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

Bright - 2 Bedroomed House In Derbyshire - Chesterfield
9.8 113 reviews

Bright - 2 Bedroomed House In Derbyshire

house, Derbyshire
This two-bedroom apartment is located in Chesterfield, just a short walk from the town centre and a 32km drive to Chatsworth House, a renowned stately home. With excellent ratings for location, cleanliness, and user experience, this property offers a comfortable and convenient base for exploring Derbyshire.
The apartment features a private enclosed garden, perfect for relaxing, and is equipped with a modern kitchen including a fridge, freezer, microwave oven, and dishwasher. Guests can enjoy free Wi-Fi and parking, and the apartment is within walking distance of a Lidl supermarket for easy access to groceries.
Oakdale - Our Quest Retreat - Chesterfield
9.7 322 reviews

Oakdale - Our Quest Retreat

apartment
This charming cottage is located at the edge of Hardwick Wood, just 3.2km from Chesterfield and its amenities, offering a peaceful retreat close to the Peak District National Park. It boasts excellent ratings for location, cleanliness and user experience.
The cottage has two bedrooms, sleeping up to four guests, and comes equipped with a fully fitted kitchen, a garden and private parking. Enjoy the peace and quiet of the surrounding woodland, or explore the nearby attractions including Chatsworth House, just a short drive away.
Bramley Vale Home 3 Bed 5 Persons - Chesterfield
No reviews

Bramley Vale Home 3 Bed 5 Persons

apartment, Ault Hucknall
Bramley Vale Home is a recently renovated three-bedroom, two-bathroom apartment situated in a peaceful residential district of Ault Hucknall, offering convenient access to local amenities and the natural beauty of the Derbyshire countryside. This family-friendly accommodation spans 185 square meters and accommodates up to nine guests, featuring a fully equipped kitchen, complimentary WiFi, a private garden, and on-site parking, making it ideal for exploring historical sites and scenic routes.
Peak Edge Home | Fast Wi-fi, Workspaces, 65" Tv! - Chesterfield
9.8 10 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.

Best Chesterfield vacation rentals with parking

Gs Maisons Hideaway - Chesterfield
9.2 5 reviews

Gs Maisons Hideaway

house, Sheffield
GS Maisons Hideaway is a detached property located in Sheffield, 5.8 kilometres from the Utilita Arena Sheffield and 22.5 kilometres from Chatsworth House.
This family-friendly accommodation offers two bedrooms, one bathroom, a fully equipped kitchen with a dishwasher, free Wi-Fi, on-site parking, and a garden, with recreational activities such as billiards and table tennis available.
The Loft At The George - Chesterfield
9.0 41 reviews

The Loft At The George

house, Chesterfield
The Loft at The George is a family-friendly house in Chesterfield, conveniently located 21km from Chatsworth House and 31km from Clumber Park, offering easy access to Derbyshire's attractions.
This 145 square metre property boasts four bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, private parking, and accommodates families or groups, with nearby opportunities for cycling.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.9 36 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Handley
This Handley holiday home, a converted 19th-century Methodist chapel, overlooks Ogston Reservoir in Derbyshire and is a short drive from Bakewell, Matlock, and Ashbourne.
The two-bedroom dwelling, sleeping four, boasts an open-plan living area with an electric wood-burning stove, a country-style kitchen with dishwasher, and a family bathroom; enjoy reservoir views from Velux windows and explore nearby Peak District attractions.
Spacious 3 Bed House Nr Chesterfield & Mansfield - Chesterfield
No reviews

Spacious 3 Bed House Nr Chesterfield & Mansfield

house, Ault Hucknall
This three-bedroom cottage in Ault Hucknall is conveniently located near Chesterfield and Mansfield, with Clumber Park 22.5 kilometres away, Sherwood Forest 25.7 kilometres away, and Chatsworth House 27.3 kilometres away.
This spacious 112 square meter property accommodates up to eight guests and features a fully equipped kitchen with a dishwasher, a private garden, and free WiFi.

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

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.
Park House Studio - Chesterfield
8.9 192 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.
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.
Spa Home With Hottub And Sauna - Chesterfield
No reviews

Spa Home With Hottub And Sauna

house, Chesterfield
House rental listing. This accommodation is located in Chesterfield.
Services and facilities include free parking, a barbecue and a terrace. This house is very convenient for families.

Best Chesterfield vacation rentals with air conditioning

Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre - Chesterfield
9.2 22 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.
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.
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.
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.
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