Holiday Rentals in Chesterfield

193 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Chesterfield holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.

College View - Chesterfield
9.8 16 reviews

College View

apartment
This Chesterfield studio apartment, a former dance studio, is centrally located, a short walk from Chesterfield railway station and the town centre, offering easy access to the Peak District National Park.
The self-contained apartment features a modern kitchen, two double beds sleeping up to four guests, fast broadband, and an open-plan living space, perfect for families or groups exploring Derbyshire.
The Blossoms - Studio Apartment - Chesterfield
9.6 45 reviews

The Blossoms - Studio Apartment

apartment
This Chesterfield studio apartment offers convenient ground-floor access and a private entrance, situated a short walk from Chesterfield railway station and the town centre, providing easy access to the Peak District National Park. This Derbyshire self-catering unit sleeps two guests and includes a well-equipped kitchenette with a fridge, microwave, kettle, toaster, and coffee press, plus a designated workspace and fast broadband.
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.
Modern 3 Bed Home, Chesterfield - Chesterfield
9.2 9 reviews

Modern 3 Bed Home, Chesterfield

apartment, Chesterfield
This modern 3-bedroom apartment is located in Chesterfield, just 21 kilometres from Chatsworth House and 22 kilometres from Utilita Arena Sheffield. It has received excellent ratings for location, cleanliness and overall experience.
The property is ideal for families or groups of up to nine guests, with a fully equipped kitchen, two bathrooms and free Wi-Fi. Guests can enjoy free parking on-site and have easy access to major attractions and transportation links.

Best Chesterfield holiday rentals with air conditioning

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.
Modern 3bedroom Home In The Heart Of Chesterfield - Chesterfield
8.8 5 reviews

Modern 3bedroom Home In The Heart Of Chesterfield

apartment
This Staveley flat offers convenient access to Sheffield city centre (12 kilometers), Meadowhall Shopping Centre (9 kilometers), the M1 motorway, and the Peak District National Park.
This 3-bedroom, 2-bathroom accommodation for up to 6 guests includes a fully equipped kitchen, free Wi-Fi, on-site parking, an EV charger, and a private garden.
Hip Hideaway In The Trendiest Part Of Town - Chesterfield
9.7 6 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.
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.

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.

 - Chesterfield
5.0 1 review

apartment, Nether Edge
This flat is located in the Nether Edge district, offering easy access to local amenities and transport links, with the city centre approximately 4 kilometers away.
This 45 square meter flat features one bedroom and one bathroom, accommodating up to three guests with internet, a kitchen, and a balcony, and is ideal for a quiet stay with a private host available.
The Carriage - Chesterfield
9.2 10 reviews

The Carriage

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.
Stay Angels - Hidden Gem - Chesterfield
8.3 26 reviews

Stay Angels - Hidden Gem

apartment, Nether Edge
This Nether Edge flat is situated 8.2km from the Utilita Arena Sheffield, offering easy access to attractions such as Chatsworth House (22.5km) and major airports.
The 50 square metre self-catering property features one bedroom, one bathroom, sleeps five guests, and includes a private garden, free parking, and a fully equipped kitchen with appliances such as a dishwasher and microwave.
Helter Skelter Matlock - Chesterfield
9.6 97 reviews

Helter Skelter Matlock

house, Matlock
Helter Skelter Matlock is a 3-bedroom house in Matlock, just 13.5 kilometres from Chatsworth House and 32 kilometres from Buxton Opera House. It offers a peaceful and private setting with excellent user, location and cleanliness ratings.
This 500 square metre property sleeps up to 6 guests and is ideal for families. Enjoy the convenience of a fully equipped kitchen, a terrace with mountain views, a garden 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.

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.5 64 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Barrow Hill
This Barrow Hill cottage, a former grocery store, is centrally located, a short walk from the Chesterfield Canal, Cuckoo Way, and the Trans-Pennine Trail, and a short drive (approx. 5km) from Chesterfield town centre and its attractions, including the Crooked Spire church and Queens Park.
The 130 square metre self-catering property sleeps six across three bedrooms, boasting a cosy sitting room with gas fire, a large garden ideal for children, and a fully equipped kitchen including a fridge, microwave, and dishwasher; nearby amenities include a children's playground and excellent access to walking and cycling trails.
Meersbrook Luxury Duplex Apartment - Chesterfield
8.9 138 reviews

Meersbrook Luxury Duplex Apartment

apartment, Sheffield
This luxury duplex apartment is located in Meersbrook, Sheffield, just 8 kilometres from the Utilita Arena Sheffield and 35 kilometres from the Eco-Power Stadium.
The 56 square metre apartment boasts a private entrance, soundproofing, a fully equipped kitchen, a terrace, a garden, and free Wi-Fi, making it a comfortable and convenient base for exploring Sheffield.
Ippleton House - Great Mix Of Town And Country - Chesterfield
9.4 100 reviews

Ippleton House - Great Mix Of Town And Country

apartment
Ippleton House is located on the edge of the Peak District, just 5km from the historic market town of Chesterfield. It has consistently received excellent ratings for cleanliness, location and user experience.
This 3-bedroom home can comfortably accommodate up to 6 guests, and features a private garden, a fully equipped kitchen with a dishwasher, and free parking. Guests can enjoy exploring the Peak District's hiking trails, picturesque villages, and scenic landscapes, or relax in the comfort of the house.
Heart Of The City-flexi Cancellations-central Hub - Chesterfield
9.3 318 reviews

Heart Of The City-flexi Cancellations-central Hub

house, Sheffield
This Sheffield property is conveniently located just 4.2 miles from FlyDSA Arena and 14 miles from Chatsworth House, making it a great base for exploring the city and surrounding areas. The house has consistently received excellent ratings for cleanliness, location, and overall user experience.
The home provides ample space for families or groups of up to 8 guests, with 4 bedrooms and a comfortable living area. Guests can enjoy a fully equipped kitchen, modern amenities like a flat-screen TV and free Wi-Fi, and a relaxing patio with views of the city.

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.

Mill Farm Cottages - Cherry Tree - Chesterfield
No reviews

Mill Farm Cottages - Cherry Tree

apartment
Stunning Barn With Hot Tub On A Secluded Farm - Chesterfield
9.0 2 reviews

Stunning Barn With Hot Tub On A Secluded Farm

house, Eckington
Commuters Getaway Chesterfield - Chesterfield
10 2 reviews

Commuters Getaway Chesterfield

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

Chatsworth Terrace - Chesterfield Centre And Peak District

house, Chesterfield

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.

Spacious 3 Bed House Nr Chesterfield & Mansfield - Chesterfield
No reviews

Spacious 3 Bed House Nr Chesterfield & Mansfield

house, Ault Hucknall

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.

Brampton Terrace: Long Stays, Chesterfield Town - Chesterfield
No reviews

Brampton Terrace: Long Stays, Chesterfield Town

apartment
Barlow Country Club - Mill Farm Cottages - Chesterfield
8.9 404 reviews

Barlow Country Club - Mill Farm Cottages

house, Dronfield
Riber View Barn - Chesterfield
No reviews

Riber View Barn

house, 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
The Loft - Chesterfield
9.0 105 reviews

The Loft

house, Dronfield
Alton Hall Cottage - Chesterfield
10 1 review

Alton Hall Cottage

house, Ashover
215 M² House ∙ 7 Bedrooms ∙ 20 Guests - Chesterfield
9.5 11 reviews

215 M² House ∙ 7 Bedrooms ∙ 20 Guests

house

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.

Spa Home With Hottub And Sauna - Chesterfield
No reviews

Spa Home With Hottub And Sauna

house, Chesterfield
Cottage ∙ 5 Bedrooms ∙ 10 Guests - Chesterfield
No reviews

Cottage ∙ 5 Bedrooms ∙ 10 Guests

cottage, Bolsover
7 Bed In Matlock Oc-89448 - Chesterfield
10 1 review

7 Bed In Matlock Oc-89448

house, Matlock Bank
Riber Hall - Chesterfield
9.6 113 reviews

Riber Hall

house, Matlock Bank
©2026 cozycozy.com