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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 ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
10 10 reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Barlow
This Derbyshire stone cottage, situated on the outskirts of Barlow near the eastern Peak District fringes, is 18.5km from Bakewell and 13km from Chatsworth House.
The self-catering property boasts a king-size bedroom with en-suite shower room, a fully equipped kitchen with fridge and dishwasher, smart TVs, off-road parking for two cars, and access to two acres of shared grounds including a babbling brook, sleeping up to two guests.
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.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.9 12 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Barlow
Smithy Cottage is a charming two-bedroom holiday home situated just 4.2 kilometres from Chesterfield, offering easy access to the Derbyshire countryside and the National Park. The cottage is located near the Peacock at Barlow, a popular pub with a great menu, and Barlow also has a children's play area.
This 105 square metre property can accommodate up to four guests and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as a relaxing front yard, a private driveway, and complimentary Wi-Fi.
Cottage By The Park Chesterfield - Peak District - Chesterfield
9.7 114 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.

Best family friendly Chesterfield cottages

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

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This two-bedroom holiday cottage is situated in the Bentley Brook Conservation Area of Matlock, Derbyshire, offering direct access to Peak District footpaths and being within 1.5 kilometers of Matlock's shops and pubs.
This pet-friendly, family-friendly property accommodates up to four guests and features a woodburning stove, a kitchen with a dishwasher, and a garden patio, with High Tor and Chatsworth House accessible within a short drive.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.8 20 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

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Harry's Lodge, a delightful cottage in Amber Valley, Derbyshire, is situated 5.3km from Ashover and 8km from Matlock, offering easy access to Chatsworth House, Bolsover Castle, and Bakewell.
This two-bedroom property sleeps four, boasting a contemporary open-plan living space with Smart TV, a fully equipped kitchen including a dishwasher, and private decking with country views; nearby attractions include the Peak Edge Hotel (1.6km) and numerous pubs in Ashover.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage
This ground-floor apartment, located at 58 Dale Road in Matlock, Derbyshire, offers a base near the Peak District National Park and within easy reach of local shops and riverside walks.
This one-bedroom cottage accommodates two guests and features a king-size bed, a fully equipped kitchen with a dishwasher, off-road parking for one vehicle, and an original fireplace in the sitting area.
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.

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 ∙ 1 Bedroom ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage
Highview Stables is a detached holiday home located on the outskirts of Chesterfield, Derbyshire, offering countryside views and proximity to Peak District attractions such as Chatsworth House and Bakewell.
This pet-friendly cottage accommodates up to four guests, featuring one double bedroom, a shower room, a woodburning stove, a fully equipped kitchen with a dishwasher, and off-road parking for two cars.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

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Wigley Farm House Cottage, a delightful bungalow near Wadshelf in Derbyshire, is situated 8km from Chesterfield, offering easy access to attractions such as Chesterfield's Crooked Spire.
This pet-friendly self-catering property sleeps six guests in three bedrooms (king, double, and twin), boasting a fully equipped kitchen, a hot tub, and an enclosed garden with patio furniture; nearby activities include exploring the tranquil Derbyshire countryside.
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

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Teversal
The Willows cottage, a three-bedroom house sleeping six, is situated on the Nottinghamshire/Derbyshire border near Teversal, a five-minute walk from the Teversal Trails and close to Sherwood Forest and Chesterfield.
This self-catering property boasts an open-plan living space with a wood-burning stove, a well-equipped kitchen including a dishwasher and wine cooler, two bathrooms (one en-suite), private parking for three cars, and a garden with barbecue.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
9.6 10 reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Hackney
This Peak District cottage, situated 1.6km from Matlock and 4.8km from the Heights of Abraham cable car, offers a romantic getaway in Hackney.
The 45 square metre property features one bedroom, one bathroom, sleeps two, and includes a kitchen with fridge, microwave, dishwasher, plus a garden, parking, internet access, and a wood burner; nearby attractions include pubs serving local ales and riverside walks in Matlock.
2 Bed In Chesterfield (Oc-49757) - Chesterfield
No reviews

2 Bed In Chesterfield (Oc-49757)

cottage, Upper Loads
This detached country house is located on the edge of the Peak District National Park, offering direct access to the countryside and situated a short distance from Chesterfield, with Chatsworth House and Gardens and Bakewell nearby.
This two-bedroom, two-bathroom cottage accommodates up to four guests and features a well-equipped kitchen with a dishwasher and Aga, a lounge with a wood burner, underfloor heating, an outdoor patio with a BBQ, and off-road parking for two vehicles.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
9.8 95 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Ashover
This four-bedroom stone cottage, a converted stable, is situated in the village of Ashover, Amber Valley, Derbyshire, approximately 8 kilometres from Matlock and close to Ashover's 9-hole golf course and the Crispin Inn.
The 145 square metre property boasts a country-style kitchen, separate dining room, large sitting room, private patio, lawned garden, and sleeps eight guests, with one en-suite bedroom; an adjoining property (Ref. 927577) offers potential for larger groups.

Check Out Pet-Friendly Cottages in Chesterfield

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

Highview Stables, Pet Friendly, With Hot Tub In Chesterfield - Chesterfield
No reviews

Highview Stables, Pet Friendly, With Hot Tub In Chesterfield

cottage, Chesterfield
Overton, Pet Friendly, Character Holiday Cottage In Chesterfield - Chesterfield
No reviews

Overton, Pet Friendly, Character Holiday Cottage In Chesterfield

cottage, Chesterfield
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.6 52 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
2 Bedroom Accommodation In Chesterfield - Chesterfield
No reviews

2 Bedroom Accommodation In Chesterfield

cottage, Chesterfield

Search Luxury Cottages in Chesterfield

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

The Loft At The George, Pet Friendly In Clay Cross - Chesterfield
No reviews

The Loft At The George, Pet Friendly In Clay Cross

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.

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Aston

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.

Overton - Chesterfield
No reviews

Overton

cottage, Chesterfield
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