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

193 Holiday rentals and Airbnb in Chesterfield

Best family friendly Chesterfield holiday rentals

Among the 193 accommodations in Chesterfield, here are the 4 best family friendly rentals

Comfortable 2 Bedroom Apartment - Chesterfield
8.0 3 reviews

Comfortable 2 Bedroom Apartment

apartment, Sheffield
This two-bedroom flat in Sheffield is situated approximately 4.8 kilometres from the Utilita Arena Sheffield and 16 kilometres from Chatsworth House.
This family-friendly apartment accommodates up to five guests and features a fully equipped kitchen, a flat-screen television, and parking.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.3 129 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This first-floor apartment in Matlock, Derbyshire, offers stunning views of Riber Castle and Matlock church, and is a short drive (approximately 10km) from Bakewell and Ashover, the filming location for parts of the Peak Practice TV series.
Knowleston Place cottage sleeps four guests in two bedrooms, features a modern kitchen with a fridge and dishwasher, and provides free parking and Wi-Fi; enjoy its open-plan living area with mullioned windows overlooking Riber Castle.
Peak Edge Home | Fast Wi-fi, Workspaces, 65" Tv! - Chesterfield
9.8 8 reviews

Peak Edge Home | Fast Wi-fi, Workspaces, 65" Tv!

apartment
This 2-bedroom flat offers a prime location on the outskirts of Chesterfield, placing you on the doorstep of the Peak District National Park and within easy reach of Chesterfield town centre, approximately 3.5 kilometers away.
This family-friendly property accommodates up to six guests with a fully equipped kitchen, super-fast Wi-Fi, a 65" TV, and both driveway and free street parking, making it ideal for exploring Derbyshire's natural beauty and local amenities.
Prime Location 2 Bed | Parking Included - Chesterfield
10 5 reviews

Prime Location 2 Bed | Parking Included

apartment
This two-bedroom flat is located in Chesterfield, Derbyshire, a short walk from the town centre and the iconic Crooked Spire, with easy access to the Peak District National Park.
This pet-friendly accommodation offers free on-site parking, internet, a kitchen, and accommodates up to four guests, making it ideal for contractors, families, and weekend getaways.

Best Chesterfield holiday rentals with parking

Chesterfield Royal Hospital And The Peak District - Chesterfield
10 9 reviews

Chesterfield Royal Hospital And The Peak District

apartment
This Calow flat is ideally located 800 meters from Chesterfield Royal Hospital and 5 minutes from the town centre, with Peak District attractions such as Chatsworth House a 30-kilometer drive away.
This well-appointed two-bedroom flat accommodates four guests and offers a log burner, fast WiFi, a Smart TV, a fully equipped kitchen, and a garden with patio, with unique bathroom access via the main bedroom.
Spindle Cottage, Peak District - Chesterfield
10 2 reviews

Spindle Cottage, Peak District

apartment
This 2-bedroom cottage in Holymoorside is located on the edge of the Peak District, offering immediate access to moorland and woodland walks, and is situated 11 kilometres from Chatsworth House.
This property accommodates up to 4 guests and features a log-burning stove, a fully equipped kitchen with a coffee corner, and a private garden, with two pubs and a local shop within 500 metres.
Cosy 2 Bed Home Chesterfield - Chesterfield
9.9 40 reviews

Cosy 2 Bed Home Chesterfield

apartment, Chesterfield
This apartment is located in Chesterfield, just 21 km from Chatsworth House and 22 km from FlyDSA Arena, offering a peaceful setting with garden views. The property has received excellent ratings for cleanliness, location, and overall experience.
The home features two bedrooms, one bathroom, and a floor area of 50 square metres, accommodating up to four guests. Amenities include a kitchen with a fridge, freezer, and microwave, as well as internet access, parking, and a garden.
Chatsworth Terrace: Chesterfield Centre & Peaks - Chesterfield
No reviews

Chatsworth Terrace: Chesterfield Centre & Peaks

apartment, Derbyshire
This two-bedroom flat is located in Chesterfield's S40 postcode, a short 100 meters from Chatsworth Road and serves as an excellent base for exploring the Peak District National Park.
This pet-friendly apartment accommodates up to six guests and offers fast Wi-Fi, a dedicated workspace, a shared garden, and is conveniently situated for accessing local amenities and outdoor pursuits.

Frequently asked questions about holiday rentals in Chesterfield

  • Which neighborhood in Chesterfield should you consider for a vacation rental?

    The town centre is great for exploring, but for a quieter stay, look at properties near Queen's Park. It's a lovely green space, perfect for a relaxing stroll.
  • What are the best Airbnb and holiday rentals in Chesterfield?

  • What are the top family-friendly attractions in Chesterfield?

    The Chesterfield Canal is a great place for a family walk or bike ride. And for a fun day out, the Chesterfield Museum & Art Gallery has plenty to keep kids entertained.
  • What are the most popular Airbnbs in Chesterfield?

  • When is the best time to book a vacation rental in Chesterfield?

    It depends what you're after. If you want to catch the Chesterfield Festival, you'll need to book well in advance. Otherwise, you can usually find good deals outside of peak season.
  • 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.

  • What events or festivals should visitors check out in and around Chesterfield?

    The Chesterfield Festival is a big one, and the Bakewell Show is a good day out for the whole family. If you're here in December, the Christmas Market is a festive treat.
  • What are the best rentals for families and kids in Chesterfield?

  • What are the best budget-friendly activities in Chesterfield?

    The Chesterfield Canal towpath is free to walk or cycle, and the Queen's Park is a great place for a picnic. You can also visit the Chesterfield Museum & Art Gallery for free.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?

    The best vacation 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.

  • Are there pet-friendly attractions in Chesterfield?

    Queen's Park is dog-friendly, and many pubs and restaurants in the town centre welcome well-behaved dogs. You can also walk the Chesterfield Canal towpath with your furry friend.
  • What are the benefits of choosing a vacation rental in Chesterfield?

    You'll have more space and privacy than a hotel, and you can often save money, especially if you're travelling with a family or group. Plus, you'll get a more authentic experience of the town.
  • What are the top sports attractions and facilities in Chesterfield?

    The Proact Stadium is home to Chesterfield FC, and there are several golf courses in the area, including the Chesterfield Golf Club. The Queen's Park has a great playground for kids.

Popular destinations

Best Chesterfield holiday rentals with a balcony

Round House View - Chesterfield
9.6 21 reviews

Round House View

house, Chesterfield
Round House, a Brimington house, is conveniently located 21km from Chatsworth House and the Utilita Arena Sheffield.
This 61 square metre property sleeps nine guests and boasts a fully equipped kitchen, private terrace, garden, parking, and Wi-Fi; a washing machine is also provided.
The Bungalow@barlow, Pet Friendly, With Open Fire In Chesterfield - Chesterfield
10 1 review

The Bungalow@barlow, Pet Friendly, With Open Fire In Chesterfield

cottage, Dronfield
This charming cottage is situated just 3km from Chesterfield and 10km from the Peak District National Park, offering a peaceful retreat on the outskirts of Dronfield. It's consistently rated excellent by guests, making it a popular choice for travellers seeking a comfortable stay.
The cottage sleeps up to five guests in two bedrooms, perfect for families or groups of friends. It's equipped with modern amenities like a dishwasher and washing machine, plus a large garden with a patio and access to an orchard.
Little Fairfield - Chesterfield
9.0 4 reviews

Little Fairfield

apartment, Ashover
This Ashover flat, located at Little Fairfield, is 17.7 kilometres from Chatsworth House and 32.2 kilometres from Utilita Arena Sheffield, with Clumber Park and Sherwood Forest also within a 38.6 kilometre radius.
This compact 18 square metre studio apartment accommodates two guests with one bedroom and one bathroom, offering complimentary high-speed WiFi, a kitchenette, and free on-site parking.
Holiday Haven Oasis Hot Tub Sauna Driveway - Chesterfield
No reviews

Holiday Haven Oasis Hot Tub Sauna Driveway

house, Frecheville
This one-bedroom holiday cottage is located in the Frecheville district, offering a peaceful residential setting with easy access to local amenities and green spaces.
This pet-friendly holiday home provides 73 square meters of living space, featuring a fully equipped kitchen, a hot tub, and a sauna, with parking and WiFi included for up to 19 guests.

Best Chesterfield holiday rentals with air conditioning

Stylish Home From Home - Chesterfield
9.3 20 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.
Affordable 1br Flat By Ankers Short Term Lets Matlock Bath With Exclusive Summer Savings - Chesterfield
9.1 12 reviews

Affordable 1br Flat By Ankers Short Term Lets Matlock Bath With Exclusive Summer Savings

apartment, Matlock Bank
This Matlock Bank apartment is conveniently located 14km from Chatsworth House, 32km from Alton Towers, and 34km from Buxton Opera House, offering easy access to the Peak District National Park.
Sleeping six guests, this self-catering flat boasts a king-size bed, a fully equipped kitchen, free Wi-Fi, air conditioning, parking, and one bathroom.
Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre - Chesterfield
9.2 24 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.
Spacious 4 Bed Home For Families & Contractors. - Chesterfield
10 1 review

Spacious 4 Bed Home For Families & Contractors.

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.
©2026 cozycozy.com