Holiday Rentals in Chesterfield

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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

Woodview Lodge - Chesterfield
9.9 84 reviews

Woodview Lodge

house, Barlow
Woodview Lodge is a 4-star holiday home located in Barlow, just 42km from Sherwood Forest and 48km from Nottingham Castle, offering easy access to these popular attractions. The lodge has excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The lodge features a private entrance and a spacious layout, accommodating up to 4 guests. The property offers a range of amenities, including a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a tennis court, and free parking, making it ideal for families or groups seeking a relaxing and enjoyable retreat.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Barlow
This Barlow Country Park lodge is located in Barlow, South Yorkshire, on the edge of the Peak District National Park and close to the South Yorkshire border, offering 50 acres of pastures and woodland with 8 fishing lakes nearby.
This pet-friendly, family-friendly two-bedroom bungalow accommodates four guests, featuring an open-plan living space, a private garden, parking for two cars, and complimentary Wi-Fi, serving as a base for exploring the Peak District National Park.
Florries House Is On The Edge Of The Peak District - Chesterfield
9.9 152 reviews

Florries House Is On The Edge Of The Peak District

apartment
This Derbyshire apartment is situated near the picturesque Derbyshire Dales, just a short drive from attractions like Chatsworth House, Bakewell, and Matlock Bath. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The self-catering apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a modern kitchen equipped with a fridge, freezer, and microwave, as well as private parking, internet access, and is within walking distance of local shops, pubs, and takeaways.
Ippleton House - Great Mix Of Town And Country - Chesterfield
9.4 99 reviews

Ippleton House - Great Mix Of Town And Country

apartment
Ippleton House is located on the edge of the Peak District, just 5km from the historic market town of Chesterfield. It has consistently received excellent ratings for cleanliness, location and user experience.
This 3-bedroom home can comfortably accommodate up to 6 guests, and features a private garden, a fully equipped kitchen with a dishwasher, and free parking. Guests can enjoy exploring the Peak District's hiking trails, picturesque villages, and scenic landscapes, or relax in the comfort of the house.

Best Chesterfield holiday rentals with parking

Middlecroft - Chesterfield
8.6 141 reviews

Middlecroft

apartment, Chesterfield
This one-bedroom apartment is located in Chesterfield, just 12 miles from FlyDSA Arena and 16 miles from Chatsworth House, offering easy access to attractions while providing a peaceful setting away from the city. The apartment is highly rated, with excellent cleanliness and very good location and user ratings.
The self-catering apartment can comfortably accommodate up to 4 guests and features a fully equipped kitchen, flat-screen TV, free Wi-Fi, and private parking. Guests can enjoy the convenience of independent check-in and check-out, as well as the added benefit of being in a non-smoking accommodation.
Welcoming 3bdr Home Nr Royal Hospital Chesterfield - Chesterfield
No reviews

Welcoming 3bdr Home Nr Royal Hospital Chesterfield

house, Chesterfield
This three-bedroom detached house in Chesterfield provides convenient access to Chatsworth House (19 kilometres), Clumber Park (27 kilometres), and Utilita Arena Sheffield (26 kilometres).
This property offers accommodation for up to five guests with a garden, private parking, a fully equipped kitchen, and a fireplace, covering a floor area of 7 square meters.
Stunning Central Apartment With Free Parking - Chesterfield
9.3 238 reviews

Stunning Central Apartment With Free Parking

apartment, Sheffield
This centrally located Sheffield flat is just 4.2 miles from FlyDSA Arena and within easy reach of attractions like Chatsworth House and Clumber Park, making it a great base for exploring the city. The property has received excellent ratings for its cleanliness, location and overall user experience.
This two-bedroom apartment is ideal for families or groups of friends. Guests can enjoy free parking, Wi-Fi, a modern kitchen with a fridge, freezer, microwave, and a washing machine, along with comfortable bedding and towels.
Bolsover Castle View - Chesterfield
8.4 94 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.

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

Spacious 4br Retreat For 8 With Parking - Chesterfield
No reviews

Spacious 4br Retreat For 8 With Parking

house, Unstone
This spacious Unstone house, a 16-kilometre drive from the FlyDSA Arena and a 23-kilometre drive from Chatsworth House, offers convenient access to local attractions.
The 158-square-metre property boasts four bedrooms, three bathrooms, sleeps up to eight guests, and includes free Wi-Fi, private parking, a garden, and a terrace.
Relaxed Family Cottage In Matlock, Ideal Peak District Base, 4 Guests - Chesterfield
No reviews

Relaxed Family Cottage In Matlock, Ideal Peak District Base, 4 Guests

house, Matlock
This Matlock cottage serves as an excellent base for exploring the Peak District, located 7.2 kilometres from Chatsworth House and 20 kilometres from Buxton Opera House.
This two-bedroom property accommodates up to 4 guests, offering 150 square meters of living space, a fully equipped kitchen with a dishwasher and oven, free WiFi, free private parking, and a private patio with barbecue facilities.
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.
Springwood Barn No2 Merlyn - Chesterfield
9.8 8 reviews

Springwood Barn No2 Merlyn

house, Sheffield
Springwood Barn No2 Merlyn, near Sheffield, offers a self-catering property 15.1km from Chatsworth House and 16.1km from the FlyDSA Arena.
This two-bedroom house, boasting 61 square metres of floor space, sleeps seven guests and includes a fully equipped kitchen with dishwasher, private terrace, garden, parking, and free Wi-Fi.

Best Chesterfield holiday rentals with air conditioning

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.
Lv8 Chesterfield - Chesterfield
10 3 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.
Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre - Chesterfield
9.2 24 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.
The Little Trout Cottage - Chesterfield
9.1 22 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.
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