Cottages in Chesterfield at the best prices

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Chesterfield cottages
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18 Best cottages in Chesterfield

Best family friendly Chesterfield cottage rentals

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

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
10 2 reviews
Chesterfield
18/09 – 24/09
$295/nighttotal: $1770 (6 )

Cottage ∙ 3 Bedrooms ∙ 6 Guests

3 2
cottage
This Peak District holiday home, located less than 1.6km from Matlock, offers easy access to attractions such as Gulliver's Kingdom (5.6km) and Bakewell (13.7km).
The 45 square metre, three-bedroom property sleeps six, boasting a multi-level layout with two lounges, a games room featuring table football and darts, and a secure storage area for bikes/motorbikes.
4 Lovely Cottages Situated In The Beautiful Derbyshire Village Of Barlow. - Chesterfield
Chesterfield
21/08 – 24/08
$486/nighttotal: $1458 (3 )

4 Lovely Cottages Situated In The Beautiful Derbyshire Village Of Barlow.

1 2
cottage , Barlow near Bakewell
This one-bedroom holiday let is located in Barlow, Derbyshire, on the edge of the Peak District National Park and approximately 16 kilometres from Sheffield.
This pet-friendly cottage accommodates up to three guests, offering Wi-Fi, private parking for two cars, and a patio, set within 81 hectares of woodland and pastures with eight fishing lakes.
Casa De Campo ∙ 2 Quartos ∙ 4 Hóspedes - Chesterfield
Chesterfield
18/09 – 24/09
$209/nighttotal: $1254 (6 )

Casa De Campo ∙ 2 Quartos ∙ 4 Hóspedes

2 2
cottage
Holly Cottage, a Grade II listed property dating from 1780, is located in Totley, Sheffield, on the edge of the Peak District National Park, approximately 17 kilometers from Chatsworth House and 16 kilometers from Bakewell.
This family-friendly holiday home sleeps 4 across 2 bedrooms, offering a character-rich interior with open beams, a woodburning stove, a well-equipped kitchen, and an enclosed courtyard, with easy access to local amenities and hiking routes.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
Chesterfield
18/09 – 24/09
$294/nighttotal: $1764 (6 )

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
cottage
This converted barn, offering a restful rural retreat, is located on the edge of the Peak District, 4.8 kilometres from Chatsworth House and a short drive from Bakewell.
This family-friendly cottage accommodates up to four guests across two bedrooms and one bathroom, featuring a well-equipped kitchen with a dishwasher, Wi-Fi, a garden with furniture, and private parking for two cars.

Best Chesterfield cottages with a kitchen

Cottage ∙ 3 Bedrooms ∙ 11 Guests - Chesterfield
Chesterfield
02/07 – 06/07
$587/nighttotal: $2348 (4 )

Cottage ∙ 3 Bedrooms ∙ 11 Guests

3 1
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
10 7 reviews
Chesterfield
21/08 – 24/08
$407/nighttotal: $1221 (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 ∙ 2 Guests - Chesterfield
Chesterfield
03/09 – 06/09
$309/nighttotal: $927 (3 )

Cottage ∙ 1 Bedroom ∙ 2 Guests

1 2
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.
Carr House Farm, Pet Friendly, With Open Fire In Wingerworth - Chesterfield
Chesterfield
03/09 – 06/09
$409/nighttotal: $1227 (3 )

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

3 2
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.

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.

Destinations nearby

Best Chesterfield cottage rentals with jacuzzi

Among the 18 accommodations in Chesterfield, here are the 4 best cottage rentals with a jacuzzi

The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe - Chesterfield
8.0 1 review
Chesterfield
03/09 – 06/09
$895/nighttotal: $2685 (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.
Cherry Tree Cottage, Pet Friendly, With Hot Tub In Chesterfield - Chesterfield
Chesterfield
21/08 – 24/08
$483/nighttotal: $1449 (3 )

Cherry Tree Cottage, Pet Friendly, With Hot Tub In Chesterfield

1 2
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.
The Olde Coach House - Cottage With Hot Tub - Chesterfield
9.9 106 reviews
Chesterfield
03/09 – 06/09
$494/nighttotal: $1482 (3 )

The Olde Coach House - Cottage With Hot Tub

3 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.
Highview Stables, Pet Friendly, With Hot Tub In Chesterfield - Chesterfield
Chesterfield
21/08 – 24/08
$470/nighttotal: $1410 (3 )

Highview Stables, Pet Friendly, With Hot Tub In Chesterfield

1 2
cottage , Chesterfield
Highview Stables, a self-catering property in Chesterfield, Derbyshire, is situated 0.5km from a pub and bus stop, and 5.3km from the nearest shop, offering easy access to the Peak District National Park and Chesterfield's historic town centre, including the Crooked Spire church.
This one-bedroom cottage boasts 90 square metres of floor space, accommodating up to four guests, and features a well-equipped kitchen, a jacuzzi, a garden, off-road parking for two cars, and a wood-burning stove in the sitting room.

Best pet friendly Chesterfield cottage rentals

Among the 18 accommodations in Chesterfield, here are the 4 best pet friendly cottage rentals

Overton - Chesterfield
Chesterfield
02/07 – 06/07
$286/nighttotal: $1144 (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 ∙ 3 Bedrooms ∙ 5 Guests - Chesterfield
Chesterfield
20/06 – 27/06
$188/nighttotal: $1316 (7 )

Cottage ∙ 3 Bedrooms ∙ 5 Guests

3 2
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.
Cottage ∙ 5 Bedrooms ∙ 9 Guests - Chesterfield
Chesterfield
03/09 – 06/09
$742/nighttotal: $2226 (3 )

Cottage ∙ 5 Bedrooms ∙ 9 Guests

5 2
cottage , Bolsover
The Pantiles cottage is centrally located in Bolsover, Derbyshire, a short walk from Bolsover Castle and within easy reach of Chesterfield and Chatsworth House.
This five-bedroom holiday home sleeps nine adults and three children, boasting three bathrooms, a large kitchen-diner, multiple living areas including a snug with an open fire, a private garden, and ample roadside parking for four cars, plus modern amenities such as Smart TVs, Netflix, and Wi-Fi.
Smithy Cottage - Chesterfield
Chesterfield
21/08 – 24/08
$310/nighttotal: $930 (3 )

Smithy Cottage

1 2
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.
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