Cottage holiday rentals in Chesterfield

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Top-rated cottage rentals in Chesterfield

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Top Guest favourite
Cottage in Winster
4.95 out of 5 average rating, 432 reviews

Gorgeous romantic cosy cottage retreat with views

Welcome to Lancaster Cottage, Winster - the perfect luxury escape for couples in the Peak District. ~ Ideal cosy hideaway for a romantic escape for 2 ~ Secluded, off-road & immersed in nature with secret garden & log cabin ~Fabulous walks from the doorstep ~Lovely pubs within a few minutes walk ~Oozes character - built in 1701 & Grade II Listed ~ Cosy woodburner fireplace & beams ~Huge sink-in settee & a dreamy, romantic bedroom with king-sized comfy bed with stunning views ~Dog-friendly

Top Guest favourite
A cozy living room features an original stone fireplace with a real fire, flanked by comfortable seating. A green cabinet offers decorative items, while a warm lamp provides soft lighting. A traditional rug enhances the calm ambiance, creating a welcoming space for relaxation.
Cottage in Eyam
4.98 out of 5 average rating, 122 reviews

Romantic Little Cottage in Eyam, Peak District

Our quirky little dog friendly Peak District Cottage in Eyam has a style all of its own...Along with our shepherdshut we have been welcoming guests to our historic village for 10+ years. We believe in taking time out from busy lives & offering you a little bit of peace & quiet, somewhere to disconnect from your world & reconnect with each other. Memorial cottage sleeps 3, cosy, calm, comfy & oozes character, original beams, real fire, deep window seats to help you relax, unwind, escape, explore

Top Guest favourite
Cottage in Chesterfield
4.92 out of 5 average rating, 316 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 Birchover
4.99 out of 5 average rating, 235 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 comfortable seating on two plush sofas, arranged around a central ottoman. A stone fireplace with a woodburner creates a focal point. Exposed beams highlight the ceiling, while the space is adorned with floral cushions and a decorative area rug.
Cottage in Baslow
4.95 out of 5 average rating, 305 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 spacious lawn leads to a charming stone cottage, surrounded by well-maintained greenery. The bright blue sky and scattered clouds enhance the inviting atmosphere, while the driveway provides access to the property and its scenic surroundings.
Cottage in Bonsall
5 out of 5 average rating, 258 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 living area features a light-colored wall and hardwood flooring. A comfortable blue sofa with decorative cushions is positioned beside a modern coffee table. A flat-screen TV rests on a side unit, with a glimpse of a window providing natural light and a touch of greenery visible outside.
Cottage in Bakewell CP
4.95 out of 5 average rating, 406 reviews

Butts Cottage, Bakewell - Boutique, Cosy & Luxury

Butts Cottage is a Grade II 19th Century Georgian cottage centrally located in the famous bustling market town of Bakewell in The Peak District National Park. A perfect base for walking, visiting stately homes including Chatsworth and Haddon Hall, cycling or just simply relax and enjoy the endless unspoilt countryside of The Peak District. Newly renovated and completed in September 2019, the cottage offers everything you need for either a few days away to enjoy Derbyshire or a longer visit.

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, 329 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
The exterior of a quaint stone cottage is presented, featuring a textured stone facade. Flower baskets with vibrant blooms hang from the walls, and a small window is adorned with a grid pattern. A house number can be seen next to the door, adding character.
Cottage in Matlock Town
4.94 out of 5 average rating, 398 reviews

Cosy and quaint stone cottage full of character

A pretty stone built quaint cottage located a few minutes walk from the centre of Matlock with Victorian pubs, restaurants and antique shops on the edge of the Peak District national park. Full of character & charm, it boasts antique furniture, has a lovely living area, spacious double bedroom, en suite bathroom. Newly fitted modern kitchen with all amenities. Tastefully furnished throughout, it offers a mixture of old and new. A perfect romantic retreat, walkers paradise, outdoor activities.

Top Guest favourite
Cottage in Butterton
4.99 out of 5 average rating, 135 reviews

Idyllic cottage retreat

This romantic retreat is set in the heart of the picturesque village of Butterton which overlooks the beautiful Manifold Valley in the Peak District. The lanes are lined with pretty sandstone cottages and an idyllic ford runs through the cobbled street below the cottage and a great country pub is round the corner. This cosy hideaway is an ideal couples escape featuring a stunning bedroom with vaulted beamed ceiling and luxury features throughout. It has a boutique hotel feel in rural heaven.

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 Darley Dale
4.99 out of 5 average rating, 252 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.

Top Guest favourite
The charming cottage exterior is enveloped in lush greenery, featuring stone walls and a vibrant green door. A well-maintained pathway leads to the entrance, bordered by a variety of colorful plants and bushes, set against a backdrop of a clear blue sky.
Cottage in Monyash
5 out of 5 average rating, 305 reviews

Cosy Grade ll listed cottage Central Peak District

Nestled in the picturesque village of Monyash, Mereview a Grade II listed stone cottage offers the perfect escape for couples or solo adventurers seeking peace, character, and countryside charm. Thoughtfully restored and beautifully presented, this historic home blends timeless elegance with modern comfort. Whether you’re walking the limestone dales, visiting nearby Bakewell or Chatsworth House, or simply curling up with a book by the fire, this cottage is a serene base.

Popular amenities for Chesterfield cottage rentals

Quick stats about cottage rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $117 AUD per night before taxes and fees

  • Verified guest reviews

    Over 750 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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