Holiday Rentals in Chesterfield

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Chesterfield holiday rentals
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Best Holiday rentals and Airbnb offers in Chesterfield

Best Holiday Rentals for Families in Chesterfield

Family holidays in Chesterfield work best when your holiday rental is properly set up with space and city attractions within easy reach.

Garland Way 2 Bed House Sheffield Free Parking 5 Min From M1 - Chesterfield
8.1 35 reviews
Chesterfield
03/09 – 06/09
£112/nighttotal: Â£336 (3 )

Garland Way 2 Bed House Sheffield Free Parking 5 Min From M1

2 2
house , Mosborough
This two-bedroom house in Mosborough, Sheffield, is situated a 5-minute drive (8km) from the M1 motorway and 12.4km from the Utilita Arena Sheffield.
The property offers free private parking, Wi-Fi, a fully equipped kitchen with dishwasher, a garden, and accommodates up to seven guests; enjoy easy access to the M1 for exploring Yorkshire.
The Little Red House - Chesterfield
9.6 88 reviews
Chesterfield
08/08 – 09/08
£135/nightfor 1 night

The Little Red House

2 2
apartment , Sheffield
The Little Red House is a comfortable apartment located in Sheffield, just a short drive from attractions like FlyDSA Arena, Clumber Park, and Eco-Power Stadium. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy a private garden and terrace, a fully equipped kitchen with a dishwasher, a washing machine, and free Wi-Fi and parking.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 5 reviews
Chesterfield
03/09 – 06/09
£179/nighttotal: Â£537 (3 )

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
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.
Poppy Cottage - Chesterfield
9.4 65 reviews
Chesterfield
03/09 – 06/09
£171/nighttotal: Â£513 (3 )

Poppy Cottage

2 2
house , Matlock
Poppy Cottage is a charming house in Matlock, just 14 kilometres from Chatsworth House and 35 kilometres from Buxton Opera House, offering a peaceful retreat away from the hustle and bustle. This property has consistently received excellent ratings for its cleanliness, location and overall user experience.
The house has two bedrooms and one bathroom across 52 square metres of living space. Guests can enjoy a fully equipped kitchen, a comfortable living area with a flat-screen TV, free Wi-Fi, on-site parking, and a tennis court, making it perfect for families and groups seeking a relaxing and active getaway.

Top Holiday Rentals with Parking in Chesterfield

Free on-site parking comes with these holiday rentals in Chesterfield, allowing you to focus on the city centre from day one.

Stylish Flat In Chesterfield Peak District - Chesterfield
9.2 41 reviews
Chesterfield
21/08 – 23/08
£71/nighttotal: Â£142 (2 )

Stylish Flat In Chesterfield Peak District

1 2
apartment , Chesterfield
This Chesterfield apartment, situated in the Peak District, is conveniently located within a 21km radius of Chatsworth House, Clumber Park, and Buxton Opera House.
The 40 square metre flat offers one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen with microwave, private parking, and free Wi-Fi.
Oakleigh - Chesterfield
9.6 39 reviews
Chesterfield
08/08 – 09/08
£380/nightfor 1 night

Oakleigh

2 2
house , Old Brampton
This Old Brampton house, ideally located near Chatsworth House (13.2 km), offers easy access to major attractions including the Utilita Arena Sheffield (27.4 km) and Buxton Opera House (33.8 km).
The two-bedroom property provides free private parking, Wi-Fi, a dishwasher, and a garden, comfortably accommodating families or small groups seeking self-catering accommodation near Chatsworth House.
Lovely Home Close To City Center & Rail Station - Chesterfield
9.2 78 reviews
Chesterfield
21/08 – 23/08
£207/nighttotal: Â£414 (2 )

Lovely Home Close To City Center & Rail Station

2 2
apartment , Chesterfield
This comfortable apartment is situated in Chesterfield, just a short distance from the city centre and train station, making it easy to explore both the town and the surrounding attractions like FlyDSA Arena (25 km), Clumber Park (31 km), and Sherwood Forest (38 km). The apartment enjoys excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom, two-bathroom home offers 140 square metres of space, comfortably accommodating up to four guests. The apartment is equipped with a modern kitchen, including a fridge, freezer, microwave oven, and dishwasher, along with internet access and parking.
Contractor Friendly 3br Sleeps 5 - Chesterfield
Chesterfield
02/07 – 06/07
£119/nighttotal: Â£476 (4 )

Contractor Friendly 3br Sleeps 5

3 1
house , Duckmanton
This detached property is located in Duckmanton, 22 kilometers from Utilita Arena Sheffield and Clumber Park, with Chatsworth House 24 kilometers away.
This 80 square meter holiday home offers 3 bedrooms, 1 bathroom, and accommodates up to 5 guests, featuring a fully equipped kitchen, free Wi-Fi, and private parking.

Frequently asked questions about holiday rentals in Chesterfield

  • When is the best time to book a vacation rental in Chesterfield?

    Chesterfield is lovely all year round, but if you want to avoid the crowds, try booking outside of the school holidays. May and September are usually good months for a visit, the weather is still pleasant and there's plenty going on.
  • What are the best Airbnb and holiday rentals in Chesterfield?

  • What are the best budget-friendly activities in Chesterfield?

    Take a walk along the Chesterfield Canal towpath, it's free and you can see some beautiful scenery. Visit the Chesterfield Market, it's a great place to pick up some souvenirs and local produce. And don't forget to check out the free exhibitions at the Chesterfield Museum and Art Gallery.
  • What are the most popular Airbnbs in Chesterfield?

  • What are the best walking or cycling routes in Chesterfield?

    The Chesterfield Canal towpath is a great option for a leisurely walk or cycle. For something a bit more challenging, try the High Peak Trail, which runs for 17 miles through the Derbyshire countryside. And if you're looking for a shorter route, the Chesterfield town centre is very walkable, with plenty of interesting shops and buildings to see.
  • What are the best holiday rentals with a pool in Chesterfield?

    Manor House, Family Fun Party House Pool - Bar - Sauna - Cinema and Tawny Owl Barn are the best holiday rentals with a pool in Chesterfield.

  • Are there pet-friendly attractions in Chesterfield?

    The Chesterfield Canal towpath is great for a walk with your dog. Many pubs and cafes in Chesterfield are also dog-friendly. You can also check out the Chesterfield Museum and Art Gallery, they have a special 'doggy day' once a month.
  • What are the best rentals for families and kids in Chesterfield?

  • What are the benefits of choosing a vacation rental in Chesterfield?

    Vacation rentals offer more space and privacy than a hotel room. They're also often more affordable, especially if you're travelling with a family or a group of friends. And you can often find rentals with unique features, like a garden or a hot tub.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?

    The best holiday rentals or Airbnb with a jacuzzi in Chesterfield are Spahome With Hottub Sauna Bbq & Pool Table, Hot Tub House Close To Woodland And Peak District and Manor House.

Destinations nearby

Check Out Holiday Rentals with a Balcony in Chesterfield

Choosing a holiday rental in Chesterfield with a private balcony offers city skyline views that are worth every penny. Compare options and find yours.

The Carriage - Chesterfield
10 1 review
Chesterfield
21/08 – 23/08
£106/nighttotal: Â£212 (2 )

The Carriage

1 2
apartment , Matlock
This Matlock flat is located 7.2 kilometres from Chatsworth House and offers convenient access to Sheffield and Nottingham.
This one-bedroom flat, covering 12 square metres, accommodates up to three guests and features a kitchen, terrace, and complimentary Wi-Fi, with free private parking available.
The Olde Coach House - Chesterfield
8.3 11 reviews
Chesterfield
03/09 – 06/09
£264/nighttotal: Â£792 (3 )

The Olde Coach House

3 2
house , Chesterfield
The Olde Coach House is a tranquil retreat located 19 kilometres from Chatsworth House, offering a peaceful escape from the hustle and bustle of Chesterfield town. The property has received excellent ratings for its cleanliness, location, and overall user experience.
This 3-bedroom, 2-bathroom property spans 120 square metres and can comfortably accommodate up to 11 guests. Enjoy a range of on-site amenities including a fitness centre, tennis court, and a Jacuzzi, as well as a well-equipped kitchen, a spacious garden, and a terrace for outdoor dining.
The Carriage House - Chesterfield
9.3 104 reviews
Chesterfield
21/08 – 23/08
£135/nighttotal: Â£270 (2 )

The Carriage House

1 2
apartment , Matlock
The Carriage House is a charming apartment in Matlock, just 16km from Chatsworth House, 35km from Buxton Opera House, and 38km from Alton Towers. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment has one bedroom, one bathroom, and can accommodate up to two guests in its 25 square metres of space. It comes equipped with free Wi-Fi, a fully equipped kitchen, and a private terrace with garden views, allowing guests to enjoy a comfortable and convenient stay.
Stay@chesterfield - Chesterfield
9.5 36 reviews
Chesterfield
03/09 – 06/09
£105/nighttotal: Â£315 (3 )

Stay@chesterfield

3 2
house , Wingerworth
Stay@Chesterfield, a holiday home in Wingerworth, Derbyshire, is conveniently located approximately 19 kilometres from Chatsworth House, 32 kilometres from Clumber Park, and 40 kilometres from Sherwood Forest.
This 80 square metre property boasts three bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen with dishwasher, free Wi-Fi, private parking, and a terrace/garden.

Neighborhoods and points of interest in Chesterfield

Best Chesterfield holiday rentals with air conditioning

Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre - Chesterfield
9.2 25 reviews
Chesterfield
02/07 – 06/07
£331/nighttotal: Â£1324 (4 )

Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre

3 1
apartment , Sheffield
This recently renovated three-bedroom flat is ideally located just 2.6 kilometers from the FlyDSA Arena, close to fast-food restaurants, a supermarket, and the city centre. It has received excellent ratings for location, cleanliness, and user experience.
The apartment spans 105 square meters and includes a fully equipped kitchen, a comfortable living area, and a private garden. Guests can enjoy amenities such as air conditioning, free Wi-Fi, and private parking, making it a perfect choice for families or groups of friends visiting Sheffield.
Lv8 Chesterfield - Chesterfield
Chesterfield
25/06 – 16/07
£279/nighttotal: Â£5859 (21 )

Lv8 Chesterfield

1 2
apartment , Chesterfield
This one-bedroom flat in Chesterfield offers proximity to Chatsworth House (16 kilometres) and Utilita Arena Sheffield (22.5 kilometres), with East Midlands Airport 56 kilometres away.
This 55 square metre apartment accommodates two guests and features a fully equipped kitchen with a dishwasher, complimentary Wi-Fi, air conditioning, and private parking.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 8 reviews
Chesterfield
03/09 – 06/09
£1047/nighttotal: Â£3141 (3 )

Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise

3 2
house , Sheffield
This charming house is situated just 4 kilometres from the FlyDSA Arena, offering a peaceful retreat on a quiet street in Sheffield. The house has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property spans 150 square metres and comfortably accommodates up to 5 guests across 3 bedrooms and 1 bathroom. Enjoy the peaceful garden views, relax in the air-conditioned home, and make use of the fully equipped kitchen, picnic area, and free parking.
Spacious 4 Bed Home For Families & Contractors. - Chesterfield
10 1 review
Chesterfield
03/09 – 06/09
£206/nighttotal: Â£618 (3 )

Spacious 4 Bed Home For Families & Contractors.

4 2
house , Sheffield
This detached house is located in a residential district of Sheffield, offering convenient access to local amenities and transport links, with the city centre approximately a 15-minute drive away.
This spacious 105 square meter property features 4 bedrooms, 3 bathrooms, free Wi-Fi, private parking, and a fully equipped kitchen, accommodating up to 12 guests.
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