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 ∙ 8 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage
Hopton Cottage, a four-bedroom house near Two Dales, Derbyshire, sits 3 km from the village and on the edge of the Peak District National Park, offering easy access to attractions such as Haddon Hall and Chatsworth House.
This self-catering property sleeps eight, features a ground-floor super-king-size bedroom with en-suite wet room, a well-equipped kitchen with dishwasher, and a private patio; nearby amenities include a pub and grocery store.
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 ∙ 3 Bedrooms ∙ 5 Guests - Chesterfield
9.8 5 reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage
Churchside House is a charming end-terrace cottage located in Matlock, Derbyshire, just a short walk from the town centre and a 10-minute drive from the Peak District National Park. The cottage offers a peaceful retreat with views of St Giles' Church and is within walking distance of a local convenience store, pubs, and the River Derwent.
This 3-bedroom cottage can comfortably accommodate up to 5 guests and offers a fully equipped kitchen, a cosy living area, and a private garden with a patio for alfresco dining. Enjoy stunning views of the surrounding area, explore the local attractions, or simply relax and unwind in this peaceful cottage.

Best Chesterfield cottages with a kitchen

Riber, Family Friendly, Character Holiday Cottage In Two Dales - Chesterfield
No reviews

Riber, Family Friendly, Character Holiday Cottage In Two Dales

cottage, Matlock
This cottage is located near Two Dales in Derbyshire, just 1.6km from the Peak District National Park and a short drive from the charming town of Matlock. The cottage is perfect for families or groups of friends looking for a peaceful retreat in the heart of the Peak District.
The self-catering property has three bedrooms, sleeping up to seven guests, and includes a well-equipped kitchen with a dishwasher, a spacious living area with a wood-burning stove, and two bathrooms. The cottage also has a private patio with furniture and a fire pit, making it perfect for relaxing evenings outdoors.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.3 129 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

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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.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.6 7 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
This Derbyshire stone cottage, situated in Darwin Lake Holiday Village near the village of Two Dales, offers easy access to the Peak District National Park, Bakewell (approx. 10km), and Matlock (approx. 15km), placing you within easy reach of Haddon Hall and Chatsworth House.
The three-bedroom property sleeps six, features an open-plan living area with modern appliances, a ground-floor twin room with en-suite, two upstairs bedrooms with zip-and-link beds and en-suite facilities, plus a garden, parking, and internet access; pets are welcome.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Holymoorside
Mill Close Cottage, a delightful holiday home in Holymoorside, Derbyshire, enjoys easy access to the Monsal Trail and is within 20km of Chatsworth House and Bakewell.
This pet-friendly (dogs only) two-bedroom property offers ground-floor accessibility, sleeps four, includes a well-equipped kitchen and utility room, and boasts private parking for two cars.

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

Wigley Farm House Cottage, Pet Friendly, With Hot Tub In Chesterfield - Chesterfield
No reviews

Wigley Farm House Cottage, Pet Friendly, With Hot Tub In Chesterfield

cottage, Chesterfield
This Wadshelf cottage, located just a short drive from Chesterfield and serving as a gateway to the Peak District, offers convenient access to attractions such as Chatsworth House, which is a few kilometers away.
This 130 square meter holiday home accommodates up to six guests in three bedrooms and features a well-equipped kitchen, a sitting room with a woodburning stove, an enclosed garden with a hot tub, and parking for two cars.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 16 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

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Moor Farm Cottage, a Derbyshire self-catering property, is situated in the Peak District National Park, 3.2km from Ashover and 8km from Matlock, offering easy access to Chatsworth House and other historical sites.
This 105 square metre holiday home features two bedrooms sleeping four, a spacious open-plan living area, a private hot tub, on-site gym, and is close to walking and cycling trails.
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 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.

Best pet friendly Chesterfield cottages

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

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
Yew Tree Cottage, a self-catering holiday home in Matlock, Derbyshire, is centrally located for exploring attractions such as Chatsworth House (driving distance varies), Haddon Hall, and Crich Tramway Village.
This single-storey property offers two bedrooms sleeping four guests, a fully equipped kitchen with fridge, microwave, and dishwasher, off-road parking, and Wi-Fi; a decked balcony provides extra outdoor space.
Smithy Cottage - Chesterfield
10 1 review

Smithy Cottage

cottage, Dronfield
This pet-friendly Dronfield cottage offers self-catering accommodation less than 10km from the Peak District National Park, Mecca Bingo, and Queen's Park Cricket Ground.
The property includes a kitchen with a fridge and dishwasher, laundry facilities, and free on-site parking, plus free Wi-Fi in communal areas.
Overton - Chesterfield
No reviews

Overton

cottage, Chesterfield
This Chesterfield cottage is situated less than 2km from the Technique Stadium, Mecca Bingo, and Chesterfield Market, and within 5km of Queen's Park and Barrow Hill Roundhouse.
This pet-friendly self-catering property boasts two bathrooms, free Wi-Fi, and parking, offering convenient access to Chesterfield town centre and public transport.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.5 24 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
Thorntree Lodge, a three-bedroom log cabin, is situated 8km from Rowsley, Derbyshire, offering easy access to the Peak District National Park, Chatsworth House, and Haddon Hall.
This Peak District holiday home sleeps six, features an open-plan living area with a Smart TV, a well-equipped kitchen with dishwasher, a garden, and parking, and is close to Rowsley's amenities.
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