Cottages in Chesterfield

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Chesterfield cottages
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26 Best cottages in Chesterfield

Top-Rated Family Cottages in Chesterfield

Give the family a holiday with real character and story at family cottages in Chesterfield.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Tansley
Oakwood Mews is a contemporary holiday home located in the rural village of Tansley, Derbyshire, just 3.2 kilometres from Matlock and on the edge of the Peak District National Park.
This single-storey cottage offers accommodation for four guests in two king-size bedrooms, featuring underfloor heating, a well-equipped kitchen/diner, a private enclosed courtyard, and is conveniently situated for exploring attractions such as Chatsworth House and Carsington Water.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This converted barn, offering a restful rural retreat, is located on the edge of the Peak District, 4.8 kilometres from Chatsworth House and a short drive from Bakewell.
This family-friendly cottage accommodates up to four guests across two bedrooms and one bathroom, featuring a well-equipped kitchen with a dishwasher, Wi-Fi, a garden with furniture, and private parking for two cars.
Barn Owls Nest-uk39432 - Chesterfield
10 2 reviews

Barn Owls Nest-uk39432

cottage, Dronfield
This Dronfield riverside cottage is situated within 4.8km of Dore & Totley Golf Club, Graves Park, Beauchief Abbey, Birch Hall Golf Club, and Abbeydale Industrial Hamlet, and an 18-minute walk from Dronfield railway station.
The self-catering property sleeps two guests in one bedroom and one bathroom, offering a fireplace, fully equipped kitchen, TV, internet access, free on-site parking, and proximity to waterside activities.
2 Bed In Holmesfield (Oc-pk783) - Chesterfield
No reviews

2 Bed In Holmesfield (Oc-pk783)

cottage, Dronfield
This Dronfield holiday home offers a rural retreat with easy access to Peak District attractions such as Chatsworth House, located a 9.5 kilometer drive away.
This family-friendly cottage accommodates four guests across two bedrooms and features a fully equipped kitchen, a lounge with an electric fire, two bathrooms, and a garden with patio seating, providing a comfortable base for exploring nearby Chesterfield and Sheffield.

Best Chesterfield cottages with a kitchen

2 Bed In Dronfield (Oc-pk612) - Chesterfield
10 1 review

2 Bed In Dronfield (Oc-pk612)

cottage, Barlow
Mulberry Cottage is a family-friendly holiday home located in the Peak District village of Barlow, offering convenient access to Chatsworth House and Hardwick Hall.
This 2-bedroom, 2-bathroom cottage accommodates up to 4 guests and features a well-equipped kitchen-diner, a private patio, a large garden with a Koi Carp pond, and off-road parking for 2 cars.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.7 6 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
This Derbyshire cottage is situated in the southern Peak District, 4.8km from Matlock and 7.2km from Matlock Bath, offering easy access to Chatsworth House (16km) and other Peak District attractions.
Sleeping six in three bedrooms (one super-king, one king-size en-suite, one double), this bungalow boasts a fully equipped kitchen, wood-burning stove, Wi-Fi, and a large south-facing garden; ideal for families exploring the Peak District National Park's walking and cycling trails.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
Plum Tree House is a charming bungalow located in Bradway, Sheffield, just a short distance from the scenic areas of Dore and Totley. The surrounding neighbourhood is quiet and peaceful, offering a relaxing escape from the city centre.
The bungalow can accommodate up to six guests in its three double bedrooms. It is equipped with a well-appointed kitchen, a private garden with a seating area, and off-street parking for two cars.
150 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
8.4 5 reviews

150 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

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This Tring-on-Tor hillside cottage overlooks Matlock, Derbyshire, offering stunning views and proximity (0.6km) to the town centre and its amenities, including shops, pubs, and restaurants, with easy access to the Peak District National Park.
The 150 square metre property boasts two bedrooms sleeping four, one bathroom, a well-equipped kitchen with a traditional stove, a south-facing patio, an open fire, and free on-street parking nearby.

Frequently asked questions about cottages in Chesterfield

  • When is the best time to rent a cottage in Chesterfield?

    Spring and autumn are lovely times to visit Chesterfield, as the weather is mild and the crowds are smaller. You'll enjoy the changing colours of the leaves in autumn and the blossoming flowers in spring. Summer is also a popular time to visit, but it can get busy.
  • What are the best cottages in Chesterfield?

    Among the cottages in Chesterfield, Wasp Nest Cottage - Peak District, Chatsworth Cottage and Peak District Perfection With Luxury Bath-sleeps 6 are the most popular ones.

  • What are the can't-miss sights in Chesterfield?

    The Crooked Spire is a must-see, of course! It's a unique and iconic landmark that you won't find anywhere else. Also, don't miss the Chesterfield Museum and Art Gallery, the beautiful Queen's Park, and the historic Chesterfield Market.
  • What are the best cottages with a pool in Chesterfield?

    The best cottage with a pool in Chesterfield is Cottage ∙ 2 Bedrooms ∙ 5 Guests.

  • Why consider renting a cottage in Chesterfield for your stay?

    Renting a cottage offers a more relaxed and comfortable experience than staying in a hotel. You'll have your own space, kitchen facilities, and often a garden or patio. It's a great way to feel more at home and enjoy a peaceful getaway.
  • What are the best cottages with a jacuzzi in Chesterfield?

    The best cottages with a jacuzzi in Chesterfield are The Olde Coach House - Cottage With Hot Tub, Tawny Owl Barn and Boundary Cottage.

  • Can you easily explore Chesterfield on foot or by bike?

    Yes, Chesterfield is a very walkable town. The town centre is compact and most attractions are within easy reach. You can also hire bikes from various locations in the town, which is a great way to explore the surrounding countryside.
  • What are the best cottages for families and kids in Chesterfield?

    The best cottages for families and kids in Chesterfield are Wasp Nest Cottage - Peak District, Chatsworth Cottage and Peak District Perfection With Luxury Bath-sleeps 6.

  • What are the best restaurants in Chesterfield with nature views?

    The Crooked Spire Bistro offers stunning views of the Crooked Spire and the town centre. The Old Vicarage is also a great option, with a beautiful garden and a peaceful atmosphere. You can enjoy a delicious meal while surrounded by nature.
  • What are the best pet friendly cottages in Chesterfield?

  • What family-friendly activities are available in Chesterfield?

    Queen's Park is a great place for a family day out, with a playground, boating lake, and plenty of open space for running around. The Chesterfield Museum and Art Gallery also has interactive exhibits that are fun for children. For a more active day, try the Chesterfield Bowl bowling alley or the Chesterfield Climbing Centre.
  • What are the best cottages with parking in Chesterfield?

Popular destinations

View All Cottages with a Hot Tub in Chesterfield

Retreat to a private sanctuary of hot bubbles right in your room at city cottages with a hot tub in Chesterfield.

The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe - Chesterfield
8.0 1 review

The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe

cottage, Dronfield
This converted Grade II listed stable, located in Millthorpe on the edge of the Peak District National Park, offers splendid valley views and is a short drive from Chatsworth House and Bakewell.
This 130 square meter cottage sleeps up to 7 guests across 3 bedrooms and features a separate building with a sauna and hot tub, alongside a garden with barbecue facilities and parking.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 47 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This semi-detached holiday home is located just a short distance from Matlock, a charming town in the heart of the Peak District National Park, offering breathtaking views of the Derbyshire Dales. The cottage is situated on the edge of the National Park, making it an ideal base for exploring the stunning scenery and outdoor activities on offer.
The cottage has two bedrooms and can comfortably accommodate up to four guests. It offers a range of amenities, including a fully equipped kitchen, a spacious garden, a hot tub, and a conservatory, making it perfect for relaxing and enjoying the beautiful surroundings.

Elite Pet-Friendly Cottages in Chesterfield

Welcome every member of the family, including your pet, at pet-friendly cottages in Chesterfield.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Barlow
This Barlow Country Park lodge is located in Barlow, South Yorkshire, on the edge of the Peak District National Park and close to the South Yorkshire border, offering 50 acres of pastures and woodland with 8 fishing lakes nearby.
This pet-friendly, family-friendly two-bedroom bungalow accommodates four guests, featuring an open-plan living space, a private garden, parking for two cars, and complimentary Wi-Fi, serving as a base for exploring the Peak District National Park.
Cottage ∙ 4 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 5 Guests

cottage
This accessible bungalow, Havendale, is located in historic Chesterfield, Derbyshire, just 1.4 kilometers from the medieval market town centre and its famous 'Crooked Spire', with the Peak District National Park, Chatsworth House, and Haddon Hall within easy driving distance.
This architecturally designed, single-storey property accommodates up to five guests in four bedrooms, featuring an open-plan living space with an accessible kitchen, a woodburning stove, and wide bifold doors leading to an enclosed south-facing garden with a barbecue, whilst pets and families are welcome.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
Carr House Farm, a farmhouse cottage on a working farm near Wingerworth, Derbyshire, offers woodland walks directly from the property and is conveniently located for day trips to Bakewell, Chatsworth, and Chesterfield. This family-friendly property accommodates up to six guests across three bedrooms, features a kitchen with a fridge, microwave oven, and dishwasher, and welcomes pets, with stables available on request.
4 Lovely Cottages Situated In The Beautiful Derbyshire Village Of Barlow. - Chesterfield
No reviews

4 Lovely Cottages Situated In The Beautiful Derbyshire Village Of Barlow.

cottage, Barlow near Bakewell
This one-bedroom holiday let is located in Barlow, Derbyshire, on the edge of the Peak District National Park and approximately 16 kilometres from Sheffield.
This pet-friendly cottage accommodates up to three guests, offering Wi-Fi, private parking for two cars, and a patio, set within 81 hectares of woodland and pastures with eight fishing lakes.

Book Top-Rated Luxury Cottages in Chesterfield

Escape the urban noise inside an intimate, design-forward timber sanctuary at luxury cottages in Chesterfield.

Cottage ∙ 1 Bedroom ∙ 3 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 3 Guests

cottage, Barlow

Top-Rated Cottages with a Pool in Chesterfield

Enjoy an exclusive swim in total privacy right in your own backyard at city cottages featuring a swimming pool in Chesterfield.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
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