Holiday Rentals in Chesterfield

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Chesterfield holiday rentals
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134 Holiday rentals and Airbnb in Chesterfield

Best family friendly Chesterfield holiday rentals

Among the 134 accommodations in Chesterfield, here are the 4 best family friendly rentals

Hanover Apartments - Stylish 1 Bedroom Suites, Sheffield City Centre - Hosted By Stay Host Save - Chesterfield
8.6 36 reviews
Chesterfield
21/08 – 23/08
155 €/nighttotal: 310 € (2 )

Hanover Apartments - Stylish 1 Bedroom Suites, Sheffield City Centre - Hosted By Stay Host Save

1 2
apartment , Sheffield
This apartment is located just 7km from the Utilita Arena Sheffield, offering a convenient base for exploring the city's attractions. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has one bedroom and one bathroom, covering 650 square metres. It comes equipped with a kitchen, a private bathroom, a terrace or balcony, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Oakleigh - Chesterfield
9.6 39 reviews
Chesterfield
26/09 – 27/09
356 €/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.
Peak Edge Home | Fast Wi-fi, Workspaces, 65" Tv! - Chesterfield
9.7 7 reviews
Chesterfield
18/10 – 26/10
151 €/nighttotal: 1208 € (8 )

Peak Edge Home | Fast Wi-fi, Workspaces, 65" Tv!

1 5
apartment , Derbyshire
This 2-bedroom flat offers a prime location on the outskirts of Chesterfield, placing you on the doorstep of the Peak District National Park and within easy reach of Chesterfield town centre, approximately 3.5 kilometers away.
This family-friendly property accommodates up to six guests with a fully equipped kitchen, super-fast Wi-Fi, a 65" TV, and both driveway and free street parking, making it ideal for exploring Derbyshire's natural beauty and local amenities.
2 Snape Hill - Chesterfield
9.5 46 reviews
Chesterfield
26/09 – 27/09
537 €/nightfor 1 night

2 Snape Hill

3 2
house , Dronfield
2 Snape Hill is a holiday home in Dronfield, just 14 km from FlyDSA Arena, 19 km from Chatsworth House, and 36 km from Clumber Park, making it a great base for exploring the Peak District. Guests consistently rate the property excellent for its location, cleanliness, and overall experience.
This three-bedroom property offers 130 square metres of space, comfortably accommodating up to six guests. The house has a fully equipped kitchen with a fridge, microwave, and dishwasher, a garden, parking, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

Best Chesterfield holiday rentals with parking

Apartment ∙ 5 Bedrooms ∙ 12 Guests - Chesterfield
Chesterfield
27/06 – 04/07
392 €/nighttotal: 2744 € (7 )

Apartment ∙ 5 Bedrooms ∙ 12 Guests

5 8
apartment
This five-bedroom detached house is located on Raynald Road, Great Britain, with convenient access to Sheffield city centre via the A57 and A61, and public transport options within walking distance.
This spacious accommodation, suitable for up to 12 guests, features a large open-plan living area, a fully equipped kitchen with a washer-dryer, private garden with BBQ, and driveway parking, offering flexible sleeping arrangements and self-check-in for a comfortable stay.
Ringinglow Cottage - Chesterfield
9.1 55 reviews
Chesterfield
08/08 – 09/08
174 €/nightfor 1 night

Ringinglow Cottage

1 2
house , Sheffield
Toy Cottage Sheffield is located on a quiet street in Sheffield, just 8.5 kilometres from Sheffield Train Station and 22.5 kilometres from Haddon Hall. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottage is a one-bedroom property with one bathroom, covering 23 square metres and accommodating up to two guests. It offers a fully equipped kitchen with a dishwasher, oven, and microwave, a terrace with quiet street views, and free private parking, making it perfect for a comfortable and convenient stay in Sheffield.
Excellent Studio Balcony Apartment In Sheffield - Chesterfield
9.1 102 reviews
Chesterfield
07/07 – 08/07
98 €/nightfor 1 night

Excellent Studio Balcony Apartment In Sheffield

1 1
studio , Sheffield
This Sheffield studio apartment, located approximately 6.3km from the Utilita Arena, offers convenient access to the city's attractions.
The self-contained flat sleeps up to 5 guests and features a kitchenette with microwave and fridge, free Wi-Fi, on-site parking, and a private balcony.
Havendale, Chesterfield - Chesterfield
Chesterfield
18/10 – 26/10
344 €/nighttotal: 2752 € (8 )

Havendale, Chesterfield

4 5
apartment , Chesterfield
This Chesterfield flat is located in Derbyshire, a short drive from the Peak District National Park and Chatsworth House, and within easy reach of historic sites like the 'Crooked Spire' church, Hardwick Hall, and Bolsover Castle.
This property offers four bedrooms for up to six guests, a well-equipped kitchen with a washer/dryer, a living space with a Smart TV and woodburning stove, and an enclosed garden with barbecue facilities, plus off-road parking and a bath lift available on request.

Frequently asked questions about holiday rentals in Chesterfield

  • Which neighborhood in Chesterfield should you consider for a vacation rental?

    The town centre is great for exploring, but for a quieter stay, look at properties near Queen's Park. It's a lovely green space, perfect for a relaxing stroll.
  • What are the best Airbnb and holiday rentals in Chesterfield?

  • What are the top family-friendly attractions in Chesterfield?

    The Chesterfield Canal is a great place for a family walk or bike ride. And for a fun day out, the Chesterfield Museum & Art Gallery has plenty to keep kids entertained.
  • What are the most popular Airbnbs in Chesterfield?

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

    It depends what you're after. If you want to catch the Chesterfield Festival, you'll need to book well in advance. Otherwise, you can usually find good deals outside of peak season.
  • 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.

  • What events or festivals should visitors check out in and around Chesterfield?

    The Chesterfield Festival is a big one, and the Bakewell Show is a good day out for the whole family. If you're here in December, the Christmas Market is a festive treat.
  • What are the best rentals for families and kids in Chesterfield?

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

    The Chesterfield Canal towpath is free to walk or cycle, and the Queen's Park is a great place for a picnic. You can also visit the Chesterfield Museum & Art Gallery for free.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?

    The best vacation 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.

  • Are there pet-friendly attractions in Chesterfield?

    Queen's Park is dog-friendly, and many pubs and restaurants in the town centre welcome well-behaved dogs. You can also walk the Chesterfield Canal towpath with your furry friend.
  • What are the benefits of choosing a vacation rental in Chesterfield?

    You'll have more space and privacy than a hotel, and you can often save money, especially if you're travelling with a family or group. Plus, you'll get a more authentic experience of the town.
  • What are the top sports attractions and facilities in Chesterfield?

    The Proact Stadium is home to Chesterfield FC, and there are several golf courses in the area, including the Chesterfield Golf Club. The Queen's Park has a great playground for kids.

Destinations nearby

Best Chesterfield holiday rentals with a balcony

The Carriage - Chesterfield
10 1 review
Chesterfield
21/08 – 23/08
123 €/nighttotal: 246 € (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.
Springwood Barn No1 Forest - Chesterfield
9.9 8 reviews
Chesterfield
26/06 – 28/06
334 €/nighttotal: 668 € (2 )

Springwood Barn No1 Forest

2 4
house , Holmesfield
Springwood Barn No1, a self-catering property in Holmesfield, is situated 15.1 km from Chatsworth House and 16.1 km from the FlyDSA Arena.
This one-bedroom house offers 63 square metres of space, sleeping up to 7 guests and boasting two bathrooms, a private garden with terrace, free parking, and Wi-Fi.
1 Coach House Mews - Matlock Bath - Chesterfield
9.6 215 reviews
Chesterfield
07/07 – 08/07
209 €/nightfor 1 night

1 Coach House Mews - Matlock Bath

2 1
apartment , Matlock Bank
This apartment is located in the quiet district of Matlock Bank, just 10 miles from Chatsworth House and 22 miles from Buxton Opera House, making it an ideal base for exploring the Peak District. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property offers two bedrooms and two bathrooms, providing comfortable accommodation for up to four guests. The 70 square metre apartment features a fully equipped kitchen, a terrace with inner courtyard views, free parking, and free Wi-Fi, allowing you to relax and enjoy your stay.
Little Fairfield - Chesterfield
8.0 1 review
Chesterfield
07/07 – 08/07
115 €/nightfor 1 night

Little Fairfield

1 1
apartment , Ashover
This Ashover flat, located at Little Fairfield, is 17.7 kilometres from Chatsworth House and 32.2 kilometres from Utilita Arena Sheffield, with Clumber Park and Sherwood Forest also within a 38.6 kilometre radius.
This compact 18 square metre studio apartment accommodates two guests with one bedroom and one bathroom, offering complimentary high-speed WiFi, a kitchenette, and free on-site parking.

Best Chesterfield holiday rentals with air conditioning

Spacious 4 Bed Home For Families & Contractors. - Chesterfield
10 1 review
Chesterfield
21/08 – 23/08
233 €/nighttotal: 466 € (2 )

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.
Hip Hideaway In The Trendiest Part Of Town - Chesterfield
10 3 reviews
Chesterfield
07/07 – 08/07
162 €/nightfor 1 night

Hip Hideaway In The Trendiest Part Of Town

2 1
house , Nether Edge
This Nether Edge property is located 7.7 kilometres from Utilita Arena Sheffield and 20.9 kilometres from Chatsworth House.
This two-bedroom holiday cottage accommodates up to six guests and offers a kitchen with a fridge and microwave, air conditioning, a terrace, garden, and on-site parking.
Small 1 Bed Apartment - Free Parking!!! - Chesterfield
8.8 12 reviews
Chesterfield
21/08 – 23/08
122 €/nighttotal: 244 € (2 )

Small 1 Bed Apartment - Free Parking!!!

1 2
apartment , Victoria
This stylish one-bedroom apartment is conveniently located off City Road in Victoria, approximately 5.5km from the FlyDSA Arena and within a 30-50km radius of attractions including Chatsworth House, Eco-Power Stadium, Clumber Park, and Cusworth Hall.
The 30-square-metre flat offers a private entrance, free Wi-Fi, parking, and sleeps up to five guests, boasting a fully equipped kitchen, air conditioning and a comfortable living area.
Riber Hall - Chesterfield
9.6 107 reviews
Chesterfield
08/08 – 09/08
3255 €/nightfor 1 night

Riber Hall

6 2
house , Matlock Bank
Riber Hall is located in Matlock Bank, Derbyshire, just 12 miles from Chatsworth House and 23 miles from Buxton Opera House, making it an ideal base for exploring the Peak District. The property has received excellent ratings for user experience, location, and cleanliness.
This six-bedroom, six-bathroom home offers 30 square metres of space, perfect for large families or groups. Guests can enjoy a private patio with an outdoor fireplace, a terrace with garden views, a hot tub, a fully equipped kitchen, and a tranquil garden.
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