Cottages in Chesterfield at the best prices

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Chesterfield cottages
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26 Best cottages in Chesterfield

Best family friendly Chesterfield cottage rentals

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

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage
Stubley Hollow 6 is a charming cottage situated just 10km from the Peak District National Park, offering a peaceful escape from the city bustle. It's also conveniently located near Dronfield, a town with shops, restaurants and amenities.
This one-bedroom property can accommodate up to six guests and features a fully equipped kitchen with a dishwasher, a comfortable living space, and a bespoke bathroom. Guests can enjoy the rural setting, explore the Peak District, and even indulge in the equestrian activities on the 40-acre property.
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 ∙ 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.
2 Bed In Dronfield (Oc-pk612) - Chesterfield
No reviews

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.

Best Chesterfield cottages with a kitchen

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Tansley
Oakwood Lodge, a three-bedroom holiday home in Tansley, Derbyshire, is situated 3.2km from Matlock and offers easy access to the Peak District National Park, Bakewell, Chatsworth House, and Haddon Hall.
This pet-friendly self-catering property sleeps six, boasting a fully equipped kitchen/diner, a king-size bedroom with en-suite and TV, a private multi-level garden, and parking; a Smart TV in the sitting room provides additional entertainment.
Carr House Farm, Pet Friendly, With Open Fire In Wingerworth - Chesterfield
No reviews

Carr House Farm, Pet Friendly, With Open Fire In Wingerworth

cottage, Chesterfield
Carr House Farm, a detached barn conversion near Wingerworth, sits on the edge of the Peak District, offering access to open moorland and wooded dales, with a shop 900 meters and a pub 800 meters away.
This spacious 130 square meter property accommodates six guests in three bedrooms, features an open-plan living area with a woodburning stove, a separate sitting room with a Smart TV, and provides off-road parking, a courtyard, and the option of two stables for horses.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.3 129 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This first-floor apartment in Matlock, Derbyshire, offers stunning views of Riber Castle and Matlock church, and is a short drive (approximately 10km) from Bakewell and Ashover, the filming location for parts of the Peak Practice TV series.
Knowleston Place cottage sleeps four guests in two bedrooms, features a modern kitchen with a fridge and dishwasher, and provides free parking and Wi-Fi; enjoy its open-plan living area with mullioned windows overlooking Riber Castle.
Dore Cabin, Romantic, With A Garden In Sheffield - Chesterfield
No reviews

Dore Cabin, Romantic, With A Garden In Sheffield

cottage, Sheffield
Dore Cabin is a studio cottage located on the outskirts of Sheffield, South Yorkshire, 160 meters from local shops and pubs, and close to the Peak District National Park.
This 90 square meter holiday home accommodates two guests with one bedroom and one bathroom, featuring a kitchen with a fridge and microwave oven, central heating, WiFi, a private patio, and access to a communal garden, with easy access to Sheffield's Crucible Theatre and Millenium Gallery via the super tram.

Frequently Asked Questions about cottages in Chesterfield

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

    On your first day, visit the Crooked Spire, have a look around Chesterfield Market, and maybe have a pint at a traditional pub like The Old House. On your second day, head to the Chesterfield Museum and Art Gallery, and then enjoy a walk along the canal in the afternoon.
  • What are the best cottage rentals in Chesterfield?

    Among the cottage rentals 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 areas around Hasland, Staveley, and Brampton are popular for cottages, offering a quieter setting while still being close enough to the town centre.
  • What are the best cottage rentals with a pool in Chesterfield?

    The best cottage rental 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 lovely in Chesterfield, with mild weather and fewer crowds. You can enjoy the colours of the changing leaves and the blossoming spring flowers.
  • What are the best cottage rentals with a jacuzzi in Chesterfield?

    The best cottage rentals with a jacuzzi in Chesterfield are The Olde Coach House, Tawny Owl Barn and Boundary Cottage.

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

    The Crooked Spire is a must-see, of course! The Chesterfield Museum and Art Gallery is worth visiting, and you can also explore the beautiful Queen's Park.
  • What are the best cottage rentals for families and kids in Chesterfield?

    The best cottage rentals 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 more homely and comfortable experience than a hotel, and you can often find ones with lovely gardens and countryside views. They are also perfect for families or groups of friends.
  • What are the best pet friendly cottage rentals in Chesterfield?

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

    Yes, the town centre is compact and easily walkable. There are also bike paths along the canal and in Queen's Park, making it a great option for exploring the wider area.
  • What are the best cottage rentals with parking in Chesterfield?

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

    The restaurant at the Peak District Hotel has fantastic views of the surrounding countryside, and The Old Vicarage in Brampton offers a picturesque setting with a garden terrace.
  • What family-friendly activities are available in Chesterfield?

    Queen's Park has a playground, a boating lake, and a mini golf course. The Chesterfield Museum and Art Gallery has interactive exhibits for children, and the Chesterfield Canal is perfect for a leisurely stroll.

Popular destinations

Best Chesterfield cottage rentals with jacuzzi

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

Cottage ∙ 3 Bedrooms ∙ 4 Guests - Chesterfield
9.3 9 reviews

Cottage ∙ 3 Bedrooms ∙ 4 Guests

cottage
This Derbyshire Dales holiday home is situated 3.2km from Matlock, offering easy access to Peak District attractions such as Chatsworth House and the Heights of Abraham within a 21km radius.
The three-bedroom property sleeps four adults and one child, boasting a wood-fired hot tub, Smart TVs, and a well-equipped kitchen with a dishwasher and Nespresso machine.
Cottage-sdb Privée Avec Douche-the Olde Coach Hous - Chesterfield
9.9 109 reviews

Cottage-sdb Privée Avec Douche-the Olde Coach Hous

cottage
This charming cottage is located in Chesterfield, just a 1.2 kilometre walk from Mecca Bingo, Chesterfield Market, and Queen's Park, offering easy access to local attractions. The property has received excellent ratings for its cleanliness, location, and overall experience.
The 3-bedroom cottage spans 120 square metres and provides a comfortable and spacious home away from home. Guests can enjoy a range of amenities including a Jacuzzi, a private garden, a fitness centre, two tennis courts, and free parking.
Cottage ∙ 1 Bedroom ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage
Highview Stables is a detached holiday home located on the outskirts of Chesterfield, Derbyshire, offering countryside views and proximity to Peak District attractions such as Chatsworth House and Bakewell.
This pet-friendly cottage accommodates up to four guests, featuring one double bedroom, a shower room, a woodburning stove, a fully equipped kitchen with a dishwasher, and off-road parking for two cars.
Highview Stables, Pet Friendly, With Hot Tub In Chesterfield - Chesterfield
No reviews

Highview Stables, Pet Friendly, With Hot Tub In Chesterfield

cottage, Chesterfield
Highview Stables, a self-catering property in Chesterfield, Derbyshire, is situated 0.5km from a pub and bus stop, and 5.3km from the nearest shop, offering easy access to the Peak District National Park and Chesterfield's historic town centre, including the Crooked Spire church.
This one-bedroom cottage boasts 90 square metres of floor space, accommodating up to four guests, and features a well-equipped kitchen, a jacuzzi, a garden, off-road parking for two cars, and a wood-burning stove in the sitting room.

Best pet friendly Chesterfield cottage rentals

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

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Ashover
This first-floor apartment, Little Mill, is located in Ashover, Derbyshire, set within an old mill beside the River Amber, 8 kilometers from Matlock and close to Chatsworth House and Haddon Hall.
This pet-friendly, family-friendly cottage sleeps two guests in one bedroom, offering a well-equipped open-plan living space with a kitchen, a sitting area with an electric fire, an en-suite shower room, and a garden with river views, plus shared grounds with picnic facilities and bike storage.
Cottage ∙ 4 Bedrooms ∙ 7 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 7 Guests

cottage
This pet-friendly, four-bedroom holiday cottage is located on Jaggers Lane within the Peak District National Park, a short drive from the M1 motorway and offering access to market towns and outdoor pursuits.
This architect-designed stone property, accommodating up to seven guests, features an open-plan living space and is situated within a holiday village with 10 acres of grounds and a 3-acre lake, providing opportunities for hiking, cycling, and fishing, with attractions like Chatsworth House and Carsington Water nearby.
3 Bedroom Accommodation In Ashover, Near Matlock. - Chesterfield
No reviews

3 Bedroom Accommodation In Ashover, Near Matlock.

cottage, Ashover, near Matlock.
This three-bedroom riverside property in Ashover, near Matlock, is situated within 9.6km of Lumsdale Valley, Crown Square, and Hall Leys Park, offering easy access to Matlock's attractions and the Derbyshire Dales.
The self-catering dwelling sleeps six, boasts two bathrooms, a fully equipped kitchen with dishwasher, garden, parking, internet access, and a washing machine, perfect for exploring the picturesque Peak District.
Cottage ∙ 2 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 5 Guests

cottage
This end-terrace holiday home, Baytree House, is situated on Rushley Road in Sheffield, South Yorkshire, offering a practical base for exploring Sheffield's city attractions and the Peak District, with local pubs and shops within a 500-meter walk. This two-bedroom cottage accommodates up to five guests, featuring an open-plan living area with a kitchen, a ground-floor wet room and cloakroom, enclosed rear patio, and off-road parking for three cars, ideal for families and groups seeking self-catering accommodation near Sheffield's parks and museums.
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