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 ∙ 6 Guests - Chesterfield
10 2 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
This Peak District holiday home, located less than 1.6km from Matlock, offers easy access to attractions such as Gulliver's Kingdom (5.6km) and Bakewell (13.7km).
The 45 square metre, three-bedroom property sleeps six, boasting a multi-level layout with two lounges, a games room featuring table football and darts, and a secure storage area for bikes/motorbikes.
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.
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.
The Olde Coach House - Cottage With Hot Tub - Chesterfield
9.9 116 reviews

The Olde Coach House - Cottage With Hot Tub

cottage, Chesterfield
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.

Best Chesterfield cottages with a kitchen

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.
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.
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 ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 5 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Dronfield
This two-bedroom holiday home in Dronfield offers a rural base with easy access to Peak District attractions, including Chatsworth House (approximately 11 kilometers away) and Haddon Hall (approximately 16 kilometers away), as well as the market town of Chesterfield (approximately 8 kilometers away).
This family-friendly property accommodates up to four guests, featuring a fully equipped kitchen-diner, a lounge with an electric fire, two bathrooms, a garden with patio seating, and off-road parking, with a cot and highchair available on request.

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 3 best cottages with a jacuzzi

40 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

40 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Matlock Bath
This pet-friendly holiday cottage is located in a rural area near Matlock, offering a peaceful retreat 2 kilometers from Matlock Bath.
This self-catering property spans 40 square meters, accommodating up to four guests in two double bedrooms and featuring a well-equipped kitchen, three bathrooms, a coal fire, private garden, and internet access.
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.
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.

Best pet friendly Chesterfield cottages

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

Cedar Cottage - Chesterfield
No reviews

Cedar Cottage

cottage, Chesterfield
This Chesterfield cottage is situated 1.5km from the Barrow Hill Roundhouse Railway Museum, under 5km from Poolsbrook Country Park and the Technique Stadium, and less than 10km from Chesterfield Market and Mecca Bingo.
The self-catering holiday home offers free on-site parking, Wi-Fi in communal areas, two bathrooms, and allows pets; nearby attractions include outdoor activities at Poolsbrook Country Park and the football at the Technique Stadium.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
10 2 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage
Overton Cottage, a four-bedroom holiday home in Chesterfield, Derbyshire, is situated on the outskirts of the Peak District National Park, approximately 1.6 km from Chesterfield's Crooked Spire church and within easy reach of Hardwick Hall and Bolsover Castle.
This self-catering property sleeps eight guests and one dog, boasting a fully-equipped kitchen, private garden with summer house, and spacious sitting room with Smart TV; three double bedrooms, one twin with a sofa bed and TV, and a sleek bathroom complete the accommodation.
1 Bedroom Accommodation In Old Brampton, Near Chesterfield - Chesterfield
10 15 reviews

1 Bedroom Accommodation In Old Brampton, Near Chesterfield

cottage, Old Brampton, near Chesterfield
This cottage is located in a rural area near Chesterfield, offering convenient access to Chatsworth House and the Peak District National Park.
This pet-friendly holiday let accommodates two guests with one bedroom and one bathroom, featuring Wi-Fi, a garden, and proximity to walking routes and local amenities including a pub just 400 meters away.
2 Bedroom Accommodation In Old Brampton, Near Chesterfield - Chesterfield
10 13 reviews

2 Bedroom Accommodation In Old Brampton, Near Chesterfield

cottage, Old Brampton, near Chesterfield
This 2-bedroom holiday cottage in Old Brampton, near Chesterfield, is located in a rural setting approximately 3 minutes from moors and escarpments, offering direct access to countryside walks and nature trails, and is a short drive from Chatsworth House, Haddon Hall, and Hardwick Hall.
This family-friendly and pet-friendly property accommodates up to 4 guests with Wi-Fi, a garden, patio, and private parking for 2 cars, making it ideal for exploring local pubs (0.25 km away) and historic market towns.
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