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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.
Yew Tree Cottage - Chesterfield
9.4 7 reviews

Yew Tree Cottage

cottage, Holymoorside
Yew Tree Cottage is located in the peaceful village of Holymoorside, just 6km from Chatsworth House and within easy reach of the Peak District National Park. The cottage has received excellent ratings for cleanliness, location, and user experience.
This 3-bedroom, 2-bathroom property comfortably accommodates up to 5 guests. The cottage provides a spacious kitchen/dining room, two living rooms with wood-burning stoves, a private enclosed garden with a patio, and private parking for two cars. Guests can enjoy the nearby pubs, shops, and restaurants, as well as numerous walking trails leading to Linacre Reservoir and Matlock.
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.
2 Bedroom Accommodation In Holymoorside - Chesterfield
10 4 reviews

2 Bedroom Accommodation In Holymoorside

cottage, Holymoorside
This charming cottage is located just 5 kilometres from the Peak District National Park, offering easy access to the stunning scenery and walking trails of the area. It's also within easy reach of Chesterfield, with its historic market and museums, as well as Queen's Park and Mecca Bingo for entertainment.
The cottage has two bedrooms and can accommodate up to four guests. It comes equipped with modern amenities, including a washing machine, TV, and a kitchen with a dishwasher, as well as a private garden for relaxing and enjoying the fresh air.

Best family friendly Chesterfield cottages

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

Courthouse Cottage, Eckington. - Chesterfield
No reviews

Courthouse Cottage, Eckington.

cottage, Sheffield
Courthouse Cottage, situated in Eckington, Derbyshire, is a 2-bedroom holiday let offering convenient access to Sheffield's cultural sites, including Kelham Islands Museum and the National Videogame Museum, located 8-16 kilometers away, and is also a short drive from the Peak District National Park.
This pet-friendly accommodation sleeps four guests and features an enclosed garden with a hot tub, a well-equipped kitchen/diner, a sitting room with a Smart TV, and roadside parking for two cars.
3 Bedroom Accommodation In Inkersall, Near Chesterfield - Chesterfield
No reviews

3 Bedroom Accommodation In Inkersall, Near Chesterfield

cottage, Inkersall, near Chesterfield
This Inkersall riverside cottage, near Chesterfield, is 1.8km from Poolsbrook Country Park, 5km from the Barrow Hill Roundhouse Railway Centre, and under 5km from the Pomegranate Theatre.
Sleeping five guests, this three-bedroom holiday home boasts a fully equipped kitchen, private patio, garden, parking, and Wi-Fi; enjoy nearby waterside activities or explore Chesterfield's attractions.
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.
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.

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.

3 Bed In Matlock (Oc-86482) - Chesterfield
No reviews

3 Bed In Matlock (Oc-86482)

cottage, Hackney
This converted barn, offering 3 bedrooms and sleeping 4 guests, is situated in the Derbyshire Dales, 2 kilometres from Matlock and 6 kilometres from the Chatsworth Estate, providing uninterrupted views of the hillsides from its working farm setting. Guests can enjoy a wood-fired hot tub, a lounge with a wood burner, and direct access to a woodland walk with a waterfall, with the cottage also featuring a dishwasher, washing machine, and tumble dryer.
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.
3 Sunnyside Terrace, Pet Friendly, With Hot Tub In Matlock - Chesterfield
No reviews

3 Sunnyside Terrace, Pet Friendly, With Hot Tub In Matlock

cottage, Matlock
This semi-detached cottage is located in Farley, just a mile from shops and a short walk from a pub, making it a convenient base for exploring the Peak District. The cottage is perfect for a family or group of friends, sleeping up to four guests comfortably in two double bedrooms.
The cottage has a private hot tub, a woodburning stove, and an enclosed garden, perfect for relaxing after a day exploring the area. You can also enjoy modern amenities like a dishwasher, washing machine, and Smart TV with Netflix.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
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.

Neighborhoods and points of interest in Chesterfield

Best Chesterfield cottages with a kitchen

The Gatehouse, Pet Friendly, Character Holiday Cottage In Mansfield - Chesterfield
No reviews

The Gatehouse, Pet Friendly, Character Holiday Cottage In Mansfield

cottage, Sutton-in-Ashfield
The Gatehouse is a stone-built holiday home located in Teversal, just 2.5 kilometres from Mansfield and a short drive from Sherwood Forest and Robin Hood's Wheelgate Park, making it a great base for exploring Nottinghamshire. The property is a spacious four-bedroom house that can comfortably sleep up to eight guests, ideal for families or groups of friends. The Gatehouse offers a range of amenities, including a large garden with a hot tub, a games room with table football and air hockey, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.8 46 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Two Dales
Toad Cottage, a delightful Derbyshire dwelling in Two Dales, offers easy access to the Peak District National Park, Matlock, and Bakewell, all within a short driving distance.
This reverse-level, 105 square metre holiday home sleeps four, boasting two bedrooms, a well-equipped kitchen with dishwasher, and an enclosed front yard; nearby pubs and shops add to its convenience.
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 ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This Victorian terraced house at Lime Grove Walk 11 in Matlock offers a family-friendly base within 300 meters of the town centre and provides convenient access to the Peak District National Park.
This two-bedroom dwelling accommodates up to four guests with a farmhouse-style kitchen, a sitting room featuring a woodburning stove, and an enclosed rear garden with bike storage, ideal for exploring local attractions such as Hall Leys Park and Heights of Abraham.

Check Out Pet-Friendly Cottages in Chesterfield

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

2 Bedroom Accommodation In Chesterfield - Chesterfield
No reviews

2 Bedroom Accommodation In Chesterfield

cottage, Chesterfield
Cottage ∙ 1 Bedroom ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

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

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage

Search Luxury Cottages in Chesterfield

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

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Holymoorside

Popular Cottages with a Pool in Chesterfield

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

Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
9.8 95 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Ashover

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.

2 Bed In Chesterfield (Oc-49757) - Chesterfield
No reviews

2 Bed In Chesterfield (Oc-49757)

cottage, Upper Loads
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