Vacation Rentals in Chesterfield

134 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Chesterfield holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

134 Holiday rentals and Airbnb in Chesterfield

Best family friendly Chesterfield holiday rentals

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

The Rumblings 1 - Chesterfield
8.7 27 reviews
Chesterfield
21/08 – 23/08
A$359/nighttotal: A$718 (2 )

The Rumblings 1

2 2
house , Barlow
The Rumblings 1, a Barlow holiday home, offers peaceful accommodation within easy reach of Chatsworth House (11km), Utilita Arena Sheffield (21km), Buxton Opera House (32km), and Sherwood Forest (50km).
This 105 square metre property features two bedrooms, one bathroom, a fully equipped kitchen with fridge and microwave, free Wi-Fi, private parking, and accommodates up to four guests, plus one well-behaved dog; nearby cycling is also available.
The Pig Sty - Chesterfield
9.8 2 reviews
Chesterfield
21/08 – 23/08
A$966/nighttotal: A$1932 (2 )

The Pig Sty

2 2
house , Barlow
The Pig Sty is a pet-friendly house in Barlow, Derbyshire, situated 13.5 km from Chatsworth House and within easy reach of attractions including the FlyDSA Arena and Buxton Opera House.
This two-bedroom, two-bathroom property offers guests free Wi-Fi, private parking, a swimming pool, a hot tub, and a fully equipped kitchen with a dishwasher; enjoy a relaxing stay with access to a garden and fireplace.
Spacious 4br, Parking, Near Centre, Accommodates 7 - Chesterfield
9.1 271 reviews
Chesterfield
26/06 – 28/06
A$295/nighttotal: A$590 (2 )

Spacious 4br, Parking, Near Centre, Accommodates 7

4 4
house , Sheffield
Olive Grove House is located in Sheffield, just 6.6 kilometres from the FlyDSA Arena, offering easy access to the city's main attractions, while being in a peaceful setting. The property has received excellent ratings for its cleanliness, location and user experience.
This 4-bedroom home can accommodate up to 8 guests and has a fully equipped kitchen, a terrace, a garden, and parking. Enjoy the city views from the patio, relax in the garden, and stay connected with free Wi-Fi.
Cottage ∙ 4 Bedrooms ∙ 5 Guests - Chesterfield
Chesterfield
18/10 – 26/10
A$563/nighttotal: A$4504 (8 )

Cottage ∙ 4 Bedrooms ∙ 5 Guests

4 5
cottage
This accessible bungalow, Havendale, is located in historic Chesterfield, Derbyshire, just 1.4 kilometers from the medieval market town centre and its famous 'Crooked Spire', with the Peak District National Park, Chatsworth House, and Haddon Hall within easy driving distance.
This architecturally designed, single-storey property accommodates up to five guests in four bedrooms, featuring an open-plan living space with an accessible kitchen, a woodburning stove, and wide bifold doors leading to an enclosed south-facing garden with a barbecue, whilst pets and families are welcome.

Best Chesterfield holiday rentals with parking

Blissful Barrys - Chesterfield
8.8 22 reviews
Chesterfield
26/06 – 28/06
A$257/nighttotal: A$514 (2 )

Blissful Barrys

3 4
house , Chesterfield
Blissful Barrys is a 3-bedroom house located in Chesterfield, just 22.5 kilometres from Utilita Arena Sheffield and 24 kilometres from Chatsworth House. The property has received very good user and location ratings, and an excellent cleanliness rating.
The house offers 12 square metres of space and can accommodate up to 9 guests. Guests can enjoy a private garden and terrace, free parking, a fully equipped kitchen, a washing machine, and free Wi-Fi.
Payler 4 Bedroom House Stylish With 7 Beds Parking Near M1 - Chesterfield
9.4 7 reviews
Chesterfield
27/06 – 04/07
A$436/nighttotal: A$3052 (7 )

Payler 4 Bedroom House Stylish With 7 Beds Parking Near M1

4 8
house , Sheffield
This charming house is situated just 5 kilometres from FlyDSA Arena and within easy reach of Chatsworth House (27 kilometres) and Eco-Power Stadium (31 kilometres), offering a convenient base for exploring Sheffield and the surrounding area. The property is ideal for families or groups, with 4 bedrooms, a living room, and a fully equipped kitchen, offering 120 square metres of space for up to 10 guests.
Enjoy a peaceful stay with a private entrance and soundproofing, and relax in the garden with patio views. The house has free Wi-Fi, a large parking space, and comfortable amenities including towels and bed linen.
1 Bedroom Accommodation In Dronfield - Chesterfield
10 1 review
Chesterfield
21/08 – 23/08
A$331/nighttotal: A$662 (2 )

1 Bedroom Accommodation In Dronfield

1 2
cottage , Dronfield
This one-bedroom apartment is situated in Dronfield, a town on the edge of the Peak District National Park, just 10km from Sheffield and 15km from Chesterfield, offering a peaceful escape from the city. The apartment is part of a converted barn on a 40-acre gated property with over 30 horses, perfect for a relaxing getaway.
The apartment has an open-plan living space ideal for two guests, with a well-equipped kitchen and comfortable sofas. Enjoy free WiFi, a dishwasher, a coffee machine, private parking for two cars, and easy access to local shops, restaurants, and attractions like the Peak District, Chesterfield, and the charming village of Hathersage.
Unit 4 Well-filled 1-br Flat, Near Bramall Lane, High Speed Wifi, Secure Parking - Chesterfield
10 1 review
Chesterfield
04/07 – 05/07
A$304/nightfor 1 night

Unit 4 Well-filled 1-br Flat, Near Bramall Lane, High Speed Wifi, Secure Parking

1 2
apartment , Sheffield
This modern Sheffield apartment is conveniently located near Bramall Lane, approximately 6.4km from the FlyDSA Arena, making it ideal for football fans and concert-goers.
The 30-square-metre flat features one bedroom, one bathroom, a fully equipped kitchen, private parking, and a balcony, comfortably accommodating up to three guests and offering free Wi-Fi.

Frequently asked questions about holiday rentals in Chesterfield

  • Which neighborhood in Chesterfield should you consider for a vacation rental?

    If you want to be right in the centre of things, the town centre is ideal. But if you want something a bit quieter, maybe look at the areas around Queen's Park or Walton.
  • What are the best Airbnb and holiday rentals in Chesterfield?

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

    The Chesterfield Museum & Art Gallery is great for kids, they've got interactive exhibits. The Chesterfield Canal is also a good option, you can take a boat trip or go for a walk along the towpath.
  • What are the most popular Airbnbs in Chesterfield?

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

    You'll get the best deals if you book outside of peak season, which is generally July and August. But if you want to be here for the Chesterfield Food and Drink Festival, you'll need to book well in advance.
  • What are the best holiday rentals with a pool in Chesterfield?

    Manor House, Family Fun Party House Pool - Bar - Sauna - Cinema and Tawny Owl Barn are the best holiday rentals with a pool in Chesterfield.

  • What events or festivals should visitors check out in and around Chesterfield?

    The Chesterfield Food and Drink Festival is a big one, held in the town centre. There's also the Chesterfield Mayfair, a traditional fair with rides and stalls.
  • What are the best rentals for families and kids in Chesterfield?

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

    A walk along the Chesterfield Canal is always free, and the views are lovely. The Chesterfield Museum & Art Gallery has free entry on certain days, so check their website.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?

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

  • What are the best restaurants with local dishes in Chesterfield?

    The Crooked Spire pub is a local favourite, and they serve traditional pub grub. For something a bit fancier, try The Little Chef, they do a great Sunday roast.
  • Are there pet-friendly attractions in Chesterfield?

    The Chesterfield Canal towpath is dog-friendly, and many pubs and cafes welcome dogs too. The Chesterfield Museum & Art Gallery doesn't allow dogs inside, though.
  • What are the benefits of choosing a vacation rental in Chesterfield?

    You'll have more space and privacy than a hotel, and you can often get a better price. Plus, you'll be able to cook your own meals, which can save you money.
  • What are the top sports attractions and facilities in Chesterfield?

    The Proact Stadium is home to Chesterfield FC, so if you're a football fan, you'll want to check out a game. For other sports, there's the Queen's Park Sports Centre, which has a swimming pool and gym.

Destinations nearby

Best Chesterfield holiday rentals with a balcony

Luxury Apartment - Great Location - Chesterfield
9.4 70 reviews
Chesterfield
07/07 – 08/07
A$262/nightfor 1 night

Luxury Apartment - Great Location

1 1
apartment , Ecclesall
This Ecclesall apartment, conveniently located 9.6km from the Utilita Arena Sheffield and 22.5km from Chatsworth House, offers easy access to local attractions.
The 85 square metre flat features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen with dishwasher, free Wi-Fi, private parking, and a terrace.
West One Panorama, City View, Secure Free Parking, 4pp - Chesterfield
10 3 reviews
Chesterfield
07/07 – 08/07
A$405/nightfor 1 night

West One Panorama, City View, Secure Free Parking, 4pp

1 1
apartment , Sheffield
This Sheffield city centre apartment, located 0.5km from the city centre and 6.6km from the FlyDSA Arena, offers easy access to shops, restaurants, and cultural attractions.
The 55 square metre flat features one bedroom, one bathroom, free parking, a balcony, and a fully equipped kitchen including a fridge, microwave, and dishwasher, comfortably sleeping four guests.
Harriers Grove House - Chesterfield
9.5 11 reviews
Chesterfield
27/06 – 04/07
A$741/nighttotal: A$5187 (7 )

Harriers Grove House

4 8
house , Skegby
Harriers Grove House is located in Skegby, just 21 kilometres from Sherwood Forest and 22 kilometres from Clumber Park, offering a peaceful retreat in a quiet town. The property has received excellent ratings for its cleanliness, location and overall user experience.
This 4-bedroom home provides a spacious living room with a fireplace and a shared lounge area. The kitchen is equipped with a fridge and microwave oven, and the house also offers a terrace with garden views, free parking, and Wi-Fi.
Cosy Flat With Sunny Terrace - Chesterfield
8.5 2 reviews
Chesterfield
21/08 – 23/08
A$189/nighttotal: A$378 (2 )

Cosy Flat With Sunny Terrace

1 2
apartment , Ecclesall
This Ecclesall flat is located 8.9 kilometres from Utilita Arena Sheffield and 20.9 kilometres from Chatsworth House.
This 12 square metre, one-bedroom flat accommodates up to three guests and features a kitchen with a fridge and microwave oven, a private terrace with garden views, and on-site parking, with free Wi-Fi available throughout.

Best Chesterfield holiday rentals with air conditioning

Spacious 4 Bed Home For Families & Contractors. - Chesterfield
10 1 review
Chesterfield
21/08 – 23/08
A$383/nighttotal: A$766 (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.
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise - Chesterfield
9.0 8 reviews
Chesterfield
21/08 – 23/08
A$2132/nighttotal: A$4264 (2 )

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

3 2
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.
Riber Hall - Chesterfield
9.6 107 reviews
Chesterfield
08/08 – 09/08
A$5352/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.
Number 26 Van Dyk Village - Chesterfield
9.8 14 reviews
Chesterfield
26/06 – 28/06
A$500/nighttotal: A$1000 (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.
©2026 cozycozy.com