Vacation Rentals in Chesterfield

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Chesterfield holiday rentals
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193 Holiday rentals and Airbnb in Chesterfield

Uncover Top-Tier Family Holiday Rentals in Chesterfield

Book a spacious home base equipped with a full kitchen and open living areas at family holiday rentals in Chesterfield.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Holymoorside
Mill Close Cottage, a delightful holiday home in Holymoorside, Derbyshire, enjoys easy access to the Monsal Trail and is within 20km of Chatsworth House and Bakewell.
This pet-friendly (dogs only) two-bedroom property offers ground-floor accessibility, sleeps four, includes a well-equipped kitchen and utility room, and boasts private parking for two cars.
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.
75 M² House ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

75 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Bolsover
Castle View, a newly renovated Bolsover dwelling, enjoys a convenient location just 8 kilometres from Junction 29a of the M1 motorway.
This 75 square metre property offers two bedrooms, one bathroom, and sleeps four, featuring an open-plan downstairs area, a well-equipped kitchen, and family-friendly amenities including a travel cot and highchair.
3 Bedroom Accommodation In Inkersall, Near Chesterfield - Chesterfield
No reviews

3 Bedroom Accommodation In Inkersall, Near Chesterfield

cottage, Inkersall, near Chesterfield
This Inkersall riverside cottage, near Chesterfield, is 1.8km from Poolsbrook Country Park, 5km from the Barrow Hill Roundhouse Railway Centre, and under 5km from the Pomegranate Theatre.
Sleeping five guests, this three-bedroom holiday home boasts a fully equipped kitchen, private patio, garden, parking, and Wi-Fi; enjoy nearby waterside activities or explore Chesterfield's attractions.

Best Chesterfield holiday rentals with parking

The Corner House - Chesterfield
9.7 24 reviews

The Corner House

apartment
This New Whittington house, situated on the High Street, offers easy access to local amenities and is within walking distance of New Whittington's shops, restaurants, and pubs.
The two-bedroom property features a stylish open-plan kitchen and lounge, a quirky converted cellar room, a private courtyard, high-speed broadband (160MB fibre), and comfortably accommodates four guests.
Garden Cottage - Ashover Village Near Matlock - Chesterfield
9.8 174 reviews

Garden Cottage - Ashover Village Near Matlock

house, Chesterfield
Garden Cottage, a recently renovated self-catering property in Ashover Village, enjoys a convenient location near Matlock and Chesterfield, approximately 18km from Chatsworth House and 35km from the Utilita Arena Sheffield.
This one-bedroom house, boasting 49 square metres of floor space, offers a fully equipped kitchen, private garden, patio, free Wi-Fi, parking, and a tennis court, ideal for a peaceful retreat for two guests.
Edwardian Home Sleeps 6 Chesterfield - Chesterfield
10 3 reviews

Edwardian Home Sleeps 6 Chesterfield

house, Whittington
This Edwardian property in Whittington is located 17.7 kilometres from Chatsworth House and 17.7 kilometres from Utilita Arena Sheffield.
This spacious 120 square metre house offers 3 bedrooms, 2 bathrooms, and accommodates up to 6 guests, featuring a fully equipped kitchen with a dishwasher and microwave, plus free Wi-Fi and parking.
Ling Farm Cottage - Chesterfield
9.8 83 reviews

Ling Farm Cottage

house, Holmewood
Ling Farm Cottage is located in Holmewood, a peaceful village just 22 kilometres from Sherwood Forest and within easy reach of Chatsworth House, Clumber Park, and FlyDSA Arena. It has received excellent ratings for its cleanliness, location, and overall experience.
This two-bedroom holiday home comfortably sleeps four guests and provides a private garden, a fully equipped kitchen with a dishwasher, free Wi-Fi, and free parking. You can enjoy a peaceful retreat in the garden or explore the nearby attractions.

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.

Popular destinations

Discover Holiday Rentals with a Balcony in Chesterfield

Relax outdoors and watch the town come alive from the elevated vantage of holiday rentals with a balcony in Chesterfield.

Amber Cabin - Chesterfield
8.8 11 reviews

Amber Cabin

cabin, Ashover
Amber Cabin, a self-catering lodge in Ashover, is situated 12.4 kilometres from Chatsworth House and 32.2 kilometres from Utilita Arena Sheffield.
This 70 square metre lodge accommodates up to 7 guests across 2 bedrooms and 2 bathrooms, featuring a garden, terrace, WiFi, and private parking, with a kitchen and living area with a fireplace.
1885 The Retreat - Chesterfield
9.3 27 reviews

1885 The Retreat

apartment, Matlock
This 19th-century flat is located in a historic building in Matlock, offering convenient access to Chatsworth House (12 kilometres) and Alton Towers (35 kilometres).
This 35 square metre flat accommodates up to five guests, featuring one bedroom, a fully equipped kitchen, free WiFi, and a terrace, with pets welcome.
1 Coach House Mews - Matlock Bath - Chesterfield
9.7 224 reviews

1 Coach House Mews - Matlock Bath

apartment, Matlock Bank
This apartment is located in the quiet district of Matlock Bank, just 10 miles from Chatsworth House and 22 miles from Buxton Opera House, making it an ideal base for exploring the Peak District. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property offers two bedrooms and two bathrooms, providing comfortable accommodation for up to four guests. The 70 square metre apartment features a fully equipped kitchen, a terrace with inner courtyard views, free parking, and free Wi-Fi, allowing you to relax and enjoy your stay.
Dogs Welcome Peaks Retreat Views 3br Sleep 5 - Chesterfield
9.1 7 reviews

Dogs Welcome Peaks Retreat Views 3br Sleep 5

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.

Best Chesterfield holiday rentals with air conditioning

Hip Hideaway In The Trendiest Part Of Town - Chesterfield
9.7 6 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.
Riber Hall - Chesterfield
9.6 113 reviews

Riber Hall

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 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.
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.

Book Your Next Luxury Holiday Rental in Chesterfield

Find luxury holiday rentals in Chesterfield for a stylish, high-end city stay.

Barlow Country Club - Mill Farm Cottages - Chesterfield
9.8 5 reviews

Barlow Country Club - Mill Farm Cottages

house, Barlow

Browse Downtown Holiday Rentals in Chesterfield

Spend less time on public transport and more time visiting nearby sights from centrally located holiday rentals in Chesterfield.

College View - Chesterfield
9.8 16 reviews

College View

apartment
9nqs
A Comfortable Home In Chesterfield - Chesterfield
9.9 19 reviews

9nqs A Comfortable Home In Chesterfield

apartment
Lv8 Chesterfield - Chesterfield
9.6 5 reviews

Lv8 Chesterfield

apartment, Chesterfield
Spire Haven - Chesterfield
9.9 23 reviews

Spire Haven

house, Chesterfield
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