Holiday Rentals in Chesterfield

193 available vacation rental offers

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Chesterfield holiday rentals
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Chesterfield holiday rentals: compare the best deals

Best family friendly Chesterfield holiday rentals

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

2 Snape Hill - Chesterfield
9.5 43 reviews

2 Snape Hill

house, Dronfield
2 Snape Hill is a holiday home in Dronfield, just 14 km from FlyDSA Arena, 19 km from Chatsworth House, and 36 km from Clumber Park, making it a great base for exploring the Peak District. Guests consistently rate the property excellent for its location, cleanliness, and overall experience.
This three-bedroom property offers 130 square metres of space, comfortably accommodating up to six guests. The house has a fully equipped kitchen with a fridge, microwave, and dishwasher, a garden, parking, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
The Urban Residence - Sheffield 6br Group-family Stay - Sleeps 12 - Chesterfield
No reviews

The Urban Residence - Sheffield 6br Group-family Stay - Sleeps 12

house, Victoria
The Urban Residence is a spacious six-bedroom flat located in the Sheffield district of Victoria, offering convenient access to local attractions.
This family-friendly apartment provides accommodation for up to 12 guests, featuring a private terrace, free WiFi, complimentary private parking, and a car rental service on-site.
Spire Haven - Chesterfield
9.9 23 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.
Oakdale - Our Quest Retreat - Chesterfield
9.7 316 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.

Best Chesterfield holiday rentals with parking

Farley Cottage - Chesterfield
9.3 16 reviews

Farley Cottage

apartment
Farley Cottage is located on the edge of Darwin Lake Holiday Village, close to the ancient woodland treeline, and within easy reach of Matlock, Ashbourne, Chesterfield and Bakewell.
This three-bedroom, three-bathroom self-catering cottage sleeps six guests and is perfect for families or groups visiting the Peak District, with its proximity to attractions such as Alton Towers and Gulliver's Kingdom.
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.
Modern 3 Bed Home, Chesterfield - Chesterfield
9.8 12 reviews

Modern 3 Bed Home, Chesterfield

apartment
This modern three-bedroom flat is located in the heart of Chesterfield, just a short walk from the town centre and its shops, restaurants, and historical attractions. It has received excellent user ratings for its location, cleanliness, and overall experience.
The flat comfortably accommodates up to five guests and features a spacious living area, a fully equipped kitchen with a washing machine and dishwasher, a private enclosed rear garden with a decking area, and off-street parking. Guests can enjoy the modern interior, the ensuite bathroom in one of the double bedrooms, and the proximity to Derbyshire attractions like Chatsworth House and the Peak District National Park, all within a 30-kilometre drive.
Spacious 5br House In Staveley Wi-fi Sleeps 10 - Chesterfield
9.7 3 reviews

Spacious 5br House In Staveley Wi-fi Sleeps 10

house, Staveley
This five-bedroom detached house in Staveley is located 19 kilometres from Utilita Arena Sheffield and 24 kilometres from Chatsworth House.
This property offers accommodation for up to 10 guests across its 89 square metres, featuring a fully equipped kitchen, three bathrooms, a private garden, and free Wi-Fi, with parking available.

Frequently asked questions about holiday rentals in Chesterfield

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

    You definitely want to see the Crooked Spire, it's Chesterfield's most famous landmark. A trip to the Chesterfield Museum & Art Gallery is a must too, it's a great way to learn about the history of the town. And for a bit of green space, the Queen's Park is a lovely spot to relax.
  • 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 a good bet if you want to be close to the action. If you're looking for something a bit quieter, try the area around Queen's Park, it's lovely and green.
  • What are the most popular Airbnbs in Chesterfield?

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

    Chesterfield's a great place for families. You've got the Chesterfield Canal, which you can explore by boat, the Chesterfield Museum & Art Gallery has lots of interactive exhibits for kids, and the Queen's Park has a playground and lots of open space to run around in.
  • What are the best vacation rentals with a pool in Chesterfield?

    Manor House, Family Fun Party House Pool - Bar - Sauna - Cinema and The Pig Sty are the best vacation rentals with a pool in Chesterfield.

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

    The best time to book a vacation rental in Chesterfield is usually during the shoulder seasons, like spring and autumn, when the weather's nice and the prices are a bit lower. You might want to book a bit earlier if you're planning to visit during the summer, especially if you're coming for a festival or event.
  • 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 a big one, it's held in the town centre and has lots of stalls selling local produce. And there's the Chesterfield Beer Festival, which takes place at the Winding Wheel.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?

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

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

    A walk along the Chesterfield Canal is free and a great way to see the town. The Chesterfield Museum & Art Gallery has free entry, and the Queen's Park is a beautiful spot to relax and enjoy the sunshine.
  • What are the best restaurants with local dishes in Chesterfield?

    The Old House is a popular choice, they serve classic British dishes and have a great atmosphere. For something a bit more modern, try The Tap, they do delicious burgers and have a good selection of craft beers.
  • What are the best walking or cycling routes in Chesterfield?

    The Chesterfield Canal towpath is a great place for a walk or cycle, it stretches for miles and takes you past some lovely countryside. You can also find some good walking trails in the Queen's Park.
  • Are there pet-friendly attractions in Chesterfield?

    The Queen's Park is a great place to take your dog for a walk, and many pubs in the town centre are dog-friendly.
  • 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 one with a kitchen so you can cook your own meals. They're also a good option if you're travelling with a family or a group of friends.
  • What are the top sports attractions and facilities in Chesterfield?

    The Proact Stadium is home to Chesterfield FC, a popular football club, and there's also a bowling alley and a leisure centre with a swimming pool.

Popular destinations

Best Chesterfield holiday rentals with a balcony

Home From Home | 2-bed Chesterfield Stay - Chesterfield
No reviews

Home From Home | 2-bed Chesterfield Stay

apartment, Brimington
This Brimington flat is situated in Chesterfield, offering convenient access to Chatsworth House (12 kilometers away), Barrow Hill Roundhouse Railway Centre (3 kilometers away), Sheffield (24 kilometers away), and the Peak District National Park.
This two-bedroom residence accommodates up to four guests, featuring a fully equipped kitchen, a modern bathroom with a walk-in shower, complimentary Wi-Fi, and on-site parking, making it ideal for both short and extended stays.
Springwood Cottage - Chesterfield
9.9 266 reviews

Springwood Cottage

apartment, Holmesfield
Springwood Cottage is located in Holmesfield, just 16.1 km from Chatsworth House and 16.1 km from FlyDSA Arena, offering a peaceful escape from the hustle and bustle. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The self-catering apartment spans 48 square meters and comfortably accommodates up to 4 guests. It features a fully equipped kitchen, a terrace, a garden, and free private parking, making it an ideal choice for families or groups of friends exploring the Peak District.
Peak Retreat - Chesterfield
10 1 review

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.
Cosy Matlock Cottage With Valley Views - Chesterfield
No reviews

Cosy Matlock Cottage With Valley Views

apartment, Matlock Bath
This traditional cottage is located in a peaceful, historic area of Matlock, offering a 10-minute walk to Matlock town centre and a 20-minute walk to Matlock Bath, with the Peak District easily accessible.
This 79 square meter, two-bedroom, two-bathroom holiday let accommodates up to four guests and features a private terrace with valley and river views, a log burner, a fully equipped kitchen/diner, and is dog-friendly for up to two well-behaved dogs.

Best Chesterfield holiday rentals with air conditioning

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.
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.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 8 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.
Lv8 Chesterfield - Chesterfield
10 1 review

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.