Cottages in Chesterfield

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Chesterfield cottages
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26 Best cottages in Chesterfield

Best family friendly Chesterfield cottages

Among the 26 accommodations in Chesterfield, here are the 4 best family friendly cottages

Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chesterfield
9.8 16 reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, Old
Christmas Cottage, a three-storey stone house in Higham, Derbyshire, is situated near Ravensnest Wood and within easy driving distance (approximately 16km) of Matlock and the Peak District National Park.
This 130 square metre property sleeps five guests in three bedrooms (king-size, king-size, single with optional folding bed), features a fully equipped kitchen with dishwasher, a wood-burning stove, and a garden with barbecue; nearby attractions include Crich Tramway Village and the Heights of Abraham.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Bolsover
Greenwell Cottage, a four-bedroom house in Bolsover, is centrally located, a short walk from Bolsover Castle and within easy reach of the Peak District National Park.
This self-catering property sleeps eight, boasting a spacious kitchen with a large island, two living rooms (each with a Smart TV), a private hot tub, and ample parking; nearby activities include hiking in the Peak District.
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.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.5 64 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Barrow Hill
This Barrow Hill cottage, a former grocery store, is centrally located, a short walk from the Chesterfield Canal, Cuckoo Way, and the Trans-Pennine Trail, and a short drive (approx. 5km) from Chesterfield town centre and its attractions, including the Crooked Spire church and Queens Park.
The 130 square metre self-catering property sleeps six across three bedrooms, boasting a cosy sitting room with gas fire, a large garden ideal for children, and a fully equipped kitchen including a fridge, microwave, and dishwasher; nearby amenities include a children's playground and excellent access to walking and cycling trails.

Best Chesterfield cottages with a kitchen

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Kelstedge
Holly Cottage, a Peak District holiday home in Kelstedge, is conveniently located between Matlock (approx. 8km) and Chesterfield (approx. 16km), offering easy access to Matlock Bath and Chatsworth House.
This three-bedroom dwelling sleeps six, boasting a well-equipped kitchen with a dishwasher, two bathrooms, a private garden with a summerhouse, parking for three cars, and smart TVs in two bedrooms; a welcoming pub is directly opposite.
1 Bed In Dronfield (Oc-40971) - Chesterfield
No reviews

1 Bed In Dronfield (Oc-40971)

cottage, Chesterfield
This 1-bedroom holiday let is located in Barlow, within the Peak District National Park, offering access to Chatsworth House, Hardwick, and Haddon Hall within a 20-kilometre drive, and close to Bakewell.
This holiday cottage sleeps 2 guests and features a fully equipped kitchen, en-suite shower room, Smart TV, and a 2-acre garden with a BBQ and fire pit, plus off-road parking for 2 cars.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.1 5 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
The Botanical Flat 1, a three-bedroom duplex apartment in Sheffield's Sharrow district, is situated a short distance from Sheffield Botanical Gardens and a short drive (approximately 25-30km) from the Peak District National Park.
This pet-friendly self-catering property sleeps six guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, plus super-king, king and double bedrooms and a sleek shower room.
Cottage By The Park Chesterfield - Peak District - Chesterfield
9.7 117 reviews

Cottage By The Park Chesterfield - Peak District

cottage
This charming cottage is located just 15km from Baslow in the Peak District, offering a peaceful setting with a park on its doorstep, close to Chesterfield town center and Chatsworth Road. The cottage has received excellent user ratings for its location, cleanliness, and overall experience.
The property has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, a dedicated workspace, a private parking space, and an outdoor seating area perfect for relaxing in the summer months.

Frequently asked questions about cottages in Chesterfield

  • What would be a good 2-days itinerary for visiting Chesterfield?

    On your first day, head to the Crooked Spire, Chesterfield's famous landmark. Pop into the Chesterfield Museum and Art Gallery afterwards. For the evening, catch a show at the Pomegranate Theatre or enjoy a meal at one of the many restaurants in the town centre.
  • 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 part of Chesterfield is ideal for renting a cottage?

    The villages surrounding Chesterfield, like Hasland, Brampton, and Calow, are lovely for renting a cottage. They offer a peaceful escape while being within easy reach of the town centre.
  • What are the best cottages with a pool in Chesterfield?

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

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

    Spring and autumn are ideal for a cottage stay in Chesterfield. You'll enjoy pleasant weather and fewer crowds compared to the summer months.
  • 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.

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

    The Crooked Spire is a must-see, of course. You can't miss the Chesterfield Museum and Art Gallery, which tells the story of the town's history and culture. The Queen's Park is a lovely green space for a stroll.
  • 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.

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

    Cottages offer a charming and cosy alternative to hotels. They're perfect for families or groups of friends who want a home-away-from-home experience.
  • What are the best pet friendly cottages in Chesterfield?

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

    Chesterfield's town centre is easily explored on foot. You can also rent bikes from various places in the town, making it easier to explore the surrounding areas.
  • What are the best cottages with parking in Chesterfield?

  • What family-friendly activities are available in Chesterfield?

    The Chesterfield Museum and Art Gallery has interactive exhibits for children. The Queen's Park is perfect for a picnic or a game of frisbee. The nearby Peak District National Park offers plenty of opportunities for walks and outdoor activities.

Popular destinations

Best Chesterfield cottages with a jacuzzi

Among the 26 accommodations in Chesterfield, here are the 4 best cottages with a jacuzzi

Cottage ∙ 5 Bedrooms ∙ 10 Guests - Chesterfield
10 1 review

Cottage ∙ 5 Bedrooms ∙ 10 Guests

cottage, Oker
Ty Gambo is a five-bedroom cottage located in the village of Oker, Derbyshire, just 10km from the popular Peak District town of Matlock.
The 160 square metre property features a fully equipped kitchen, a spacious living room with a wood-burning stove, and a garden with a hot tub, perfect for relaxing after exploring the nearby Peak District National Park.
Cottage ∙ 7 Bedrooms ∙ 14 Guests - Chesterfield
9.0 9 reviews

Cottage ∙ 7 Bedrooms ∙ 14 Guests

cottage, Starkholmes
This Peak District holiday home, situated 5.6km above Matlock, offers easy access to Matlock town centre and its amenities, as well as the Peak Railway.
Sleeping up to 14 guests in seven bedrooms and five bathrooms across 45 square metres, the property boasts a state-of-the-art kitchen, games room with pool table, swimming pool, jacuzzi, and extensive garden with parking; pets are welcome.
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 ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
9.3 10 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage
This Matlock cottage, on Lime Tree Road, offers stunning views of Riber Castle and is conveniently located less than 0.2km from a pub and shop.
The 45 square metre property sleeps eight guests in four bedrooms, each with an en-suite (three) or access to a family bathroom; further amenities include a swimming pool, jacuzzi, garden, parking, and a games area with table football and darts.

Best pet friendly Chesterfield cottages

Among the 26 accommodations in Chesterfield, here are the 4 best pet friendly cottages

2 Bedroom Accommodation In Matlock - Chesterfield
10 1 review

2 Bedroom Accommodation In Matlock

cottage, Matlock
This Matlock riverside cottage, situated within 10km of attractions including Lumsdale Valley, Crown Square, Hall Leys Park, Matlock Bath Parks Country Park, and the Life in a Lens Museum, offers a tranquil escape.
Sleeping up to six guests in two bedrooms and two bathrooms, the self-catering property includes free parking, Wi-Fi, a fully equipped kitchen with a fridge and oven, and a TV; pets are welcome.
Cottage ∙ 1 Bedroom ∙ 3 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 3 Guests

cottage, Barlow
This Barlow holiday cottage is situated within 50 acres of conservation pastures and woodland, offering a tranquil natural environment close to the Peak District National Park and the South Yorkshire border.
This one-bedroom lodge accommodates up to three guests and features an open-plan living space with a gas fire, a zip and link super kingsize bed, complimentary Wi-Fi, and a patio with shared garden furniture, ideal for bird and wildlife spotting.
Mill Farm Cottages - The Nook - Chesterfield
No reviews

Mill Farm Cottages - The Nook

cottage, Barlow near Bakewell
This ground-floor holiday cottage in Barlow, Derbyshire, is situated on the edge of the Peak District National Park, just 5 kilometres from the South Yorkshire border, providing easy access to Bakewell Golf Club and Dore and Totley Golf Club.
This pet-friendly, family-friendly lodge accommodates two guests in one bedroom and offers private parking, free Wi-Fi, and an open-plan living area, set within 50 acres of grounds ideal for exploring the Peak District National Park and Longshaw Country Park.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, Inkersall
This Inkersall cottage, situated on the outskirts of Chesterfield, offers easy access to the Peak District National Park and is a short drive (distance unspecified) from Bolsover Castle.
The three-bedroom property sleeps five, features a well-equipped kitchen, utility room, private garden, and parking, providing comfortable accommodation for families or groups visiting Chesterfield and the surrounding area.
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