Compare Vacation Rentals & Airbnb in Chesterfield

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Chesterfield vacation rentals
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134 Rentals and Airbnb in Chesterfield

Best family friendly Chesterfield vacation rentals

Among the 134 accommodations in Chesterfield, here are the 4 best family friendly rentals

3 Bedroom Accommodation In Inkersall, Near Chesterfield - Chesterfield
Chesterfield
03/09 – 06/09
$303/nighttotal: $909 (3 )

3 Bedroom Accommodation In Inkersall, Near Chesterfield

3 2
cottage , Inkersall, near Chesterfield
This Inkersall riverside cottage, near Chesterfield, is 1.8km from Poolsbrook Country Park, 5km from the Barrow Hill Roundhouse Railway Centre, and under 5km from the Pomegranate Theatre.
Sleeping five guests, this three-bedroom holiday home boasts a fully equipped kitchen, private patio, garden, parking, and Wi-Fi; enjoy nearby waterside activities or explore Chesterfield's attractions.
Unit 1 Bright & Classy 1-bdr Flat, Fast Wi-fi, Free Parking, Intimate Location - Chesterfield
9.8 5 reviews
Chesterfield
21/08 – 23/08
$275/nighttotal: $550 (2 )

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

1 2
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.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.6 52 reviews
Chesterfield
08/08 – 09/08
$678/nightfor 1 night

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
cottage
This charming two-bedroom cottage is situated on Matlock Moor, just 2 kilometres north of the spa town of Matlock and a short walk from the Matlock Golf Club, offering a peaceful rural setting. It has consistently received excellent reviews from guests.
The cottage provides 105 square metres of space, comfortably accommodating up to four guests. It features a well-equipped kitchen, a cosy living area, a private garden, and parking, making it ideal for families or groups of friends looking for a relaxing getaway.
Heart Of The City-flexi Cancellations-central Hub - Chesterfield
9.3 313 reviews
Chesterfield
26/06 – 28/06
$517/nighttotal: $1034 (2 )

Heart Of The City-flexi Cancellations-central Hub

3 4
house , Sheffield
This Sheffield property is conveniently located just 4.2 miles from FlyDSA Arena and 14 miles from Chatsworth House, making it a great base for exploring the city and surrounding areas. The house has consistently received excellent ratings for cleanliness, location, and overall user experience.
The home provides ample space for families or groups of up to 8 guests, with 4 bedrooms and a comfortable living area. Guests can enjoy a fully equipped kitchen, modern amenities like a flat-screen TV and free Wi-Fi, and a relaxing patio with views of the city.

Best Chesterfield vacation rentals with parking

The Long Hall 2 Bed Ground Floor Annexed Apartment - Chesterfield
9.9 342 reviews
Chesterfield
26/09 – 27/09
$362/nightfor 1 night

The Long Hall 2 Bed Ground Floor Annexed Apartment

2 2
apartment , Chesterfield
This two-bedroom apartment is situated in a peaceful residential area in Chesterfield, just a short walk from the town centre and its attractions. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The self-catering property has a spacious living area with a sofa bed, accommodating up to six guests. Amenities include a fully equipped kitchen, private courtyard, shared garden, parking for three cars, high-speed Wi-Fi, and a Virgin Media TV package.
Refurbished Plush Property Great Transport Links - Chesterfield
9.4 284 reviews
Chesterfield
26/06 – 28/06
$509/nighttotal: $1018 (2 )

Refurbished Plush Property Great Transport Links

3 4
house , Sheffield
This property is located in Sheffield, just 6 kilometres from the FlyDSA Arena, offering easy access to major attractions like Chatsworth House (24 kilometres) and Cusworth Hall (39 kilometres). The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house has 3 bedrooms and 1 bathroom, comfortably accommodating up to 10 guests. It features a fully equipped kitchen, a private garden with a patio, free parking, and free Wi-Fi, making it an ideal choice for families or groups visiting Sheffield.
Modern, City Centre, Studio Apartment With Free Wifi, Gym Access, Netflix - West One - Chesterfield
9.4 426 reviews
Chesterfield
07/07 – 08/07
$182/nightfor 1 night

Modern, City Centre, Studio Apartment With Free Wifi, Gym Access, Netflix - West One

1 1
studio , Sheffield
This modern studio apartment is located in Sheffield city centre, just 6.4 kilometres from FlyDSA Arena and 25.7 kilometres from Chatsworth House. The studio has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers.
The self-catering apartment features a well-equipped kitchen, a comfortable living area, and a modern bathroom, comfortably accommodating up to three guests. Enjoy complimentary Wi-Fi, Netflix, and access to a fitness room, perfect for staying connected and active during your stay.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
Chesterfield
25/06 – 16/07
$387/nighttotal: $8127 (21 )

Cottage ∙ 1 Bedroom ∙ 2 Guests

1 2
cottage
Oak Tree Retreat is a one-bedroom, one-bathroom cottage for two located in the Peak District countryside, offering immediate access to natural beauty. This open-plan living pod features a comfortable double bed, a Smart TV, a kitchen, complimentary Wi-Fi, and a sustainable Cinderella toilet, with private parking and a garden sitting-out area.

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.

Destinations nearby

Best Chesterfield vacation rentals with a balcony

The Golden House, Spacious Family Home, Parking, Garden - Chesterfield
Chesterfield
08/08 – 09/08
$877/nightfor 1 night

The Golden House, Spacious Family Home, Parking, Garden

1 2
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.
Gate Cottage - Chesterfield
9.6 361 reviews
Chesterfield
07/07 – 08/07
$251/nightfor 1 night

Gate Cottage

2 1
house , Matlock
Gate Cottage is conveniently located in the centre of Matlock, within easy walking distance of shops, restaurants and country walks. This charming house has received excellent ratings for its location, cleanliness and overall user experience.
The cottage features two bedrooms, one bathroom, and a floor area of 12 square metres. Guests can enjoy a range of amenities including a fully equipped kitchen with a fridge, microwave oven and dishwasher, a terrace or balcony, a garden, a tennis court, parking and complimentary internet access.
Open Haven Collective With Man Cave And Parking 10ppl - Chesterfield
10 2 reviews
Chesterfield
02/07 – 06/07
$375/nighttotal: $1500 (4 )

Open Haven Collective With Man Cave And Parking 10ppl

1 1
house , Handsworth
This detached house is located in Handsworth, 4.5 kilometres from the Utilita Arena Sheffield and 27 kilometres from Chatsworth House.
This property offers 79 square metres of living space with 3 bedrooms and 1 bathroom, accommodating up to 10 guests and featuring a 'Man Cave', a garden, and free private parking.
The Coach House Central Location Fantastic Views - Chesterfield
9.4 115 reviews
Chesterfield
03/09 – 06/09
$389/nighttotal: $1167 (3 )

The Coach House Central Location Fantastic Views

2 2
house , Matlock
The Coach House is located in Matlock, just 14 kilometres from Chatsworth House and 35 kilometres from Buxton Opera House, offering a peaceful retreat in the heart of the Peak District. Guests consistently rate the house highly for its cleanliness, location, and overall experience.
The 84 square metre property has two bedrooms, two bathrooms, and can comfortably accommodate up to seven guests. It features a fully equipped kitchen, a terrace, a garden, free parking, and modern amenities like a flat-screen TV with streaming services, making it ideal for families and groups looking to explore the scenic Peak District.

Best Chesterfield vacation rentals with air conditioning

Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 8 reviews
Chesterfield
02/07 – 06/07
$588/nighttotal: $2352 (4 )

Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise

3 1
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.
Number 26 Van Dyk Village - Chesterfield
9.8 14 reviews
Chesterfield
26/06 – 28/06
$491/nighttotal: $982 (2 )

Number 26 Van Dyk Village

3 4
house , Chesterfield
This three-bedroom house, situated in Van Dyk Village, Chesterfield, is conveniently located 19km from Sherwood Forest, 26km from the FlyDSA Arena, and 32km from Clumber Park.
The 42 square metre property offers free Wi-Fi, private parking, a patio, and sleeps up to nine guests, boasting a fully equipped kitchen, living room and a peaceful garden setting.
Spacious 4 Bed Home For Families & Contractors. - Chesterfield
10 1 review
Chesterfield
21/08 – 23/08
$376/nighttotal: $752 (2 )

Spacious 4 Bed Home For Families & Contractors.

4 2
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.
Riber Hall - Chesterfield
9.6 105 reviews
Chesterfield
08/08 – 09/08
$5260/nightfor 1 night

Riber Hall

6 2
house , Matlock Bank
Riber Hall is located in Matlock Bank, Derbyshire, just 12 miles from Chatsworth House and 23 miles from Buxton Opera House, making it an ideal base for exploring the Peak District. The property has received excellent ratings for user experience, location, and cleanliness.
This six-bedroom, six-bathroom home offers 30 square metres of space, perfect for large families or groups. Guests can enjoy a private patio with an outdoor fireplace, a terrace with garden views, a hot tub, a fully equipped kitchen, and a tranquil garden.
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