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Chesterfield cottages
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26 Cottages at the best price in Chesterfield

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 ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

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

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, Inkersall
This Inkersall cottage, situated on the outskirts of Chesterfield, offers easy access to the Peak District National Park and is a short drive (distance unspecified) from Bolsover Castle.
The three-bedroom property sleeps five, features a well-equipped kitchen, utility room, private garden, and parking, providing comfortable accommodation for families or groups visiting Chesterfield and the surrounding area.

Best Chesterfield cottages with a kitchen

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.
Havendale - Chesterfield
No reviews

Havendale

cottage
This golfer's holiday home in Chesterfield is situated within a 15-minute walk of Mecca Bingo, Queen's Park, and Chesterfield Market, with Chesterfield Museum & Art Gallery and SMH Group Stadium also less than 2 km away.
This holiday cottage offers a kitchen with a dishwasher, complimentary Wi-Fi, a private garden, and free unassisted parking, with three bathrooms available for guest convenience.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage
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.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.8 20 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
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.

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. The weather is mild, the colours are stunning, and you'll avoid the crowds of summer. Plus, you'll be able to enjoy the local markets and events.
  • 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?

    You absolutely must see the Crooked Spire, the iconic landmark of Chesterfield. Don't miss the Chesterfield Museum, which tells the story of the town's history. And if you're a fan of nature, a trip to Queen's Park is a must.
  • 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?

    A cottage offers a unique and comfortable experience. You'll be able to relax and unwind in a peaceful setting, away from the hustle and bustle of the town. Plus, you'll be close to the beautiful countryside, perfect for exploring.
  • 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 very walkable. The town centre is compact, and you can easily explore the main attractions on foot. There are also plenty of cycle paths, making it easy 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 family-friendly activities are available in Chesterfield?

    Queen's Park is a great place for kids, with a playground, paddling pool, and plenty of space to run around. The Chesterfield Museum also has a family-friendly section with interactive exhibits.
  • What are the best pet friendly cottages in Chesterfield?

  • What are the best cottages with parking in Chesterfield?

Popular destinations

Best Chesterfield cottages with a jacuzzi

Among the 26 accommodations in Chesterfield, here are the 4 best cottages with a jacuzzi

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.
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.
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 ∙ 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.

Best pet friendly Chesterfield cottages

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

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.
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.
The Old Hayloft-uk39431 - Chesterfield
10 5 reviews

The Old Hayloft-uk39431

cottage, Dronfield
This one-bedroom apartment is situated in Dronfield, just a short distance from the Peak District National Park, offering easy access to stunning natural landscapes. It's also conveniently located near the city of Sheffield and the historic town of Chesterfield, making it a great base for exploring the region.
The self-catering property is ideal for couples or small families, with a comfortable king-size bed and a well-equipped kitchen. Enjoy the peace and quiet of the rural setting, with its 40-acre farm and over 30 horses, and take advantage of the private parking, internet access, and family-friendly amenities.
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.
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