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.

Cuckoo Nest - Chesterfield
8.3 24 reviews
Chesterfield
04/07 – 05/07
£342/nightfor 1 night

Cuckoo Nest

1 2
house , Chesterfield
Cuckoo Nest, a self-catering house in Chesterfield, is situated approximately 13.8km from Chatsworth House and within a 37-55km radius of attractions including the Utilita Arena Sheffield, Buxton Opera House, and Nottingham Castle.
This one-bedroom property boasts 90 square metres of floor space, including a fully equipped kitchen with dishwasher, a private garden, free Wi-Fi, and private parking, ideal for couples seeking a peaceful retreat with opportunities for cycling nearby.
Matlock Glamping Rooms - Chesterfield
9.1 176 reviews
Chesterfield
07/07 – 08/07
£75/nightfor 1 night

Matlock Glamping Rooms

1 1
studio , Matlock
This studio apartment is located in Matlock, Derbyshire, just a short distance from the town centre and popular attractions like the Heights of Abraham and Matlock Bath. Guests have consistently rated it excellent for its location, cleanliness, and overall experience.
The studio is a comfortable and compact space, offering 18 square metres of living area and accommodating up to 6 guests. It includes a kitchen with a fridge, microwave oven, and free WiFi, as well as private parking for your convenience.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
Chesterfield
04/07 – 05/07
£480/nightfor 1 night

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
cottage
This Victorian terraced house at Lime Grove Walk 11 in Matlock offers a family-friendly base within 300 meters of the town centre and provides convenient access to the Peak District National Park.
This two-bedroom dwelling accommodates up to four guests with a farmhouse-style kitchen, a sitting room featuring a woodburning stove, and an enclosed rear garden with bike storage, ideal for exploring local attractions such as Hall Leys Park and Heights of Abraham.
Lovely Home Close To City Center & Rail Station - Chesterfield
9.2 78 reviews
Chesterfield
21/08 – 23/08
£207/nighttotal: £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.

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.

Little Manor - Chesterfield
8.5 52 reviews
Chesterfield
18/10 – 26/10
£85/nighttotal: £680 (8 )

Little Manor

2 5
house , Chesterfield
Little Manor is a sustainable holiday home located in Chesterfield, just 22 kilometres from Chatsworth House and 24 kilometres from FlyDSA Arena, offering a peaceful escape in a quiet neighbourhood. The property has received very good ratings for its cleanliness, location and overall experience.
The two-bedroom home comfortably sleeps four guests and features a well-equipped kitchen with a fridge, microwave and toaster. Guests can enjoy the outdoor space with a patio and garden, free parking and a terrace with views of the quiet street.
Moor Farm Cottage - Chesterfield
Chesterfield
26/09 – 27/09
£625/nightfor 1 night

Moor Farm Cottage

1 2
cottage , Chesterfield
This golf cottage in Chesterfield offers convenient access to local attractions, being situated within 10 km of Lumsdale Valley, Queen's Park, Crown Square, Grassmoor Country Park, and Hall Leys Park.
The property features a private hot tub, free WiFi, a well-equipped kitchen with a dishwasher and fridge, two bathrooms, and on-site parking, with a washing machine available for guest use.
Prime Location 2 Bed Parking Included - Chesterfield
10 2 reviews
Chesterfield
21/08 – 23/08
£129/nighttotal: £258 (2 )

Prime Location 2 Bed Parking Included

1 2
house , Chesterfield
This detached house is conveniently located in Chesterfield, 17.7 kilometres from Chatsworth House and 22.5 kilometres from Utilita Arena Sheffield.
This 88 square metre property accommodates up to 7 guests with 1 bedroom and 1 bathroom, offering free WiFi, a fully equipped kitchen with a dishwasher and oven, and dedicated parking.
Daniel’s Semi Rural Retreat - Chesterfield
8.7 63 reviews
Chesterfield
04/07 – 05/07
£100/nightfor 1 night

Daniel’s Semi Rural Retreat

2 2
apartment , Clowne
Daniel's Semi Rural Retreat, a self-catering apartment in Clowne, Derbyshire, offers easy access to Clumber Park (22.5km), Sherwood Forest (24km), Chatsworth House (30.5km), and Sheffield (29km).
This 74 square metre property features two bedrooms, one bathroom, sleeps five guests, and includes a garden, parking, Wi-Fi, a fully equipped kitchen with oven and microwave, and a washing machine.

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.

Fairfield Snug - Ashover Village Super King-twin - Chesterfield
9.6 8 reviews
Chesterfield
21/08 – 23/08
£86/nighttotal: £172 (2 )

Fairfield Snug - Ashover Village Super King-twin

1 2
apartment , Ashover
This recently renovated Ashover apartment is situated 17.7 kilometres from Chatsworth House and 32.2 kilometres from Utilita Arena Sheffield.
This 22 square metre flat offers accommodation for up to three guests, with a terrace, on-site parking, complimentary WiFi, and an on-site coffee shop for convenience.
Ranmoor Serviced Apartments At Wilkinson Lane - The Sandford Suite - Chesterfield
8.9 44 reviews
Chesterfield
21/08 – 23/08
£176/nighttotal: £352 (2 )

Ranmoor Serviced Apartments At Wilkinson Lane - The Sandford Suite

1 2
apartment , Sheffield
The Sandford Suite, a Ranmoor serviced apartment in Sheffield, is conveniently located 6.8km from the Utilita Arena and offers easy access to other attractions.
This one-bedroom flat provides comfortable accommodation for up to three guests, featuring a fully equipped kitchen with fridge, a private terrace/balcony, free Wi-Fi, private parking, and a washing machine.
Apartment ∙ 5 Bedrooms ∙ 12 Guests - Chesterfield
Chesterfield
27/06 – 04/07
£338/nighttotal: £2366 (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.
Amber Cabin - Chesterfield
9.7 3 reviews
Chesterfield
21/08 – 23/08
£170/nighttotal: £340 (2 )

Amber Cabin

2 2
cabin , Ashover
Amber Cabin, a self-catering lodge in Ashover, is situated 12.4 kilometres from Chatsworth House and 32.2 kilometres from Utilita Arena Sheffield.
This 70 square metre lodge accommodates up to 7 guests across 2 bedrooms and 2 bathrooms, featuring a garden, terrace, WiFi, and private parking, with a kitchen and living area with a fireplace.

Neighborhoods and points of interest in Chesterfield

Best Chesterfield holiday rentals with air conditioning

The Little Trout Cottage - Chesterfield
9.1 19 reviews
Chesterfield
26/06 – 28/06
£179/nighttotal: £358 (2 )

The Little Trout Cottage

1 4
apartment , Barlow
The Little Trout cottage is located in Barlow, North Derbyshire, offering easy access to the Peak District National Park.
This three-bedroom, one-bathroom property sleeps five, including one well-behaved dog, and boasts a kitchen, parking, and internet access.
Hip Hideaway In The Trendiest Part Of Town - Chesterfield
10 3 reviews
Chesterfield
07/07 – 08/07
£140/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.
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
£1119/nighttotal: £2238 (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.
Spacious 4 Bed Home For Families & Contractors. - Chesterfield
10 1 review
Chesterfield
21/08 – 23/08
£201/nighttotal: £402 (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.
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