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Chesterfield cottages
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26 Cottages at the best price in Chesterfield

Find Cottages in the City Centre of Chesterfield

Stay footsteps from vibrant local culture and top historical attractions at centrally located cottages in Chesterfield.

Cottage By The Park Chesterfield - Peak District - Chesterfield
9.7 113 reviews

Cottage By The Park Chesterfield - Peak District

cottage
This charming cottage is located just 15km from Baslow in the Peak District, offering a peaceful setting with a park on its doorstep, close to Chesterfield town center and Chatsworth Road. The cottage has received excellent user ratings for its location, cleanliness, and overall experience.
The property has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, a dedicated workspace, a private parking space, and an outdoor seating area perfect for relaxing in the summer months.
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 ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
10 2 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

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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.
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.

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
Oak Tree Retreat is a one-bedroom, one-bathroom cottage for two located in the Peak District countryside, offering immediate access to natural beauty. This open-plan living pod features a comfortable double bed, a Smart TV, a kitchen, complimentary Wi-Fi, and a sustainable Cinderella toilet, with private parking and a garden sitting-out area.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage
This country house is located on Jaggers Lane in Great Britain, within the Peak District National Park and set within 10 acres of woodland overlooking Darwin Lake, approximately 1.6 kilometers from local shops, pubs, and restaurants.
This family-friendly cottage offers accommodation for up to 8 guests with 4 bedrooms, 3 bathrooms, a well-equipped kitchen including a dishwasher, and private parking for 4 cars, with Wi-Fi and bed linen provided, and the Darwin Trail and Darwin Lake holiday village amenities accessible.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

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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 ∙ 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 most famous landmark. Then, explore the Chesterfield Museum and Art Gallery, which has a great collection of local history. In the evening, enjoy a meal at The Old Vicarage, a popular restaurant with a charming setting. On your second day, visit the beautiful Queen's Park, a green space with a boating lake. Afterwards, stroll through the historic streets of the town centre, and check out the independent shops and cafes.
  • 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 areas around the villages of Brampton, Hasland, and Clay Cross are perfect for renting a cottage. They offer a peaceful escape from the hustle and bustle of the town centre, with plenty of scenic walks and countryside views.
  • 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. The weather is mild, and the countryside is in full bloom. You can enjoy walks in the Peak District National Park and visit local markets without the crowds of summer.
  • 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. Then there's the Chesterfield Museum and Art Gallery, which has a fascinating collection of local history. For a bit of nature, Queen's Park is a lovely green space with a boating lake. And don't forget to visit the historic market square, with its charming independent shops and cafes.
  • 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 more secluded and peaceful experience compared to staying in a hotel. They often come with amenities like gardens and kitchens, allowing you to cook your own meals and enjoy the peace and quiet of the countryside.
  • What are the best pet friendly cottages in Chesterfield?

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

    Yes, Chesterfield town centre is easily walkable. For exploring the surrounding villages and countryside, cycling is a great option. There are several cycle paths and trails in the area, including the Chesterfield Canal towpath.
  • What are the best cottages with parking in Chesterfield?

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

    The Old Vicarage restaurant is a popular choice, with a beautiful garden setting. The restaurant at the Peak Edge Hotel also offers stunning views of the Peak District National Park.
  • What family-friendly activities are available in Chesterfield?

    Queen's Park is a great spot for families, with a playground, boating lake, and plenty of green space. The Chesterfield Museum and Art Gallery also has interactive exhibits that are fun for kids. For a day out, the National Trust's Hardwick Hall is a beautiful stately home with gardens that are perfect for a family picnic.

Popular destinations

Browse Cottages with a Hot Tub in Chesterfield

Indulge in a private hot tub-the ultimate detail to elevate your Chesterfield cottage city stay.

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 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.
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 ∙ 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.

Neighborhoods and points of interest in Chesterfield

Best Chesterfield cottages with a kitchen

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.
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.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

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Peak Avenue Retreat, a three-bedroom holiday home in Wingerworth, Derbyshire, is situated 4km from Chesterfield, offering easy access to the Crooked Spire church and the Peak District National Park.
This stylish, three-storey property sleeps five, boasts an enclosed garden, ultrafast Wi-Fi, two Smart TVs, and a bonus room; nearby attractions include Chatsworth House and Avenue Country Park.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage
Stubley Hollow 6 is a charming cottage located in Dronfield, just a short drive from both Sheffield and Chesterfield, with easy access to the Peak District National Park. The cottage is situated within 40 acres of land with over 30 horses, offering a peaceful and secluded escape.
This cosy dwelling is perfect for couples or a small family, with one bedroom and one bathroom. The cottage has a well-equipped kitchen, comfortable living space with a woodburner, and private parking for two cars.

Check Out Pet-Friendly Cottages in Chesterfield

Our pet-friendly cottages in Chesterfield guarantee a holiday your dog will enjoy as much as you.

The Bungalow@barlow, Pet Friendly, With Open Fire In Chesterfield - Chesterfield
10 1 review

The Bungalow@barlow, Pet Friendly, With Open Fire In Chesterfield

cottage, Dronfield
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.1 5 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
Thorntree Lodge, Pet Friendly, With A Garden In Ashover - Chesterfield
8.0 3 reviews

Thorntree Lodge, Pet Friendly, With A Garden In Ashover

cottage, Chesterfield
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.5 64 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Barrow Hill

Search Luxury Cottages in Chesterfield

Discover high-end character at a luxury cottage in Chesterfield city centre, offering sophisticated urban living.

Peak Avenue Retreat - Chesterfield
No reviews

Peak Avenue Retreat

cottage, Chesterfield

Popular Cottages with a Pool in Chesterfield

Take a dip whenever the mood strikes with on-site pool access at your Chesterfield cottage.

3 Bedroom Accommodation In Sheffield - Chesterfield
No reviews

3 Bedroom Accommodation In Sheffield

cottage, Sheffield

Discover Cottages with a Spa in Chesterfield

Begin your wellness journey at a cottage with a spa-the perfect sanctuary in the heart of Chesterfield.

Harry's Lodge, Pet Friendly, Character Holiday Cottage In Ashover - Chesterfield
No reviews

Harry's Lodge, Pet Friendly, Character Holiday Cottage In Ashover

cottage, Chesterfield
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