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.

Spire Haven - Chesterfield
9.9 24 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.
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 - Modern Chesterfield Town Centre Apartments - Chesterfield
9.4 189 reviews

The Corner House - Modern Chesterfield Town Centre Apartments

apartment, Chesterfield
The Corner House apartments are situated in Chesterfield town centre, just a short drive from Chatsworth House and FlyDSA Arena. These apartments have consistently received excellent ratings for location, cleanliness, and overall user experience.
The modern apartments offer a comfortable and convenient stay. You'll find a fully equipped kitchen, free Wi-Fi, private parking, and a contemporary design with flat-screen TVs and private bathrooms.
Town Centre Modern Apartment - Chesterfield
9.7 129 reviews

Town Centre Modern Apartment

apartment
This modern flat is just a short walk from Chesterfield town centre, making it perfect for exploring both the historic market town and the nearby Peak District National Park. The apartment has excellent user, location, and cleanliness ratings, guaranteeing a comfortable and enjoyable stay.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to three guests. Amenities include a fully equipped kitchen, parking, and high-speed internet, ensuring a convenient and enjoyable stay.

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.
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.
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.
Thesignature# Groups #Contractors #Parking #Wi-fi* - Chesterfield
No reviews

Thesignature# Groups #Contractors #Parking #Wi-fi*

apartment
This executive suite in Chesterfield is located near the city centre, offering a 5-minute walk to supermarkets and the hospital, and is 3.06 kilometres from the train station.
This spacious apartment features four bedrooms, two and a half bathrooms, and accommodates up to six guests with versatile sleeping arrangements, including air conditioning and on-site parking via a garage and driveway, ideal for contractors and groups seeking long stays with weekly and monthly booking discounts.

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.

Morden House Close To City Centre & The Peaks - Chesterfield
9.3 48 reviews

Morden House Close To City Centre & The Peaks

house, Chesterfield
This modern house is located in Chesterfield, just 24 km from Nottingham and 9.3 km from Sheffield, offering easy access to both cities and the scenic Peak District. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The property features 3 bedrooms, comfortably accommodating up to 6 guests, and spans 139 square metres. The house is equipped with a range of amenities, including a fully equipped kitchen, a terrace, a garden, a spa, parking, and concierge services.
Ringinglow Cottage - Chesterfield
9.2 49 reviews

Ringinglow Cottage

house, Sheffield
Toy Cottage Sheffield is located on a quiet street in Sheffield, just 8.5 kilometres from Sheffield Train Station and 22.5 kilometres from Haddon Hall. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottage is a one-bedroom property with one bathroom, covering 23 square metres and accommodating up to two guests. It offers a fully equipped kitchen with a dishwasher, oven, and microwave, a terrace with quiet street views, and free private parking, making it perfect for a comfortable and convenient stay in Sheffield.
Kspace @ The Point - Chesterfield
9.1 1015 reviews

Kspace @ The Point

apartment, Sheffield
This apartment is conveniently located in Sheffield city centre, just a short walk from City Hall, KSpace, and the Crucible Theatre, offering easy access to the city's cultural attractions and vibrant nightlife. The apartment has received excellent ratings for cleanliness, location, and overall experience, making it a popular choice for travellers.
The apartment features a comfortable living room, a fully equipped kitchen with a fridge, microwave, and dishwasher, and a private bathroom, accommodating up to two guests. Guests can enjoy a terrace or balcony, parking, and access to the internet, as well as a washing machine/dryer and a Smart flat-screen TV with Netflix.
Dogs Welcome Peaks Retreat Views 3br Sleep 5 - Chesterfield
9.1 7 reviews

Dogs Welcome Peaks Retreat Views 3br Sleep 5

house, Matlock
This detached house in Matlock is located within the Peak District, 11.7 kilometres from Chatsworth House and 32.2 kilometres from Buxton Opera House.
This 250 square meter property accommodates up to nine guests across three bedrooms and features a fully equipped kitchen, two bathrooms, a private patio, a garden, and free private parking.

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.

Helter Skelter Matlock - Chesterfield
9.7 98 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.
Boythorpe House - Chesterfield
8.5 8 reviews

Boythorpe House

apartment
Boythorpe House is located in Chesterfield, 18km from Chatsworth House, 25km from FlyDSA Arena, and 31km from Clumber Park, offering a peaceful retreat away from the hustle and bustle of the city centre. The property has received excellent user ratings and is considered very good in terms of cleanliness and location.
The house has a shared lounge and kitchen, and a garden with views, covering 115 square metres. It offers free Wi-Fi, parking, and is suitable for families and pets, with a shared kitchen, allowing guests to prepare their own meals.
Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District - Chesterfield
9.4 13 reviews

Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District

house, Brimington
Tapton View, a modern holiday home in Brimington, Derbyshire, offers convenient access to Chesterfield town centre, Chesterfield railway station, and the Peak District National Park.
This two-bedroom property boasts 50 square metres of living space, including a living room with flat-screen TV, fully equipped kitchen with dining area, bathroom with bath and washing machine, and sleeps up to 11 guests, with free Wi-Fi and parking.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 47 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This semi-detached holiday home is located just a short distance from Matlock, a charming town in the heart of the Peak District National Park, offering breathtaking views of the Derbyshire Dales. The cottage is situated on the edge of the National Park, making it an ideal base for exploring the stunning scenery and outdoor activities on offer.
The cottage has two bedrooms and can comfortably accommodate up to four guests. It offers a range of amenities, including a fully equipped kitchen, a spacious garden, a hot tub, and a conservatory, making it perfect for relaxing and enjoying the beautiful surroundings.

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.

Ritas Retreat - Chesterfield
10 209 reviews

Ritas Retreat

gîte
Ellie's Place - Chesterfield
10 29 reviews

Ellie's Place

apartment
Yew Tree Cottage - Chesterfield
9.2 2 reviews

Yew Tree Cottage

house, Old Brampton
3 Bed In Ashover Oc-w30175 - Chesterfield
9.6 5 reviews

3 Bed In Ashover Oc-w30175

house, Ashover

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.

Chesterfield Long Term Stay, Bills Included - Chesterfield
10 1 review

Chesterfield Long Term Stay, Bills Included

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.

Hygge House - Chesterfield
9.5 164 reviews

Hygge House

house, Matlock
Harris House - Chesterfield
9.0 3 reviews

Harris House

house, Staveley
Spindle Cottage, Peak District - Chesterfield
10 9 reviews

Spindle Cottage, Peak District

apartment
Springwood Barn No1 Forest - Chesterfield
10 9 reviews

Springwood Barn No1 Forest

house, Holmesfield

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.

Central Blue Haven Retreat Free Parking 8ppl! - Chesterfield
9.0 19 reviews

Central Blue Haven Retreat Free Parking 8ppl!

apartment, Victoria
215 M² House ∙ 7 Bedrooms ∙ 20 Guests - Chesterfield
9.5 11 reviews

215 M² House ∙ 7 Bedrooms ∙ 20 Guests

house
Central Sheffield Stadium House 15ppl Free Parking - Chesterfield
9.5 4 reviews

Central Sheffield Stadium House 15ppl Free Parking

house, Sheffield
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 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.

Farmhouse ∙ 5 Bedrooms ∙ 10 Guests - Chesterfield
No reviews

Farmhouse ∙ 5 Bedrooms ∙ 10 Guests

farm, Marsh Lane
Spa Home With Hottub And Sauna - Chesterfield
No reviews

Spa Home With Hottub And Sauna

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

Wigley Farm House Cottage

apartment
Cherry Tree Cottage - Chesterfield
9.4 7 reviews

Cherry Tree Cottage

house, Chesterfield
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