Cottages in Chesterfield

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Chesterfield cottages
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26 Best cottages in Chesterfield

Top-Rated Family Cottages in Chesterfield

Give the family a holiday with real character and story at family cottages in Chesterfield.

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 ∙ 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.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

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Carr House Farm, a farmhouse cottage on a working farm near Wingerworth, Derbyshire, offers woodland walks directly from the property and is conveniently located for day trips to Bakewell, Chatsworth, and Chesterfield. This family-friendly property accommodates up to six guests across three bedrooms, features a kitchen with a fridge, microwave oven, and dishwasher, and welcomes pets, with stables available on request.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

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This studio-style lodge, Dore Cabin, is located on the outskirts of Sheffield, offering convenient access to the Peak District National Park, approximately 12 kilometers away, and the city's amenities.
This family-friendly accommodation for two features a kitchen with a fridge and microwave, a garden, and a rear patio, with proximity to shops, pubs, and local walks including Bamford Edge and Chatsworth House.

Best Chesterfield cottages with a kitchen

130 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 2 reviews

130 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

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This rural holiday home is located in Ashover, providing easy access to local amenities.
This 130 m² lodge accommodates up to 4 guests and features a fireplace, Wi-Fi, central heating, a fully equipped kitchen with a dishwasher, and a television.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Holymoorside
Yew Tree Cottage is a three-bedroom holiday home located in Holymoorside, Chesterfield, approximately 10km from Chatsworth House and within easy reach of the Peak District National Park.
This pet-friendly dwelling boasts two living areas, two bathrooms, a dishwasher, two wood-burning stoves, an enclosed garden with patio, private parking for two cars, and sleeps up to six guests, offering excellent access to walking trails and nearby pubs.
Cuckoo Nest, With A Garden In Ashover - Chesterfield
10 1 review

Cuckoo Nest, With A Garden In Ashover

cottage, Chesterfield
Cuckoo Nest is a charming one-bedroom cottage located in the peaceful village of Ashover, just five miles from Matlock and a short drive from local amenities. The village enjoys a tranquil setting, perfect for those seeking a relaxing escape.
The cottage is ideal for couples or a small family, offering a unique sleeping arrangement with a king-size bed and a sofa bed. Guests can enjoy modern amenities including a dishwasher, TV, and Wi-Fi, as well as a private garden with decking, furniture, and a barbecue.
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.

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, as the weather is mild and the crowds are smaller. You'll enjoy the changing colours of the leaves in autumn and the blossoming flowers in spring. Summer is also a popular time to visit, but it can get busy.
  • 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?

    The Crooked Spire is a must-see, of course! It's a unique and iconic landmark that you won't find anywhere else. Also, don't miss the Chesterfield Museum and Art Gallery, the beautiful Queen's Park, and the historic Chesterfield Market.
  • 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?

    Renting a cottage offers a more relaxed and comfortable experience than staying in a hotel. You'll have your own space, kitchen facilities, and often a garden or patio. It's a great way to feel more at home and enjoy a peaceful getaway.
  • 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 a very walkable town. The town centre is compact and most attractions are within easy reach. You can also hire bikes from various locations in the town, which is a great way 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 are the best restaurants in Chesterfield with nature views?

    The Crooked Spire Bistro offers stunning views of the Crooked Spire and the town centre. The Old Vicarage is also a great option, with a beautiful garden and a peaceful atmosphere. You can enjoy a delicious meal while surrounded by nature.
  • What are the best pet friendly cottages in Chesterfield?

  • What family-friendly activities are available in Chesterfield?

    Queen's Park is a great place for a family day out, with a playground, boating lake, and plenty of open space for running around. The Chesterfield Museum and Art Gallery also has interactive exhibits that are fun for children. For a more active day, try the Chesterfield Bowl bowling alley or the Chesterfield Climbing Centre.
  • What are the best cottages with parking in Chesterfield?

Popular destinations

View All Cottages with a Hot Tub in Chesterfield

Retreat to a private sanctuary of hot bubbles right in your room at city cottages with a hot tub in Chesterfield.

The Olde Coach House - Cottage With Hot Tub - Chesterfield
9.9 109 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.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 7 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Eckington
Courthouse Cottage is situated in Eckington, Derbyshire, just a short distance from the Peak District National Park and within walking distance of Eckington Park and the historic St Peter and St Paul's Church. This charming cottage offers a unique blend of historic charm and modern amenities.
This two-bedroom holiday home, spanning 105 square metres, comfortably accommodates up to four guests. You'll enjoy a private garden with a parasol for alfresco dining, a hot tub for relaxation, a fully equipped kitchen, and Smart TVs in both bedrooms.
2 Bedroom Accommodation In Old Whittington, Near Chesterfield - Chesterfield
10 6 reviews

2 Bedroom Accommodation In Old Whittington, Near Chesterfield

cottage, Old Whittington, near Chesterfield
Boundary Cottage, a semi-detached holiday home in Old Whittington, near Chesterfield, Derbyshire, is situated approximately 1.6km from Chesterfield town centre and 0.8km from a local pub, offering easy access to the Peak District National Park and attractions such as Chatsworth House and Haddon Hall.
This two-bedroom self-catering property sleeps five, boasting a jacuzzi, private garden with patio, parking for two cars, and modern amenities including a fully equipped kitchen, Freeview TV, Sky, Netflix, Playstation 4, and Nintendo Wii.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 47 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

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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.

Elite Pet-Friendly Cottages in Chesterfield

Welcome every member of the family, including your pet, at pet-friendly cottages in Chesterfield.

Cherry Tree Cottage, Pet Friendly, With Hot Tub In Chesterfield - Chesterfield
No reviews

Cherry Tree Cottage, Pet Friendly, With Hot Tub In Chesterfield

cottage, Chesterfield
Cherry Tree Cottage is situated near Chesterfield, Derbyshire, just 1.6 kilometres from the Peak District National Park, with a pub a short walk away.
The one-bedroom cottage, with a floor area of 90 square meters, comfortably accommodates four guests and features a fully equipped kitchen, a private covered hot tub, and a garden.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, Bolsover
This 1930s art deco holiday home in Bolsover, Derbyshire, is conveniently located for exploring the region, with Sherwood Forest 48 kilometres away and the Peak District under 1 hour's drive.
This pet-friendly cottage accommodates up to five guests across three bedrooms and two bathrooms, featuring a dishwasher, two open fires, Wi-Fi, and a garden with seating and dining areas, with a travel cot, highchair, and stairgate available on request.
Cottage ∙ 1 Bedroom ∙ 4 Guests - Chesterfield
9.7 11 reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage
Cherry Tree Cottage, a Peak District National Park holiday home near Chesterfield, Derbyshire, offers stunning views and easy access to Kinder Scout, The Roaches, and Dovedale walking trails, plus attractions like Chatsworth House and Haddon Hall, all within a short driving distance.
This 90 square metre (969 square feet) self-catering property boasts a king-size bedroom with en-suite, an open-plan living area with a double sofa bed, accommodating up to four guests, and features a private hot tub, swimming pool, and well-equipped kitchen including a dishwasher.
Cottage ∙ 4 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 5 Guests

cottage
This accessible bungalow, Havendale, is located in historic Chesterfield, Derbyshire, just 1.4 kilometers from the medieval market town centre and its famous 'Crooked Spire', with the Peak District National Park, Chatsworth House, and Haddon Hall within easy driving distance.
This architecturally designed, single-storey property accommodates up to five guests in four bedrooms, featuring an open-plan living space with an accessible kitchen, a woodburning stove, and wide bifold doors leading to an enclosed south-facing garden with a barbecue, whilst pets and families are welcome.

Book Top-Rated Luxury Cottages in Chesterfield

Escape the urban noise inside an intimate, design-forward timber sanctuary at luxury cottages in Chesterfield.

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage

Top-Rated Cottages with a Pool in Chesterfield

Enjoy an exclusive swim in total privacy right in your own backyard at city cottages featuring a swimming pool in Chesterfield.

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.5 24 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
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