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

Haddon Cottage - Chesterfield
8.8 8 reviews

Haddon Cottage

apartment
This apartment is located just a short distance from the charming town of Matlock, close to Darwin Lake and within easy reach of Bakewell, Ashbourne and Chesterfield, all within 30km. It has received excellent ratings for its location, cleanliness and overall experience.
The apartment is perfect for families, with three bedrooms and three bathrooms, accommodating up to six guests. The large kitchen comes equipped with a fridge, microwave, dishwasher and washer/dryer, while the living area offers a comfortable space to relax, perfect for enjoying a family meal or a quiet evening in.
Rent My Spa Home With Pool Table Hottub And Sauna - Chesterfield
9.9 169 reviews

Rent My Spa Home With Pool Table Hottub And Sauna

house, Chesterfield
This seven-bedroom house is situated in a peaceful rural location, approximately 25 km from FlyDSA Arena and 20 km from Chatsworth House. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The house spans 215 square metres and offers a range of amenities including a jacuzzi, sauna, fitness centre, and a spacious garden with a patio, hot tub, barbecue, and pool table.
Peveril Cottage - Chesterfield
9.5 17 reviews

Peveril Cottage

apartment
Peveril Cottage is a charming lakeside retreat just 5km from Matlock, offering a peaceful escape in the heart of the Peak District. This cottage has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The cottage has two bedrooms, two bathrooms, and can accommodate up to four guests. Amenities include a well-equipped kitchen, a garden, parking, and internet access, making it perfect for families looking to explore the surrounding area.
Derbyshire Holiday Cottages - Chesterfield
9.5 146 reviews

Derbyshire Holiday Cottages

house, Holmesfield
Derbyshire Holiday Cottages is a 2-bedroom house located in Holmesfield, a village in Derbyshire, just 14.5 kilometres from Chatsworth House and 17.7 kilometres from Utilita Arena Sheffield.
This family-friendly accommodation offers a peaceful garden, free parking, a fully equipped kitchen, free Wi-Fi, a flat-screen TV, and a terrace, with a maximum guest capacity of 7 people.

Best Chesterfield vacation rentals with parking

Southdown House Doe Lea By Smart Corporate Stays - Chesterfield
9.5 2 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.
Cheerful 2- Bedroomed Home In Chesterfield. - Chesterfield
9.8 182 reviews

Cheerful 2- Bedroomed Home In Chesterfield.

house
This charming townhouse is located on the edge of the Peak District, just a 3km walk from Chesterfield's Market Town and a 32km drive from the main attractions of the Peak District. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The home offers 2 bedrooms and 1 bathroom, comfortably accommodating up to 4 guests. Amenities include a fully equipped kitchen with a fridge and dishwasher, a private garden, and parking, making it a perfect choice for families or groups looking for a relaxing and convenient stay.
Tissington Cottage- Darwin Lake Holiday Village - Chesterfield
9.0 77 reviews

Tissington Cottage- Darwin Lake Holiday Village

house, Matlock
Tissington Cottage, a 2-bedroom house in Matlock, Derbyshire, is situated 12km from Chatsworth House and offers easy access to fishing and cycling opportunities.
This 60 square metre property sleeps up to 8 guests and boasts 2 bathrooms, free Wi-Fi, a private garden with BBQ, and free on-site parking.
Smithy Cottage - Chesterfield
9.5 14 reviews

Smithy Cottage

house, Dronfield
Smithy Cottage, a two-bedroom house in Dronfield, Derbyshire, enjoys a peaceful location 14.8 km from Chatsworth House, 22.5 km from Sheffield, and 35.4 km from Buxton.
This 105 square metre property sleeps seven, boasting a fully equipped kitchen with dishwasher, garden, parking, free Wi-Fi, and a fireplace; pets are welcome.

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

Park House Studio - Chesterfield
8.9 203 reviews

Park House Studio

studio, Matlock
Park House Studio, a self-contained apartment in Matlock, Derbyshire, is conveniently located 14.5km from Chatsworth House and 35.4km from Buxton Opera House.
This 25 square metre studio sleeps two, features a fully equipped kitchen with dishwasher, private terrace, garden, parking, and free Wi-Fi, offering easy access to Matlock's hiking trails.
Meersbrook Duplex Apartment - Chesterfield
9.0 138 reviews

Meersbrook 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.
Barlow Country Club - Mill Farm Cottages - Chesterfield
9.0 408 reviews

Barlow Country Club - Mill Farm Cottages

house, Dronfield
Barlow Country Club - Mill Farm Cottages is located in Dronfield, just a short drive from Chatsworth House and FlyDSA Arena, offering a peaceful retreat in the countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottages are family-friendly and pet-friendly, featuring a garden, terrace, and a restaurant on-site. Guests can enjoy free Wi-Fi, a fully equipped kitchen, and a tennis court, making it ideal for a relaxing and enjoyable stay.
Little Manor - Chesterfield
8.3 57 reviews

Little Manor

house, Chesterfield
Little Manor is a sustainable holiday home located in Chesterfield, just 22 kilometres from Chatsworth House and 24 kilometres from FlyDSA Arena, offering a peaceful escape in a quiet neighbourhood. The property has received very good ratings for its cleanliness, location and overall experience.
The two-bedroom home comfortably sleeps four guests and features a well-equipped kitchen with a fridge, microwave and toaster. Guests can enjoy the outdoor space with a patio and garden, free parking and a terrace with views of the quiet street.

Best Chesterfield vacation rentals with air conditioning

The Coach House At Stretton House - Chesterfield
No reviews

The Coach House At Stretton House

house, Stretton
The Coach House is located on Highstairs Lane in Stretton, 46 kilometres from East Midlands Airport.
This private accommodation offers two bedrooms and two bathrooms for up to eleven guests, featuring air conditioning, a kitchenette, complimentary WiFi, and electric vehicle charging, with private parking available.
Lv8 Chesterfield - Chesterfield
10 1 review

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.
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.
Cool "Beautiful " 1757 Stone Cottage In Hot Summer - Chesterfield
9.9 39 reviews

Cool "Beautiful " 1757 Stone Cottage In Hot Summer

apartment
This charming stone cottage is located just a short walk from Dove Dale, a beautiful valley in the Peak District, and is within easy reach of popular attractions like Chatsworth House and Haddon Hall, both within 10km. The cottage has consistently received excellent ratings for location, cleanliness, and overall experience.
The property sleeps four guests comfortably in two bedrooms, including a double bed and a sofa bed in the lounge. The cottage boasts a fully equipped kitchen with a Stanley cast iron cooker, a washing machine, a tumble dryer, a dishwasher, and a modern wet room with a power shower. Guests can enjoy the garden with a pergola, BBQ, and patio area, and explore the nearby Peak District with its stunning nature trails and charming pubs.
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