom and additional downstairs toilet, spacious garden & patio, open plan kitchen and separate coZy lounge with log burner.

Top guest favourite
Cottage in Bradwell
4.97 out of 5 average rating, 434 reviews

5 Star Boutique 250 Year Old Peak District Cottage

Wake up to rolling hills and the picturesque little village of Bradwell. After walking through the scenery relax under our beautiful pergola with a well earned glass of wine or toast your toes in front of the log burner whilst the wind howls outside. We have restored Rambler Cottage to give you luxury and practicality, our bedding is divine, our towels envelope you in fluffiness. We care about your time spent with us and we want you to feel special

Popular amenities for cottage rentals in Chesterfield

Quick stats about cottage rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $128 SGD per night before taxes and fees

  • Verified guest reviews

    Over 810 verified reviews to help you choose

  • 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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