Cottages in Chesterfield at the best prices

26 available cottage rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Chesterfield cottages
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

26 Best cottages in Chesterfield

Best family friendly Chesterfield cottage rentals

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

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.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chesterfield
9.8 16 reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, Old
Christmas Cottage, a three-storey stone house in Higham, Derbyshire, is situated near Ravensnest Wood and within easy driving distance (approximately 16km) of Matlock and the Peak District National Park.
This 130 square metre property sleeps five guests in three bedrooms (king-size, king-size, single with optional folding bed), features a fully equipped kitchen with dishwasher, a wood-burning stove, and a garden with barbecue; nearby attractions include Crich Tramway Village and the Heights of Abraham.
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.
40 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

40 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Matlock Bath
This pet-friendly holiday cottage is located in a rural area near Matlock, offering a peaceful retreat 2 kilometers from Matlock Bath.
This self-catering property spans 40 square meters, accommodating up to four guests in two double bedrooms and featuring a well-equipped kitchen, three bathrooms, a coal fire, private garden, and internet access.

Best Chesterfield cottages with a kitchen

Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, Bolsover
This 1930s art deco holiday home in Bolsover, Derbyshire, is conveniently located for exploring the region, with Sherwood Forest 48 kilometres away and the Peak District under 1 hour's drive.
This pet-friendly cottage accommodates up to five guests across three bedrooms and two bathrooms, featuring a dishwasher, two open fires, Wi-Fi, and a garden with seating and dining areas, with a travel cot, highchair, and stairgate available on request.
Carr House Farm, Pet Friendly, With Open Fire In Wingerworth - Chesterfield
No reviews

Carr House Farm, Pet Friendly, With Open Fire In Wingerworth

cottage, Chesterfield
Carr House Farm, a detached barn conversion near Wingerworth, sits on the edge of the Peak District, offering access to open moorland and wooded dales, with a shop 900 meters and a pub 800 meters away.
This spacious 130 square meter property accommodates six guests in three bedrooms, features an open-plan living area with a woodburning stove, a separate sitting room with a Smart TV, and provides off-road parking, a courtyard, and the option of two stables for horses.
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 ∙ 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.

Frequently Asked Questions about cottages in Chesterfield

  • What would be a good 2-days itinerary for visiting Chesterfield?

    On your first day, visit the Crooked Spire, have a look around Chesterfield Market, and maybe have a pint at a traditional pub like The Old House. On your second day, head to the Chesterfield Museum and Art Gallery, and then enjoy a walk along the canal in the afternoon.
  • What are the best cottage rentals in Chesterfield?

    Among the cottage rentals 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 Hasland, Staveley, and Brampton are popular for cottages, offering a quieter setting while still being close enough to the town centre.
  • What are the best cottage rentals with a pool in Chesterfield?

    The best cottage rental 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 lovely in Chesterfield, with mild weather and fewer crowds. You can enjoy the colours of the changing leaves and the blossoming spring flowers.
  • What are the best cottage rentals with a jacuzzi in Chesterfield?

    The best cottage rentals with a jacuzzi in Chesterfield are The Olde Coach House, Tawny Owl Barn and Boundary Cottage.

  • What are the can't-miss sights in Chesterfield?

    The Crooked Spire is a must-see, of course! The Chesterfield Museum and Art Gallery is worth visiting, and you can also explore the beautiful Queen's Park.
  • What are the best cottage rentals for families and kids in Chesterfield?

    The best cottage rentals 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 homely and comfortable experience than a hotel, and you can often find ones with lovely gardens and countryside views. They are also perfect for families or groups of friends.
  • What are the best pet friendly cottage rentals in Chesterfield?

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

    Yes, the town centre is compact and easily walkable. There are also bike paths along the canal and in Queen's Park, making it a great option for exploring the wider area.
  • What are the best cottage rentals with parking in Chesterfield?

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

    The restaurant at the Peak District Hotel has fantastic views of the surrounding countryside, and The Old Vicarage in Brampton offers a picturesque setting with a garden terrace.
  • What family-friendly activities are available in Chesterfield?

    Queen's Park has a playground, a boating lake, and a mini golf course. The Chesterfield Museum and Art Gallery has interactive exhibits for children, and the Chesterfield Canal is perfect for a leisurely stroll.

Popular destinations

Best Chesterfield cottage rentals with jacuzzi

Among the 26 accommodations in Chesterfield, here are the 2 best cottage rentals with a jacuzzi

Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
9.9 44 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage
The Gatehouse is a stone-built holiday home located in the small village of Teversal, just under 8 kilometres from the market town of Mansfield in Nottinghamshire. Situated on the grounds of the Grade II listed Teversal Manor, it offers a tranquil escape from the hustle and bustle of city life.
The cottage has four bedrooms, a games room, and multiple living spaces, comfortably accommodating up to eight guests. It features a private patio, a hot tub, a games room, and a fully equipped kitchen, making it ideal for families or groups of friends looking for a relaxing and enjoyable stay.
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.

Best pet friendly Chesterfield cottage rentals

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

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Morton
Naseby House, a stylish semi-detached property, is located in Morton, Derbyshire, 7.4 kilometres from Alfreton and conveniently close to the Peak District National Park.
This family-friendly cottage accommodates six guests across three bedrooms and offers a well-equipped open-plan living space, a separate snug, an enclosed private courtyard with barbecue, and roadside parking for two cars.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

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 ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
10 2 reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage
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.
Cedar Cottage - Chesterfield
No reviews

Cedar Cottage

cottage, Chesterfield
This Chesterfield cottage is situated 1.5km from the Barrow Hill Roundhouse Railway Museum, under 5km from Poolsbrook Country Park and the Technique Stadium, and less than 10km from Chesterfield Market and Mecca Bingo.
The self-catering holiday home offers free on-site parking, Wi-Fi in communal areas, two bathrooms, and allows pets; nearby attractions include outdoor activities at Poolsbrook Country Park and the football at the Technique Stadium.
©2026 cozycozy.com