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Chesterfield cottages
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18 Cottages at the best price in Chesterfield

Best family friendly Chesterfield cottages

Among the 18 accommodations in Chesterfield, here are the 4 best family friendly cottages

Courthouse Cottage, Eckington. - Chesterfield
Chesterfield
21/08 – 24/08
£209/nighttotal: £627 (3 )

Courthouse Cottage, Eckington.

2 2
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.
Cottage ∙ 3 Bedrooms ∙ 11 Guests - Chesterfield
Chesterfield
20/06 – 27/06
£180/nighttotal: £1260 (7 )

Cottage ∙ 3 Bedrooms ∙ 11 Guests

3 2
cottage
Pine Lodge, a Peak District National Park holiday home near Tansley, is situated 3.2km from the Crich Tramway Museum and under 16km from Chatsworth House.
This spacious lodge sleeps eleven guests in three bedrooms (plus two sofa beds), boasts two bathrooms, a fully equipped kitchen with dishwasher, private decking, parking for five cars, and offers Wi-Fi, plus a welcome pack.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.4 128 reviews
Chesterfield
03/09 – 06/09
£126/nighttotal: £378 (3 )

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
cottage
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.
1 Bedroom Accommodation In Dronfield - Chesterfield
10 1 review
Chesterfield
18/09 – 24/09
£72/nighttotal: £432 (6 )

1 Bedroom Accommodation In Dronfield

1 2
cottage , Dronfield
This one-bedroom apartment is situated in Dronfield, a town on the edge of the Peak District National Park, just 10km from Sheffield and 15km from Chesterfield, offering a peaceful escape from the city. The apartment is part of a converted barn on a 40-acre gated property with over 30 horses, perfect for a relaxing getaway.
The apartment has an open-plan living space ideal for two guests, with a well-equipped kitchen and comfortable sofas. Enjoy free WiFi, a dishwasher, a coffee machine, private parking for two cars, and easy access to local shops, restaurants, and attractions like the Peak District, Chesterfield, and the charming village of Hathersage.

Best Chesterfield cottages with a kitchen

Swallows Barn - Chesterfield
Chesterfield
21/08 – 24/08
£323/nighttotal: £969 (3 )

Swallows Barn

1 2
cottage , Chesterfield
This Chesterfield cottage, situated within 5km of Queen's Park, Mecca Bingo, St Mary and All Saints' Church, and 4.7km from Chesterfield Market, offers self-catering accommodation with free on-site parking and Wi-Fi in communal areas.
The property features two bathrooms, a fully equipped kitchen including a dishwasher, and a private garden; it's ideal for sporty travellers given its proximity to recreational facilities.
The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe - Chesterfield
8.0 1 review
Chesterfield
03/09 – 06/09
£478/nighttotal: £1434 (3 )

The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe

3 2
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.
Overton - Chesterfield
Chesterfield
04/07 – 08/07
£158/nighttotal: £632 (4 )

Overton

1 1
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 ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
Chesterfield
03/09 – 06/09
£396/nighttotal: £1188 (3 )

Cottage ∙ 4 Bedrooms ∙ 8 Guests

4 2
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.

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.

Destinations nearby

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 ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 7 reviews
Chesterfield
21/08 – 24/08
£217/nighttotal: £651 (3 )

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
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 ∙ 1 Bedroom ∙ 4 Guests - Chesterfield
9.7 11 reviews
Chesterfield
21/08 – 24/08
£271/nighttotal: £813 (3 )

Cottage ∙ 1 Bedroom ∙ 4 Guests

1 2
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 ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
Chesterfield
03/09 – 06/09
£290/nighttotal: £870 (3 )

Cottage ∙ 3 Bedrooms ∙ 6 Guests

3 2
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.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 47 reviews
Chesterfield
18/09 – 24/09
£136/nighttotal: £816 (6 )

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
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

Check Out Pet-Friendly Cottages in Chesterfield

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

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
Chesterfield
21/08 – 24/08
£141/nighttotal: £423 (3 )

Cottage ∙ 1 Bedroom ∙ 2 Guests

1 2
cottage
Stubley Hollow 6 is a charming cottage situated just 10km from the Peak District National Park, offering a peaceful escape from the city bustle. It's also conveniently located near Dronfield, a town with shops, restaurants and amenities.
This one-bedroom property can accommodate up to six guests and features a fully equipped kitchen with a dishwasher, a comfortable living space, and a bespoke bathroom. Guests can enjoy the rural setting, explore the Peak District, and even indulge in the equestrian activities on the 40-acre property.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
Chesterfield
21/08 – 24/08
£255/nighttotal: £765 (3 )

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
cottage , Barlow
This Barlow Country Park lodge is located in Barlow, South Yorkshire, on the edge of the Peak District National Park and close to the South Yorkshire border, offering 50 acres of pastures and woodland with 8 fishing lakes nearby.
This pet-friendly, family-friendly two-bedroom bungalow accommodates four guests, featuring an open-plan living space, a private garden, parking for two cars, and complimentary Wi-Fi, serving as a base for exploring the Peak District National Park.
The Olde Coach House - Cottage With Hot Tub - Chesterfield
9.9 106 reviews
Chesterfield
21/08 – 24/08
£263/nighttotal: £789 (3 )

The Olde Coach House - Cottage With Hot Tub

1 2
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 ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
Chesterfield
02/07 – 06/07
£115/nighttotal: £460 (4 )

Cottage ∙ 3 Bedrooms ∙ 6 Guests

3 1
cottage , Creswell
Oxcroft View, a three-bedroom Derbyshire holiday home in Oxcroft, is situated 3km from Clowne and within an hour's drive of Sheffield, Nottingham, and Chesterfield.
This pet-friendly Creswell cottage sleeps six, boasting a well-equipped kitchen, dining room, sitting room with wood-burning stove, family bathroom, cloakroom, and an external games room with pool table, table football, table tennis, and darts.
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