Cottage vacation rentals in Chesterfield

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Top-rated cottage rentals in Chesterfield

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Top guest favorite
The living room features a cozy arrangement with a soft beige sofa and armchair, adorned with floral cushions. A low coffee table sits in front of a fireplace, while patterned curtains frame a bright window. A small TV is mounted on the wall above the fireplace.
Cottage in Chesterfield
4.93 out of 5 average rating, 308 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 favorite
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 Darnall
5 out of 5 average rating, 233 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 favorite
The traditional stone cottage features a sloped roof and an inviting exterior surrounded by lush greenery. The garden is well-maintained, showcasing various shrubs and trees. A gravel pathway leads visitors to the entrance, while additional buildings are visible to the side.
Cottage in Derbyshire
4.97 out of 5 average rating, 144 reviews

Pretty detached stone cottage in Derbyshire Dales.

Traditional detached stone cottage in peaceful countryside on the outskirts of Dethick, Lea and Holloway. Situated near the confluence of Littlemoor and Lea Brooks amidst trees and fields, Brook Cottage provides a relaxing bolthole: perfect for a romantic getaway for two or as a base for exploring the Dales and Peaks for up to four. Great walks and cycling from the doorstep. Tourist spots such as Matlock, Bakewell, Cromford and Chatsworth House easy to reach by car. Short walk to village pub.

Top guest favorite
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, 309 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 favorite
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 Derbyshire
4.94 out of 5 average rating, 368 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 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, 219 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 favorite
Cottage in Winster
4.95 out of 5 average rating, 407 reviews

Gorgeous romantic cosy cottage retreat with views

Welcome to Lancaster Cottage, Winster - possibly the best situated cottage in the Peak District - utterly peaceful yet an easy stroll to pubs and fantastic walking trails from the doorstep. Built in 1701 & Grade II Listed, it oozes character and is the ideal cosy winter retreat for a romantic escape for 2. Cosy fireplace & beams, huge settee & a dreamy, romantic bedroom with king-sized comfy bed with lovely views over the hills, plus 2 outdoor seating areas & a log cabin in the garden.

Top guest favorite
A charming outdoor area features a gray hydrotherapy hot tub surrounded by lush greenery. Nearby, pastel pink chairs invite relaxation, with towels neatly arranged and a small table presenting refreshments. The rustic stone wall adds character to the private garden setting.
Cottage in Derbyshire
5 out of 5 average rating, 228 reviews

Jack's Cottage, Curbar

Sleeping on a cloud under Curbar Edge. Take it easy at Jack's Cottage, a boutique 17th century stone built luxurious cottage in the heart of the Peak District. Enjoy a soak in the hydrotherapy hot tub or cosy up in front of the log burner. Located next to the historic well in the centre of the village with a fully fenced private garden, bring your dog along to explore amazing walking and cycling from the doorstep. Secure alarmed bike store with wall anchor & charge for ebikes.

Guest favorite
The exterior of Pepper Cottage is visible, showcasing a traditional stone façade with multiple windows. Access steps lead up to the entrance, and a low fence borders the well-kept garden area. The surrounding neighborhood features a mix of architecture under a bright blue sky.
Cottage in Derbyshire
4.95 out of 5 average rating, 197 reviews

Pepper Cottage- pet-friendly, stylish & cosy

Pepper Cottage is a stylish yet traditional workman's cottage with a modern garden room extension situated on Church Street, about 5-10mins walk into the centre of Matlock. It is ideal for dog-owners as it has a fenced garden and easy access to the High & Pic Tor for walks with fantastic views across Matlock & down to Matlock Bath. The front of the cottage looks up to Riber Castle. There is a lockable garden shed for bikes. Ideal for couples & families with older children.

Top guest favorite
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, 281 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.

Superhost
An indoor heated swimming pool is featured with a rounded design, surrounded by large glass windows that provide natural light and views of the outdoors. Two steps lead into the pool, which is bordered by a tiled area. Loungers are placed nearby for relaxation.
Cottage in Rowsley
4.86 out of 5 average rating, 189 reviews

Cosy Woodside Cottage, indoor pool, nr Chatsworth

Charming cosy cottage within 9 acres of gardens and all year round indoor heated swimming pool, shared only with The Round House , also available to book. Walk directly to Chatsworth House (3 miles) along the River Derwent - come back and curl up by the fire. Listen to birdsong and savour the stunning views from the garden. You will find brand new comfy beds, new (downstairs) family bathroom and brand new well equipped cream Shaker kitchen with separate pantry.

Top guest favorite
The exterior of the cottage features a blend of rustic brick and wooden elements, with a welcoming entrance and landscaped planters. The path is bordered by well-kept greenery, leading toward the charming structure under a partly cloudy sky.
Cottage in Totley
4.99 out of 5 average rating, 229 reviews

Luxury Peak District Cottage with Hot Tub

The Old Stable Block at Bank View Farm has recently been converted into an elegant self-catering holiday cottage with its own private hot tub in a beautiful courtyard garden. The cottage is set in the wonderful landscaped grounds and gardens of bank view farm next to the orchard with its geese and giant tortoises. Set on the edge of the peak district moors with pubs on your doorstep, this is the perfect location for an idyllic rural retreat.

Popular amenities for Chesterfield cottage rentals

Quick stats about cottage rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

  • Verified guest reviews

    Over 720 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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