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.

Peak District Escape | Business & Leisure Stay - Chesterfield
10 5 reviews

Peak District Escape | Business & Leisure Stay

apartment
This three-bedroom flat is centrally located in Chesterfield, providing immediate access to the town centre and situated within 500 meters of shops, restaurants, and local amenities.
This accommodation offers parking, internet, a kitchen, and space for up to six guests, making it suitable for contractors and business travellers needing a comfortable base for short or extended stays.
Stylish Flat In Chesterfield Peak District - Chesterfield
9.3 50 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.
Spire Haven - Chesterfield
9.9 23 reviews

Spire Haven

house, Chesterfield
Spire Haven is a holiday home located in Chesterfield, just 19 kilometres from Chatsworth House, 24 kilometres from Utilita Arena Sheffield, and 31 kilometres from Clumber Park, offering a peaceful retreat close to popular attractions. This property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The home features four bedrooms and two bathrooms, providing ample space for families or groups of friends, spread across 145 square metres. Guests can enjoy a fully equipped kitchen, a comfortable seating area, a garden, free parking, and complimentary Wi-Fi, making it a convenient and relaxing choice for a stay in Chesterfield.
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.

Best Chesterfield holiday rentals with air conditioning

Stylish Home From Home - Chesterfield
9.1 24 reviews

Stylish Home From Home

house, Nether Edge
This Nether Edge dwelling is located approximately 8.5 kilometres from Utilita Arena Sheffield and within a 34-43 kilometre radius of Chatsworth House, Cusworth Hall, Clumber Park, and Belle Vue.
This 9 square metre property offers accommodation for 13 guests, featuring a kitchen with a fridge, microwave oven, and dishwasher, two bathrooms, and complimentary WiFi, with parking available.
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.
Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre - Chesterfield
9.2 22 reviews

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

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
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.

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.

Jewel Cottage - Chesterfield
9.6 392 reviews

Jewel Cottage

house, Matlock
Jewel Cottage is situated on the edge of the Peak District National Park, just a short walk from the Victorian Spa town of Matlock, 8km from Chatsworth House and a 30-minute drive from Hardwick Hall. This charming cottage has consistently received excellent ratings for its location, cleanliness, and overall experience.
Jewel Cottage offers 2 bedrooms and 1 bathroom across 20 square metres. Guests can enjoy a fully equipped kitchen, a garden, a terrace, free parking, and free WiFi, making it an ideal base for exploring the Peak District and the surrounding area.
Blue Sky Cottage - Chesterfield
9.0 74 reviews

Blue Sky Cottage

house, Matlock
Blue Sky Cottage is located in Matlock, just 14 kilometres from Chatsworth House and within a 48 kilometre radius of Buxton Opera House, FlyDSA Arena, Alton Towers, and Nottingham Castle. This well-rated cottage has received excellent reviews for its location, cleanliness, and overall experience.
The cottage has one bedroom and one bathroom, offering comfortable accommodation for two guests in a 48 square metre space. Enjoy modern amenities including free Wi-Fi, a flat-screen TV, a washing machine, a fully equipped kitchen, and a peaceful terrace with private parking.
The Long Hall 2 Bed Ground Floor Annexed Apartment - Sleeps 6 - Chesterfield
No reviews

The Long Hall 2 Bed Ground Floor Annexed Apartment - Sleeps 6

apartment, Chesterfield
Apartment to rent. You will be in Chesterfield.
Services and facilities: free parking, a kitchen and a barbecue.
Springwood Cottage - Chesterfield
9.9 264 reviews

Springwood Cottage

apartment, Holmesfield
Springwood Cottage is located in Holmesfield, just 16.1 km from Chatsworth House and 16.1 km from FlyDSA Arena, offering a peaceful escape from the hustle and bustle. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The self-catering apartment spans 48 square meters and comfortably accommodates up to 4 guests. It features a fully equipped kitchen, a terrace, a garden, and free private parking, making it an ideal choice for families or groups of friends exploring the Peak District.

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.

The Bungalowbarlow - Chesterfield
9.6 35 reviews

The Bungalowbarlow

house, Dronfield
The BungalowBarlow is located in Dronfield, just 19 km from FlyDSA Arena and 35 km from Buxton Opera House, offering a peaceful escape from city life. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The two-bedroom house spans 105 square meters and comfortably accommodates up to five guests. It comes equipped with a fully fitted kitchen, a garden, parking, internet access, and a range of amenities, making it perfect for families and groups looking to explore the Peak District.
The Pottery Flat Chesterfield Three Star Gold - Chesterfield
9.2 180 reviews

The Pottery Flat Chesterfield Three Star Gold

apartment, Chesterfield
The Pottery Flat Chesterfield Three Star Gold is located in Chesterfield, just 19 kilometres from Chatsworth House, a beautiful stately home with extensive gardens. This apartment has excellent user, location, and cleanliness ratings, making it a top choice for travellers.
The self-catering property is 125 square metres and has three bedrooms, accommodating up to five guests. It comes with a fully equipped kitchen, a garden, free Wi-Fi, and private parking, offering everything you need for a comfortable stay.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.9 12 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Barlow
Smithy Cottage is a charming two-bedroom holiday home situated just 4.2 kilometres from Chesterfield, offering easy access to the Derbyshire countryside and the National Park. The cottage is located near the Peacock at Barlow, a popular pub with a great menu, and Barlow also has a children's play area.
This 105 square metre property can accommodate up to four guests and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as a relaxing front yard, a private driveway, and complimentary Wi-Fi.
Lovely Apartment Above  Cafe Near Peak District - Chesterfield
9.7 305 reviews

Lovely Apartment Above Cafe Near Peak District

apartment
This charming apartment is located in Barlow, a picturesque village on the edge of the Peak District, just a 10-minute drive from Chatsworth House. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
This self-contained flat has one bedroom and one bathroom, comfortably accommodating two guests. Amenities include a private garden, parking, internet access, and a charming location above a 200-year-old cafe, offering a unique and historic setting.

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.

Artist-designed Japanese Loft With Home Cinema - Chesterfield
10 1 review

Artist-designed Japanese Loft With Home Cinema

apartment, Chesterfield
Little Fairfield - Chesterfield
9.4 7 reviews

Little Fairfield

apartment, Ashover
The Golden House, Spacious Family Home, Parking, Garden - Chesterfield
9.5 2 reviews

The Golden House, Spacious Family Home, Parking, Garden

house, Ecclesall
Ling Farm Cottage - Chesterfield
9.8 83 reviews

Ling Farm Cottage

house, Holmewood

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.

Old Barn Conversion Close To The Peak District - Chesterfield
9.7 299 reviews

Old Barn Conversion Close To The Peak District

apartment

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.

Yew Tree Cottage - Chesterfield
9.2 2 reviews

Yew Tree Cottage

house, Old Brampton
Rambler's Cottage - Chesterfield
9.3 12 reviews

Rambler's Cottage

house, Tansley
Blissful Barrys - Chesterfield
9.7 42 reviews

Blissful Barrys

apartment
Riber View Barn, Ashover - Chesterfield
No reviews

Riber View Barn, Ashover

apartment, Chesterfield

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.

40 M² House ∙ 2 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

40 M² House ∙ 2 Bedrooms ∙ 5 Guests

house, Matlock Bath
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
Velvet Residence Central Sheffield Parking 12ppl - Chesterfield
8.0 2 reviews

Velvet Residence Central Sheffield Parking 12ppl

apartment, Sheffield
Cottage ∙ 1 Bedroom ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage

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.

Kirkham House - Chesterfield
9.2 53 reviews

Kirkham House

house, Matlock
Wigley Farm House Cottage, Pet Friendly, With Hot Tub In Chesterfield - Chesterfield
No reviews

Wigley Farm House Cottage, Pet Friendly, With Hot Tub In Chesterfield

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

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
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