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.

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.
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.
Bens Green, Parking, Spacious Home, Near The Peaks - Chesterfield
No reviews

Bens Green, Parking, Spacious Home, Near The Peaks

apartment, South Yorkshire
This 4-bedroom house in Sheffield, South Yorkshire, is situated 1.26 kilometers from Bingham Park and 1.12 kilometers from Bramall Lane, offering convenient access to local attractions.
This family-friendly property accommodates up to 9 guests and features a garden, terrace, Wi-Fi, and a fully equipped kitchen, ideal for exploring Sheffield's cultural sites and shopping destinations like Meadowhall Shopping Centre.
Cottage ∙ 2 Bedrooms ∙ 3 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 3 Guests

cottage, Holymoorside
This Holymoorside holiday cottage, a renovated barn conversion, is situated in Derbyshire, on the edge of the Peak District National Park, approximately 16km from Bakewell and within easy driving distance of Matlock, Matlock Bath, and Chesterfield.
The self-catering property boasts two bedrooms sleeping three guests, a fully equipped kitchen with a dishwasher, a private courtyard, private parking for two cars and two motorcycles, and is close to three churches and two pubs, one serving Peak Ales.

Best Chesterfield holiday rentals with parking

Commuters Getaway Chesterfield - Chesterfield
10 2 reviews

Commuters Getaway Chesterfield

house, Chesterfield
This apartment is situated in Chesterfield, just a 15-minute walk from Queen's Park, Mecca Bingo, and Chesterfield Market, and within 2km of Chesterfield Museum & Art Gallery and Pomegranate Theatre, making it ideal for exploring the town's attractions. The property is located in a quiet area, offering a peaceful retreat from the town centre.
The apartment features a kitchen equipped with a fridge and microwave oven, as well as a garden and a jacuzzi for relaxation. Guests can also enjoy free parking and Wi-Fi, ensuring a comfortable and convenient stay.
Old Barn Conversion Close To The Peak District - Chesterfield
9.7 299 reviews

Old Barn Conversion Close To The Peak District

apartment
The Barn At Woodland View is located in Barlow, a short drive from Sherwood Forest, Nottingham Castle, and Chatsworth House, making it a great base for exploring the region's historical attractions. The property has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The house has two bedrooms and one bathroom, comfortably accommodating up to four guests. It comes equipped with a kitchen featuring a fridge, freezer, and microwave oven, along with free Wi-Fi, a washing machine, and private parking.
Blissful Barrys - Chesterfield
9.7 42 reviews

Blissful Barrys

apartment
This three-bedroom house in Brimington enjoys a peaceful cul-de-sac location on the edge of the Peak District National Park, a 10-minute drive from Chesterfield town centre and its Crooked Spire.
Sleeping up to five guests in two double bedrooms and one single, the property offers free parking, Wi-Fi, a microwave, and is within walking distance of local pubs and an Indian restaurant, with the Chesterfield Canal a short stroll away.
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.

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.

Sheffield City Centre Apartment & Balcony - Chesterfield
9.7 208 reviews

Sheffield City Centre Apartment & Balcony

apartment, Sheffield
This Sheffield city centre flat is located less than 0.6km from the city centre, 6.4km from the Utilita Arena, and between 26 and 42km from Chatsworth House, Eco-Power Stadium, Cusworth Hall, and Buxton Opera House.
The 54 square metre apartment offers two bedrooms, one bathroom, sleeps four guests, and includes a private balcony, secure parking, a well-equipped kitchen, and free Wi-Fi.
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.
Studio 77 - Stylish, Free Parking, Fast Wi-fi, Netflix - Chesterfield
9.4 62 reviews

Studio 77 - Stylish, Free Parking, Fast Wi-fi, Netflix

studio, Sheffield
Studio77 Sheffield is situated 5 kilometres from the Utilita Arena Sheffield, offering convenient access by car to Chatsworth House, Clumber Park, and Cusworth Hall.
This 25 square metre studio flat sleeps two guests and features a fully equipped kitchen, terrace, garden, free parking, and free Wi-Fi.
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.

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.
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.
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.
Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre - Chesterfield
9.2 22 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.

Book Your Next Luxury Holiday Rental in Chesterfield

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

The Corner House - Chesterfield
9.7 3 reviews

The Corner House

house, Chesterfield

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.

Spire View | Chesterfield 2 Bedroom Apartment - Chesterfield
9.9 19 reviews

Spire View | Chesterfield 2 Bedroom Apartment

apartment
Stylish Flat In Chesterfield Peak District - Chesterfield
9.3 50 reviews

Stylish Flat In Chesterfield Peak District

apartment, Chesterfield
Town Centre Modern Apartment - Chesterfield
9.7 129 reviews

Town Centre Modern Apartment

apartment
Peak District Escape | Business & Leisure Stay - Chesterfield
10 5 reviews

Peak District Escape | Business & Leisure Stay

apartment
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