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

Oakleigh - Chesterfield
9.6 39 reviews
Chesterfield
08/08 – 09/08
440 €/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.
Modern 3 Bedroom Home, Close To City Centre And Peak District - Chesterfield
8.3 35 reviews
Chesterfield
03/09 – 06/09
148 €/nighttotal: 444 € (3 )

Modern 3 Bedroom Home, Close To City Centre And Peak District

3 2
house , Heeley
This modern Heeley house is situated near Sheffield city centre, offering easy access to the Peak District National Park within a 40-kilometre radius.
The 120-square-metre property boasts three bedrooms, one bathroom, sleeps nine guests, and includes a private garden, terrace, parking, and free Wi-Fi.
Bobbin Cottage - Chesterfield
8.8 78 reviews
Chesterfield
08/08 – 09/08
1070 €/nightfor 1 night

Bobbin Cottage

3 2
house , Matlock
Bobbin Cottage, a three-bedroom house in Matlock, Derbyshire, is conveniently located 12.5km from Chatsworth House and 32km from Buxton Opera House.
This 130 square metre property offers self-catering facilities including a dishwasher and fridge, private parking, a garden, and accommodates up to six guests, plus one well-behaved dog.
Peak Edge Terrace (Derbyshire, Peak District) - Chesterfield
9.9 141 reviews
Chesterfield
21/08 – 23/08
162 €/nighttotal: 324 € (2 )

Peak Edge Terrace (Derbyshire, Peak District)

1 2
house , Derbyshire
Peak Edge Terrace is located on the eastern edge of the Peak District, just 15 kilometers from Chatsworth House and a 20-minute walk from Chesterfield, offering a peaceful retreat in a beautiful setting. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The house comfortably accommodates up to six people with two bedrooms, a bathroom, a spacious living room, and a dedicated games room. Guests can enjoy a fully equipped kitchen, a private courtyard with garden furniture, and a range of amenities for both adults and children, including a Smart TV, board games, and access to local information.

Best Chesterfield holiday rentals with parking

1 Bed In Barlow 40971 - Chesterfield
9.0 2 reviews
Chesterfield
03/09 – 06/09
208 €/nighttotal: 624 € (3 )

1 Bed In Barlow 40971

1 2
house , Chesterfield
This one-bedroom holiday home in Barlow, Chesterfield, is situated 14km from Chatsworth House and 19km from the FlyDSA Arena.
The 45 square metre property features a fully equipped kitchen, private garden, free Wi-Fi, parking, and accommodates up to three guests.
The Bungalow@barlow, Pet Friendly, With Open Fire In Chesterfield - Chesterfield
10 1 review
Chesterfield
04/07 – 05/07
882 €/nightfor 1 night

The Bungalow@barlow, Pet Friendly, With Open Fire In Chesterfield

2 2
cottage , Dronfield
This charming cottage is situated just 3km from Chesterfield and 10km from the Peak District National Park, offering a peaceful retreat on the outskirts of Dronfield. It's consistently rated excellent by guests, making it a popular choice for travellers seeking a comfortable stay.
The cottage sleeps up to five guests in two bedrooms, perfect for families or groups of friends. It's equipped with modern amenities like a dishwasher and washing machine, plus a large garden with a patio and access to an orchard.
Derbyshire Holiday Cottages - Chesterfield
9.6 141 reviews
Chesterfield
07/07 – 08/07
113 €/nightfor 1 night

Derbyshire Holiday Cottages

2 1
house , Holmesfield
Derbyshire Holiday Cottages is a 2-bedroom house located in Holmesfield, a village in Derbyshire, just 14.5 kilometres from Chatsworth House and 17.7 kilometres from Utilita Arena Sheffield.
This family-friendly accommodation offers a peaceful garden, free parking, a fully equipped kitchen, free Wi-Fi, a flat-screen TV, and a terrace, with a maximum guest capacity of 7 people.
Smithy Cottage - Chesterfield
Chesterfield
04/07 – 05/07
488 €/nightfor 1 night

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.

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

Open Haven Collective With Man Cave And Parking 10ppl - Chesterfield
10 2 reviews
Chesterfield
02/07 – 06/07
232 €/nighttotal: 928 € (4 )

Open Haven Collective With Man Cave And Parking 10ppl

1 1
house , Handsworth
This detached house is located in Handsworth, 4.5 kilometres from the Utilita Arena Sheffield and 27 kilometres from Chatsworth House.
This property offers 79 square metres of living space with 3 bedrooms and 1 bathroom, accommodating up to 10 guests and featuring a 'Man Cave', a garden, and free private parking.
Stay@chesterfield - Chesterfield
9.5 36 reviews
Chesterfield
03/09 – 06/09
122 €/nighttotal: 366 € (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.
Matlock Town Centre Flat Near Transport Links - Chesterfield
8.6 6 reviews
Chesterfield
21/08 – 23/08
144 €/nighttotal: 288 € (2 )

Matlock Town Centre Flat Near Transport Links

1 2
apartment , Matlock
This Matlock town centre flat offers convenient access to transport links and is situated 12.4 km from Chatsworth House.
The 34-square-metre self-catering apartment features one bedroom, one bathroom, a balcony, and sleeps up to three guests, including children accompanied by a responsible adult.
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.

Best Chesterfield holiday rentals with air conditioning

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.
Riber Hall - Chesterfield
9.6 105 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.
The Stables East Lodge Country House - Chesterfield
8.1 17 reviews
Chesterfield
02/07 – 06/07
382 €/nighttotal: 1528 € (4 )

The Stables East Lodge Country House

3 1
house , Great Rowsley
This Peak District country retreat in Great Rowsley offers a peaceful escape, situated 6.1km from Chatsworth House and 26km from Buxton Opera House.
The 362 square metre property sleeps up to 13 guests, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, air conditioning, private parking, Wi-Fi, and a terrace with garden views.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 8 reviews
Chesterfield
21/08 – 23/08
1297 €/nighttotal: 2594 € (2 )

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.
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