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

2 Bedroom Accommodation In Old Brampton, Near Chesterfield - Chesterfield
10 13 reviews

2 Bedroom Accommodation In Old Brampton, Near Chesterfield

cottage, Old Brampton, near Chesterfield
This 2-bedroom holiday cottage in Old Brampton, near Chesterfield, is located in a rural setting approximately 3 minutes from moors and escarpments, offering direct access to countryside walks and nature trails, and is a short drive from Chatsworth House, Haddon Hall, and Hardwick Hall.
This family-friendly and pet-friendly property accommodates up to 4 guests with Wi-Fi, a garden, patio, and private parking for 2 cars, making it ideal for exploring local pubs (0.25 km away) and historic market towns.
Little Hive-uk39430 - Chesterfield
9.8 31 reviews

Little Hive-uk39430

house, Dronfield
Little Hive-UK39430, a self-catering holiday home in Dronfield, is conveniently located 13.5 km from the Utilita Arena Sheffield and 17.7 km from Chatsworth House, offering easy access to other attractions within a 40 km radius.
This one-bedroom property sleeps a couple or small group, boasting a fully equipped kitchen with a dishwasher, free Wi-Fi, private parking, and a private entrance; guests can enjoy a peaceful getaway close to Sheffield and the Peak District.
Spacious Sheffield Group Home With Fireplace, Piano And Garden - Chesterfield
8.0 1 review

Spacious Sheffield Group Home With Fireplace, Piano And Garden

apartment, Nether Edge
This Nether Edge accommodation is situated in Sandford Grove, a short walk from Abbeydale Road's independent shops and restaurants, and approximately 10 kilometres by car from Sheffield city centre and the Peak District National Park.
This family-friendly apartment accommodates up to 11 guests, offering three bathrooms, a kitchen with a fridge, a private garden with a BBQ, and free WiFi, making it ideal for groups exploring Sheffield and the surrounding Peak District.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
No reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
Carr House Farm, a farmhouse cottage on a working farm near Wingerworth, Derbyshire, offers woodland walks directly from the property and is conveniently located for day trips to Bakewell, Chatsworth, and Chesterfield. This family-friendly property accommodates up to six guests across three bedrooms, features a kitchen with a fridge, microwave oven, and dishwasher, and welcomes pets, with stables available on request.

Best Chesterfield vacation rentals with parking

Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District - Chesterfield
9.4 13 reviews

Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District

house, Brimington
Tapton View, a modern holiday home in Brimington, Derbyshire, offers convenient access to Chesterfield town centre, Chesterfield railway station, and the Peak District National Park.
This two-bedroom property boasts 50 square metres of living space, including a living room with flat-screen TV, fully equipped kitchen with dining area, bathroom with bath and washing machine, and sleeps up to 11 guests, with free Wi-Fi and parking.
Bolsover Castle View - Chesterfield
8.4 96 reviews

Bolsover Castle View

apartment, Bolsover
Bolsover Castle View, a self-catering apartment in Bolsover, Derbyshire, is conveniently located within 21km of Clumber Park, 24km from Sherwood Forest, and 29km from Chatsworth House.
This 74 square metre property sleeps seven guests in two bedrooms and one bathroom, offering free Wi-Fi, a fully equipped kitchen, garden, parking, and amenities including a washing machine, flat-screen TV, and fireplace.
Tawny Cottage - Chesterfield
10 4 reviews

Tawny Cottage

apartment
This 4-bedroom stone-built house in Chesterfield offers secluded private drive parking and is situated 12 kilometers from the Peak District National Park, with convenient access to Chatsworth House and Haddon Hall.
This residence provides accommodation for up to 8 guests, featuring a fully equipped kitchen, a separate dining room, a comfortable living room, and a dedicated office space, alongside off-road parking.
The Corner House - Chesterfield
9.7 3 reviews

The Corner House

house, Chesterfield
The Corner House, a recently renovated holiday home in Chesterfield, is situated 18km from the Utilita Arena Sheffield and 23km from Chatsworth House.
This two-bedroom property boasts 120 square metres of living space, including a living room, fully equipped kitchen with dishwasher, a bathroom with walk-in shower and bath, private balcony, parking and sleeps up to seven guests.

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

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.
Peak Retreat - Chesterfield
9.1 10 reviews

Peak Retreat

house, Chesterfield
This recently renovated 65 square meter holiday home is located in a peaceful district of Chesterfield, offering convenient access to local amenities and attractions within a short distance.
This pet-friendly accommodation features two bedrooms, one bathroom, and a fully equipped kitchen, with Wi-Fi and a private terrace, accommodating up to 11 guests.
The Olde Coach House - Chesterfield
9.4 12 reviews

The Olde Coach House

house, Chesterfield
The Olde Coach House is a tranquil retreat located 19 kilometres from Chatsworth House, offering a peaceful escape from the hustle and bustle of Chesterfield town. The property has received excellent ratings for its cleanliness, location, and overall user experience.
This 3-bedroom, 2-bathroom property spans 120 square metres and can comfortably accommodate up to 11 guests. Enjoy a range of on-site amenities including a fitness centre, tennis court, and a Jacuzzi, as well as a well-equipped kitchen, a spacious garden, and a terrace for outdoor dining.
Springwood Barn No1 Forest - Chesterfield
10 9 reviews

Springwood Barn No1 Forest

house, Holmesfield
Springwood Barn No1, a self-catering property in Holmesfield, is situated 15.1 km from Chatsworth House and 16.1 km from the FlyDSA Arena.
This one-bedroom house offers 63 square metres of space, sleeping up to 7 guests and boasting two bathrooms, a private garden with terrace, free parking, and Wi-Fi.

Best Chesterfield vacation rentals with air conditioning

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.
Thesignature# Groups #Contractors #Parking #Wi-fi* - Chesterfield
No reviews

Thesignature# Groups #Contractors #Parking #Wi-fi*

apartment
This executive suite in Chesterfield is located near the city centre, offering a 5-minute walk to supermarkets and the hospital, and is 3.06 kilometres from the train station.
This spacious apartment features four bedrooms, two and a half bathrooms, and accommodates up to six guests with versatile sleeping arrangements, including air conditioning and on-site parking via a garage and driveway, ideal for contractors and groups seeking long stays with weekly and monthly booking discounts.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 7 reviews

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

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.
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.
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