Compare Vacation Rentals & Airbnb in Chesterfield

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Chesterfield vacation rentals
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193 Rentals and Airbnb in Chesterfield

Best family friendly Chesterfield vacation rentals

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

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

The Golden House, Spacious Family Home, Parking, Garden

house, Ecclesall
The Golden House is a detached residence located in the Ecclesall district, offering proximity to Utilita Arena Sheffield (10.3 kilometres) and Chatsworth House (19.3 kilometres).
This property, ideal for families, provides 138 square meters of living space, accommodates up to 9 guests, and features a garden, terrace, free WiFi, and private parking.
Spacious Loft Apartment With Far Reaching Views Of The Countryside - Chesterfield
8.7 11 reviews

Spacious Loft Apartment With Far Reaching Views Of The Countryside

apartment, Matlock
This spacious loft apartment in Matlock offers far-reaching countryside views and is situated 11 kilometres from Chatsworth House and 30 kilometres from Buxton Opera House.
This pet-friendly family accommodation sleeps up to seven guests, features a fully equipped kitchen with a dishwasher, complimentary WiFi, and free on-site parking, with a walk-in shower and bath in the bathroom.
Habberjam Farm - Swimming Pool, Hot Tub, Sauna, Games Room - Chesterfield
9.8 26 reviews

Habberjam Farm - Swimming Pool, Hot Tub, Sauna, Games Room

house, Sheffield
Habberjam Farm, a spacious five-bedroom house near the Peak District National Park, is situated 12.7km from Utilita Arena Sheffield and 25.7km from Chatsworth House.
This 166 square metre property sleeps up to 19 guests and boasts a fully equipped kitchen, two bathrooms, a games room, a fire pit, private parking, and a garden with outdoor play equipment.
Unit 1 Bright & Classy 1-bdr Flat, Fast Wi-fi, Free Parking, Intimate Location - Chesterfield
9.8 5 reviews

Unit 1 Bright & Classy 1-bdr Flat, Fast Wi-fi, Free Parking, Intimate Location

apartment, Sheffield
This Sheffield apartment, conveniently located 6.4km from the FlyDSA Arena and within a reasonable driving distance of Chatsworth House, offers guests easy access to major attractions.
The 30-square-metre self-catering flat features one bedroom, one bathroom, sleeps three, and includes free private parking, Wi-Fi, a balcony, and a garden.

Best Chesterfield vacation rentals with parking

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.
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.
Commuters Getaway Chesterfield - Chesterfield
10 2 reviews

Commuters Getaway Chesterfield

house, Chesterfield
This apartment is situated in Chesterfield, just a 15-minute walk from Queen's Park, Mecca Bingo, and Chesterfield Market, and within 2km of Chesterfield Museum & Art Gallery and Pomegranate Theatre, making it ideal for exploring the town's attractions. The property is located in a quiet area, offering a peaceful retreat from the town centre.
The apartment features a kitchen equipped with a fridge and microwave oven, as well as a garden and a jacuzzi for relaxation. Guests can also enjoy free parking and Wi-Fi, ensuring a comfortable and convenient stay.
Spa Home With Hottub And Sauna - Chesterfield
No reviews

Spa Home With Hottub And Sauna

house, Chesterfield
Vacation house to rent. You will be based in Chesterfield.
Facilities and services: an iron, a dish washer and free parking. Take advantage of the jacuzzi in this house.

Frequently Asked Questions about vacation rentals in Chesterfield

  • What should a first-time visitor not miss in Chesterfield?

    You've got to see the Crooked Spire, it's a real icon of Chesterfield. The town's museum is also brilliant, you'll learn all about the history of the area. And if you're into gardens, the Queen's Park is a must-see.
  • What are the best Airbnb and vacation rentals in Chesterfield?

    3 Bedroom House Near Woods - Edge Of Peak District, The Long Hall 2 Bed Ground Floor Annexed Apartment and The Barn At Woodland View are the most popular Airbnb and vacation rentals in Chesterfield among travelers.

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

    The town centre is great for being near the shops and restaurants, but if you want a bit more peace and quiet, try the areas around Queen's Park or Walton.
  • What are the most popular Airbnbs in Chesterfield?

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

    The Chesterfield Museum and Art Gallery is great for kids, they have lots of interactive exhibits. The Chesterfield Canal is also brilliant for a family walk or bike ride, and you can even hire a boat.
  • What are the best vacation rentals with a pool in Chesterfield?

    Manor House, Family Fun Party House Pool - Bar - Sauna - Cinema and Tawny Owl Barn are the best vacation rentals with a pool in Chesterfield.

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

    If you want to avoid the crowds, book your rental outside of school holidays. The summer months are always busy, so booking in advance is essential.
  • What are the best rentals for families and kids in Chesterfield?

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

    The Chesterfield Food and Drink Festival is always a hit, and there's also the Chesterfield Beer Festival in the autumn. For something a bit different, check out the Chatsworth Country Fair, it's just a short drive away.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?

    The best vacation rentals or Airbnb with a jacuzzi in Chesterfield are Spapartyhome With Hottub Sauna Bbq & Pool Table, Manor House and Hot Tub House Close To Woodland And Peak District.

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

    A walk along the Chesterfield Canal is free and offers beautiful views. You can also visit the Queen's Park, which is a great place to relax and enjoy the outdoors.
  • What are the best restaurants with local dishes in Chesterfield?

    The Old Vicarage is a popular choice for traditional pub grub, and you can't go wrong with The Little Chef for a classic British breakfast. For something a bit fancier, try The Tap, they do a great Sunday roast.
  • What are the best walking or cycling routes in Chesterfield?

    The Chesterfield Canal towpath is a lovely walk, and there are plenty of cycling routes through the Peak District National Park nearby. The Chesterfield to Staveley cycle path is a good option.
  • Are there pet-friendly attractions in Chesterfield?

    The Queen's Park is dog-friendly, and many of the pubs and restaurants in the town centre welcome dogs too. The Chesterfield Canal towpath is also great for walking your dog.
  • What are the benefits of choosing a vacation rental in Chesterfield?

    Vacation rentals offer more space and privacy than a hotel, and you can often find rentals with unique features, like a garden or a hot tub. They are also often a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Chesterfield?

    The Proact Stadium is home to Chesterfield FC, and the town has a number of other sports facilities, including a bowling alley, a leisure centre, and a golf course.

Popular destinations

Best Chesterfield vacation rentals with a balcony

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.
Southdown House Doe Lea By Smart Corporate Stays - Chesterfield
9.3 3 reviews

Southdown House Doe Lea By Smart Corporate Stays

house, Ault Hucknall
Southdown House, a four-bedroom property in Ault Hucknall, Nottinghamshire, offers convenient access to attractions such as Clumber Park (24km), Chatsworth House (29km), Sherwood Forest (30km), Nottingham Castle (35km), and the Utilita Arena Sheffield (35km).
This 132 square metre self-catering house boasts a spacious layout including a living room, fully equipped kitchen, two bathrooms, free Wi-Fi, private parking, and a terrace; accommodating up to 39 guests.
Yew Tree Cottage, Pet Friendly, Luxury Holiday Cottage In Matlock - Chesterfield
No reviews

Yew Tree Cottage, Pet Friendly, Luxury Holiday Cottage In Matlock

cottage, Matlock
This pet-friendly cottage in Matlock is a 0.6km walk from Matlock Parks Country Park and Hall Leys Park, and 0.8km from Matlock railway station, offering easy access to the Peak District National Park.
The 105 square metre property sleeps four, boasting two bedrooms, one bathroom, and a fully equipped kitchen including a dishwasher, microwave, and fridge, plus on-site parking.
Brampton Terrace Chesterfield Centre & Peaks - Chesterfield
No reviews

Brampton Terrace Chesterfield Centre & Peaks

apartment, Chesterfield
This Chesterfield flat is located 16 kilometres from Chatsworth House and 24 kilometres from Utilita Arena Sheffield, with East Midlands Airport 56 kilometres away.
This 70 square metre apartment offers one bedroom, one bathroom, and accommodates up to eleven guests, featuring a fully equipped kitchen, a terrace with city views, and free WiFi.

Best Chesterfield vacation rentals with air conditioning

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.
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.
Lv8 Chesterfield - Chesterfield
10 2 reviews

Lv8 Chesterfield

apartment
This luxury apartment is located centrally in Chesterfield, Derbyshire, a short 500-meter walk from local shops, restaurants, and the historic Crooked Spire.
This one-bedroom, one-bathroom designer flat accommodates two guests and features a unique dungeon-themed bedroom, air conditioning, and Wi-Fi for a distinctive getaway.
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