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Chesterfield cottages
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26 Cottages at the best price in Chesterfield

Best family friendly Chesterfield cottages

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

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Barlow
This holiday let is situated in Barlow, Derbyshire, on the edge of the Peak District National Park and near the South Yorkshire border, offering easy access to 50 acres of conservation pastures, lakeland, and woodland.
This ground-floor lodge accommodates two guests and one pet, featuring a kitchen, a shared patio, and free Wi-Fi, making it ideal for exploring the surrounding natural beauty.
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 Bedroom Accommodation In Dronfield - Chesterfield
10 1 review

1 Bedroom Accommodation In Dronfield

cottage, Dronfield
This one-bedroom apartment is situated in Dronfield, a town on the edge of the Peak District National Park, just 10km from Sheffield and 15km from Chesterfield, offering a peaceful escape from the city. The apartment is part of a converted barn on a 40-acre gated property with over 30 horses, perfect for a relaxing getaway.
The apartment has an open-plan living space ideal for two guests, with a well-equipped kitchen and comfortable sofas. Enjoy free WiFi, a dishwasher, a coffee machine, private parking for two cars, and easy access to local shops, restaurants, and attractions like the Peak District, Chesterfield, and the charming village of Hathersage.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This barn conversion is situated in Ashover, on the edge of the Peak District National Park, offering spectacular views towards Riber Castle and proximity to Chatsworth and Matlock, with Ashover village and its pubs 800 meters away.
This cottage sleeps four guests across two bedrooms and features a Rangemaster cooker in the spacious kitchen, a gas imitation woodburner in the sitting room, a four poster bed, and is conveniently located for exploring the Peak District.

Best Chesterfield cottages with a kitchen

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.
1 Bed In Dronfield (Oc-52026) - Chesterfield
No reviews

1 Bed In Dronfield (Oc-52026)

cottage, Barlow
This Barlow cottage is located in the Peak District, 1 hour by car from major industrial cities and near Chatsworth House and the Peak District National Park.
This 1-bedroom lodge for 2 guests offers a well-equipped kitchen with a Nespresso machine, a lounge with a wood burner, and off-road parking for two cars, with access to miles of footpaths and cycle ways.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.9 36 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Handley
This Handley holiday home, a converted 19th-century Methodist chapel, overlooks Ogston Reservoir in Derbyshire and is a short drive from Bakewell, Matlock, and Ashbourne.
The two-bedroom dwelling, sleeping four, boasts an open-plan living area with an electric wood-burning stove, a country-style kitchen with dishwasher, and a family bathroom; enjoy reservoir views from Velux windows and explore nearby Peak District attractions.
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.

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. The weather is mild, the colours are stunning, and you'll avoid the crowds of summer. Plus, you'll be able to enjoy the local markets and events.
  • 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?

    You absolutely must see the Crooked Spire, the iconic landmark of Chesterfield. Don't miss the Chesterfield Museum, which tells the story of the town's history. And if you're a fan of nature, a trip to Queen's Park is a must.
  • 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?

    A cottage offers a unique and comfortable experience. You'll be able to relax and unwind in a peaceful setting, away from the hustle and bustle of the town. Plus, you'll be close to the beautiful countryside, perfect for exploring.
  • 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 very walkable. The town centre is compact, and you can easily explore the main attractions on foot. There are also plenty of cycle paths, making it easy 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 family-friendly activities are available in Chesterfield?

    Queen's Park is a great place for kids, with a playground, paddling pool, and plenty of space to run around. The Chesterfield Museum also has a family-friendly section with interactive exhibits.
  • What are the best pet friendly cottages in Chesterfield?

  • What are the best cottages with parking in Chesterfield?

Popular destinations

Best Chesterfield cottages with a jacuzzi

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

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.
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 ∙ 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.
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

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Woolley Moor
Perkins Cottage, a three-bedroom house in Woolley Moor, Derbyshire, offers easy access to Ogston Reservoir and the Peak District National Park, with Matlock approximately 8km away.
This self-catering property sleeps six, features a well-equipped kitchen with a dishwasher, an enclosed garden with BBQ, private parking for three cars, and free Wi-Fi, all within 0.2km of a pub and restaurant.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
10 9 reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Tansley
This stone cottage near Tansley, Derbyshire, is situated 3.2km from the Peak District National Park and 2.4km from Matlock, offering easy access to Lumsdale Falls, Ogston Reservoir, and the Heights of Abraham.
The one-bedroom property, sleeping two with a pet-friendly policy, features a super-king-size zip-and-link bed (twin option available), an open-plan living area with a wood burner-style gas fire, a stylish bathroom with a freestanding bath and shower, off-road parking for two cars, and a private enclosed courtyard garden with BBQ facilities.
Cottage ∙ 2 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 6 Guests

cottage, Kelstedge
This Peak District cottage in Kelstedge is conveniently located above a local pub, offering easy access to the Peak District National Park's walking trails and attractions, though precise distances to specific landmarks aren't provided.
Sleeping up to six guests, the self-catering property comprises two bedrooms (one double with en-suite, one twin), two bathrooms, a well-equipped kitchen, a living room with a sofa bed and Freeview TV, plus free Wi-Fi and parking for two cars; dogs are welcome.
Cottage ∙ 2 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 5 Guests

cottage
Ryecroft Cottage sits on a hill overlooking Matlock town centre, just a short drive from the picturesque market town of Bakewell. The cottage is conveniently located within walking distance of shops, cafes, restaurants, and pubs, and is also close to major attractions like Chatsworth and Haddon Hall.
The cottage has two bedrooms, one with a double and single bed, and a bathroom with a separate shower and bath, making it ideal for families of up to five people. The cottage also offers a spacious kitchen with a dishwasher, two living rooms with woodburning stoves, a private garden, bike storage, and on-road parking.
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