Vacation Rentals in Chesterfield

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Chesterfield holiday rentals
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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

Cottage ∙ 5 Bedrooms ∙ 12 Guests - Chesterfield
9.8 21 reviews
Chesterfield
04/07 – 05/07
A$2390/nightfor 1 night

Cottage ∙ 5 Bedrooms ∙ 12 Guests

5 2
cottage , Tansley
Oakwood House, a five-bedroom holiday home in Tansley, Derbyshire, is 2.7km from Matlock and a short drive from Chatsworth House and the Peak District National Park.
This self-catering property sleeps 12, boasts a fully equipped kitchen with dishwasher, five en-suite bedrooms (two ground floor), a spacious dining room, enclosed garden, and Smart TV, offering ample space for families or groups.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 16 reviews
Chesterfield
04/07 – 05/07
A$1222/nightfor 1 night

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
cottage
Moor Farm Cottage, a Derbyshire self-catering property, is situated in the Peak District National Park, 3.2km from Ashover and 8km from Matlock, offering easy access to Chatsworth House and other historical sites.
This 105 square metre holiday home features two bedrooms sleeping four, a spacious open-plan living area, a private hot tub, on-site gym, and is close to walking and cycling trails.
Unit 1 Comfortable 1-br Flat, Free Wi-fi, Free Parking, Intimate Location - Chesterfield
9.8 5 reviews
Chesterfield
08/08 – 09/08
A$318/nightfor 1 night

Unit 1 Comfortable 1-br Flat, Free 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.
The Loft At The George - Chesterfield
9.4 37 reviews
Chesterfield
07/07 – 08/07
A$1100/nightfor 1 night

The Loft At The George

4 1
house , Chesterfield
The Loft at The George is a family-friendly house in Chesterfield, conveniently located 21km from Chatsworth House and 31km from Clumber Park, offering easy access to Derbyshire's attractions.
This 145 square metre property boasts four bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, private parking, and accommodates families or groups, with nearby opportunities for cycling.

Best Chesterfield holiday rentals with parking

Bolsover Castle View - Chesterfield
8.8 83 reviews
Chesterfield
21/08 – 23/08
A$181/nighttotal: A$362 (2 )

Bolsover Castle View

2 2
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.
Beautiful Grade Ii Listed Gatehouse In Great Location - Chesterfield
9.6 199 reviews
Chesterfield
21/08 – 23/08
A$266/nighttotal: A$532 (2 )

Beautiful Grade Ii Listed Gatehouse In Great Location

1 2
house , Sheffield
This Grade II Listed Gatehouse is conveniently located in Sheffield, just a short distance from the FlyDSA Arena and a longer drive from Chatsworth House. The property is highly rated for its location, cleanliness and overall experience.
The charming house offers one bedroom and one bathroom, with a floor area of 44 square metres, comfortably accommodating two guests. Enjoy the peaceful garden views, relax in the well-equipped kitchen with a fridge, freezer and dishwasher, and make the most of the free parking and Wi-Fi.
Manor House - Chesterfield
9.6 103 reviews
Chesterfield
08/08 – 09/08
A$3923/nightfor 1 night

Manor House

5 2
house , Chesterfield
The Manor House is located in Chesterfield, a short drive from Chatsworth House (21 km), FlyDSA Arena (26 km), Clumber Park (27 km), and Sherwood Forest (34 km), offering easy access to popular attractions. The house has received excellent user ratings for its cleanliness, location, and overall experience.
The property is a spacious five-bedroom home with a floor area of 160 square metres, accommodating up to 10 guests. The Manor House includes a fully equipped kitchen, a swimming pool, a Jacuzzi, a terrace, a garden, and a fitness centre, providing everything needed for a relaxing and enjoyable stay.
Fairfield Snug - Ashover Village Super King-twin - Chesterfield
9.9 7 reviews
Chesterfield
21/08 – 23/08
A$165/nighttotal: A$330 (2 )

Fairfield Snug - Ashover Village Super King-twin

1 2
apartment , Ashover
This recently renovated Ashover apartment is situated 17.7 kilometres from Chatsworth House and 32.2 kilometres from Utilita Arena Sheffield.
This 22 square metre flat offers accommodation for up to three guests, with a terrace, on-site parking, complimentary WiFi, and an on-site coffee shop for convenience.

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

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.
Wisteria Corner - Tranquil Home, Friends & Family - Chesterfield
Chesterfield
26/06 – 28/06
A$619/nighttotal: A$1238 (2 )

Wisteria Corner - Tranquil Home, Friends & Family

1 4
house , Newbold
This Newbold detached house, Wisteria Corner, is located in a familiar district and is 16 kilometres from Chatsworth House and 22 kilometres from Utilita Arena Sheffield.
This spacious 186 square metre property accommodates 15 guests with one bedroom, three bathrooms, a fully equipped kitchen, a terrace, and free private parking, offering a tranquil home environment with Wifi and a fireplace.
3-bedroom Home In Matlock, Heart Of Peak District - Chesterfield
9.0 1 review
Chesterfield
03/09 – 06/09
A$351/nighttotal: A$1053 (3 )

3-bedroom Home In Matlock, Heart Of Peak District

3 2
house , Matlock
This detached house in Matlock is located within the Peak District, 11.7 kilometres from Chatsworth House and 32.2 kilometres from Buxton Opera House.
This 250 square meter property accommodates up to nine guests across three bedrooms and features a fully equipped kitchen, two bathrooms, a private patio, a garden, and free private parking.
The Carriage - Chesterfield
10 1 review
Chesterfield
02/07 – 06/07
A$161/nighttotal: A$644 (4 )

The Carriage

1 1
apartment , Matlock
This Matlock flat is located 7.2 kilometres from Chatsworth House and offers convenient access to Sheffield and Nottingham.
This one-bedroom flat, covering 12 square metres, accommodates up to three guests and features a kitchen, terrace, and complimentary Wi-Fi, with free private parking available.

Best Chesterfield holiday rentals with air conditioning

Riber Hall - Chesterfield
9.6 105 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.
The Stables East Lodge Country House - Chesterfield
8.1 17 reviews
Chesterfield
02/07 – 06/07
A$629/nighttotal: A$2516 (4 )

The Stables East Lodge Country House

3 1
house , Great Rowsley
This Peak District country retreat in Great Rowsley offers a peaceful escape, situated 6.1km from Chatsworth House and 26km from Buxton Opera House.
The 362 square metre property sleeps up to 13 guests, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, air conditioning, private parking, Wi-Fi, and a terrace with garden views.
Hip Hideaway In The Trendiest Part Of Town - Chesterfield
10 3 reviews
Chesterfield
07/07 – 08/07
A$267/nightfor 1 night

Hip Hideaway In The Trendiest Part Of Town

2 1
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.
The Urban Residence - Sheffield 6br Group-family Stay - Sleeps 12 - Chesterfield
Chesterfield
03/09 – 06/09
A$879/nighttotal: A$2637 (3 )

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

6 2
apartment , 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.
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