Holiday Rentals in Chesterfield

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Chesterfield holiday rentals
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Best Holiday rentals and Airbnb offers in Chesterfield

Search Holiday Rentals near the Heart of the City in Chesterfield

Reconnect with your partner at secluded holiday rentals for couples in Chesterfield, offering intimate settings for a city break.

Stylish Flat In Chesterfield Peak District - Chesterfield
9.3 51 reviews

Stylish Flat In Chesterfield Peak District

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.
The Corner House C-town Centre 2 Bedroom Apartment - Chesterfield
9.7 59 reviews

The Corner House C-town Centre 2 Bedroom Apartment

apartment
This newly renovated ground floor flat is located just a short walk from Chesterfield town centre and train station, making it ideal for exploring the Peak District National Park, which is easily accessible from the property. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The flat has two bedrooms, accommodating up to four guests, making it perfect for families or groups of friends. It features a fully equipped kitchen, a small courtyard, designated workspaces, and super-fast fibre broadband, ensuring a comfortable and convenient stay.
Spire View | Chesterfield 2 Bedroom Apartment - Chesterfield
9.9 19 reviews

Spire View | Chesterfield 2 Bedroom Apartment

apartment
This Chesterfield apartment, situated a short walk from Chesterfield railway station and the town centre, offers easy access to the Peak District National Park.
The two-bedroom flat, formerly a dance academy, features an open-plan living space with workspace, a fully equipped kitchen, and accommodates up to four guests; nearby paid parking is available from £3 per 24 hours.
Lv8 Chesterfield - Chesterfield
9.6 5 reviews

Lv8 Chesterfield

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.

Best Chesterfield holiday rentals with air conditioning

The Urban Residence - Sheffield 6br Group-family Stay - Sleeps 12 - Chesterfield
No reviews

The Urban Residence - Sheffield 6br Group-family Stay - Sleeps 12

house, Victoria
The Urban Residence is a spacious six-bedroom flat located in the Sheffield district of Victoria, offering convenient access to local attractions.
This family-friendly apartment provides accommodation for up to 12 guests, featuring a private terrace, free WiFi, complimentary private parking, and a car rental service on-site.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 7 reviews

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

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.
The Little Trout Cottage - Chesterfield
9.2 24 reviews

The Little Trout Cottage

apartment
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
9.6 7 reviews

Hip Hideaway In The Trendiest Part Of Town

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.

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.

Popular destinations

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.

Sheffield City Centre Apartment & Balcony - Chesterfield
9.7 208 reviews

Sheffield City Centre Apartment & Balcony

apartment, Sheffield
This Sheffield city centre flat is located less than 0.6km from the city centre, 6.4km from the Utilita Arena, and between 26 and 42km from Chatsworth House, Eco-Power Stadium, Cusworth Hall, and Buxton Opera House.
The 54 square metre apartment offers two bedrooms, one bathroom, sleeps four guests, and includes a private balcony, secure parking, a well-equipped kitchen, and free Wi-Fi.
Deluxe City Centre Studio Apartment With Balcony & City Views - Free Wifi Netflix, Gym Access - Westone - Chesterfield
9.3 153 reviews

Deluxe City Centre Studio Apartment With Balcony & City Views - Free Wifi Netflix, Gym Access - Westone

studio, Sheffield
This West One studio apartment enjoys a central Sheffield location, just 0.8 kilometres from the city centre and 6.4 kilometres from the Utilita Arena.
The self-contained flat offers a private balcony with city views, sleeps five guests, includes a fully equipped kitchen, free Wi-Fi, Netflix, and access to a gym.
3bdr Modern Home In Sheffield And Free Parking With Balcony - Chesterfield
No reviews

3bdr Modern Home In Sheffield And Free Parking With Balcony

house, Heeley
This 3-bedroom modern detached house is located in Sheffield's Heeley district, offering convenient access to local amenities and attractions.
This spacious property, covering 120 square meters, accommodates up to 11 guests and features complimentary on-site parking, free high-speed WiFi, a fully equipped kitchen, and a private balcony.
Studio 77 - Stylish, Parking, Wi-fi, Netflix - Chesterfield
9.4 62 reviews

Studio 77 - Stylish, Parking, Wi-fi, Netflix

studio, Sheffield
Studio77 Sheffield is situated 5 kilometres from the Utilita Arena Sheffield, offering convenient access by car to Chatsworth House, Clumber Park, and Cusworth Hall.
This 25 square metre studio flat sleeps two guests and features a fully equipped kitchen, terrace, garden, free parking, and free Wi-Fi.

Neighborhoods and points of interest 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.

2 Bed Stylish Apartment Close 2 City Centre & Rail Station - Chesterfield
No reviews

2 Bed Stylish Apartment Close 2 City Centre & Rail Station

apartment, Sheepbridge and Whittington Moor Station
This spacious 140 square meter flat is located in Sheepbridge and Whittington Moor Station, offering excellent transport links to Sheffield city centre and the rail station, with Sheffield city centre being 3.7 kilometers away.
This one-bedroom flat accommodates up to 7 guests with two bathrooms, a fully equipped kitchen including a fridge and microwave oven, and complimentary WiFi, making it ideal for both leisure and business stays.
Kedleston Cottage - Darwin Lake Holiday Village - Chesterfield
8.3 9 reviews

Kedleston Cottage - Darwin Lake Holiday Village

house, Matlock
Kedleston Cottage, a three-bedroom house sleeping 14, is situated in Matlock, Derbyshire, approximately 11.7km from Chatsworth House and within easy driving distance of Buxton and Sheffield.
This self-catering property boasts three bathrooms, parking, a garden, and sun terrace, offering access to fishing and hiking in the Peak District National Park.
The Rumblings 1 - Chesterfield
8.7 27 reviews

The Rumblings 1

house, Barlow
The Rumblings 1, a Barlow holiday home, offers peaceful accommodation within easy reach of Chatsworth House (11km), Utilita Arena Sheffield (21km), Buxton Opera House (32km), and Sherwood Forest (50km).
This 105 square metre property features two bedrooms, one bathroom, a fully equipped kitchen with fridge and microwave, free Wi-Fi, private parking, and accommodates up to four guests, plus one well-behaved dog; nearby cycling is also available.
The Rumblings 3, Barlow - Chesterfield
No reviews

The Rumblings 3, Barlow

apartment, Dronfield
This end-of-terrace cottage, located 1 kilometre from Barlow village near Chesterfield, offers a convenient base for exploring the Peak District and is within easy reach of attractions such as Chatsworth House and Sheffield City Hall.
This family-friendly accommodation sleeps up to five guests in two bedrooms, featuring a king-size double and a second-floor family room with three single beds, a woodburner in the open-plan living area, a dedicated playroom, and off-road parking for one car.

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.

Detached 3br Bungalow | 15 Mins To Peak District - Chesterfield
10 26 reviews

Detached 3br Bungalow | 15 Mins To Peak District

apartment
6 Single Beds | Parking | Long Stay Deal | 3br - Chesterfield
No reviews

6 Single Beds | Parking | Long Stay Deal | 3br

apartment, Sheffield
Manor House - Chesterfield
9.6 103 reviews

Manor House

house, Chesterfield
3 Bedroom House Near Woodland - Chesterfield
9.5 11 reviews

3 Bedroom House Near Woodland

house

Browse Luxury Holiday Rentals in Chesterfield

Staying in a luxury holiday rental or Airbnb in Chesterfield ensures every detail of your trip feels considered. Enjoy high-end finishes and prime locations.

2 Bed In Holmesfield Oc-pk783 - Chesterfield
10 1 review

2 Bed In Holmesfield Oc-pk783

house, Dronfield

Find the Best Dog-Friendly Self-Catering Rentals in Chesterfield

No need to leave your dog behind in Chesterfield. Our holiday rentals offer proximity to dog parks and lovely city walks.

2 Bed House - Near Central Sheffield - Fast Wi-fi - Chesterfield
9.9 7 reviews

2 Bed House - Near Central Sheffield - Fast Wi-fi

apartment, Sheffield
The Loft At The George - Chesterfield
9.0 41 reviews

The Loft At The George

house, Chesterfield
Chatsworth Terrace - Chesterfield Centre And Peak District - Chesterfield
8.7 3 reviews

Chatsworth Terrace - Chesterfield Centre And Peak District

house, Chesterfield
Charming 18th Century Stone Cottage - Chesterfield
9.9 42 reviews

Charming 18th Century Stone Cottage

apartment

Choose the Right Holiday Rentals with a Pool in Chesterfield

Choosing a holiday rental in Chesterfield with a pool allows for a proper swim in the heart of the city. Browse our available options.

900 M² House ∙ 4 Bedrooms ∙ 7 Guests - Chesterfield
No reviews

900 M² House ∙ 4 Bedrooms ∙ 7 Guests

house
Open Haven Collective With Man Cave And Parking 10ppl - Chesterfield
9.3 3 reviews

Open Haven Collective With Man Cave And Parking 10ppl

house, Handsworth
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 47 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
Velvet Residence Central Sheffield Parking 12ppl - Chesterfield
8.0 2 reviews

Velvet Residence Central Sheffield Parking 12ppl

apartment, Sheffield

Compare Self-Catering Rentals with a Hot Tub in Chesterfield

A hot tub to come back to after a day in Chesterfield changes the whole feel of a stay. These holiday rentals are ready for you. Choose the one that suits you best.

Highgate House - Chesterfield
No reviews

Highgate House

house, Dronfield
Wigley Farm House Cottage - Chesterfield
10 7 reviews

Wigley Farm House Cottage

apartment
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Bolsover
Belgrano - Chesterfield
8.9 10 reviews

Belgrano

house, Matlock
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