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?

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 among 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?

Among the Airbnbs in Chesterfield, 3 Bedroom House Near Woods - Edge Of Peak District , The Long Hall 2 Bed Ground Floor Annexed Apartment and New Hall House - Peak District are the most popular ones.

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?

The best rentals for families and kids in Chesterfield are 3 Bedroom House Near Woods - Edge Of Peak District , The Barn At Woodland View and 'Rose House' Modern 3 Bedroom Detached House .

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.

Chesterfield Holiday Rentals and Airbnb

No reviews

Stylish Home Close 2 City Centre & Rail Station

apartment, Sheepbridge and Whittington Moor Station

This spacious 140 square meter flat is located in Sheepbridge and Whittington Moor Station, offering excellent transport links to Sheffield city centre and the rail station, with Sheffield city centre being 3.7 kilometers away.
This one-bedroom flat accommodates up to 7 guests with two bathrooms, a fully equipped kitchen including a fridge and microwave oven, and complimentary WiFi, making it ideal for both leisure and business stays.

No reviews

Home From Home | 2-bed Chesterfield Stay

apartment, Brimington

This Brimington flat is situated in Chesterfield, offering convenient access to Chatsworth House (12 kilometers away), Barrow Hill Roundhouse Railway Centre (3 kilometers away), Sheffield (24 kilometers away), and the Peak District National Park.
This two-bedroom residence accommodates up to four guests, featuring a fully equipped kitchen, a modern bathroom with a walk-in shower, complimentary Wi-Fi, and on-site parking, making it ideal for both short and extended stays.

9.8 32 reviews

Little Hive-uk39430

house, Dronfield

Little Hive-UK39430, a self-catering holiday home in Dronfield, is conveniently located 13.5 km from the Utilita Arena Sheffield and 17.7 km from Chatsworth House, offering easy access to other attractions within a 40 km radius.
This one-bedroom property sleeps a couple or small group, boasting a fully equipped kitchen with a dishwasher, free Wi-Fi, private parking, and a private entrance; guests can enjoy a peaceful getaway close to Sheffield and the Peak District.

8.1 69 reviews

3 Bedroom House, Close To Woodland, Chesterfield And Peak District

house, Brimington

This charming house is situated in Brimington, just 14 km from Chatsworth House and 15 km from FlyDSA Arena, offering easy access to the Peak District and its stunning scenery. The property has received excellent ratings for its cleanliness, location, and overall experience.
The house is a comfortable and spacious 121 square meter property with one bedroom, one bathroom and can accommodate up to five guests. Guests can enjoy a fully equipped kitchen, a relaxing garden, and on-site parking, along with other amenities like a flat-screen TV and Wi-Fi.

9.6 45 reviews

The Blossoms - Studio Apartment

apartment

This Chesterfield studio apartment offers convenient ground-floor access and a private entrance, situated a short walk from Chesterfield railway station and the town centre, providing easy access to the Peak District National Park. This Derbyshire self-catering unit sleeps two guests and includes a well-equipped kitchenette with a fridge, microwave, kettle, toaster, and coffee press, plus a designated workspace and fast broadband.

8.3 24 reviews

Cuckoo Nest

house, Chesterfield

Cuckoo Nest, a self-catering house in Chesterfield, is situated approximately 13.8km from Chatsworth House and within a 37-55km radius of attractions including the Utilita Arena Sheffield, Buxton Opera House, and Nottingham Castle.
This one-bedroom property boasts 90 square metres of floor space, including a fully equipped kitchen with dishwasher, a private garden, free Wi-Fi, and private parking, ideal for couples seeking a peaceful retreat with opportunities for cycling nearby.

10 29 reviews

Ellie's Place

apartment

This one-bedroom flat in Chesterfield offers a prime location on the edge of the Peak District National Park, just 3.2 kilometres from Holmebrook Valley Country Park and a 3.2 kilometre drive to Chesterfield town centre, with Chatsworth House 16 kilometres and Bakewell 20 kilometres away.
This dog-friendly accommodation for two guests includes a private garden, driveway parking, internet, a kitchen, and a Smart TV, making it ideal for exploring Derbyshire's attractions.

No reviews

Cottage ∙ 2 Bedrooms ∙ 6 Guests

cottage, Kelstedge

This Peak District cottage in Kelstedge is conveniently located above a local pub, offering easy access to the Peak District National Park's walking trails and attractions, though precise distances to specific landmarks aren't provided.
Sleeping up to six guests, the self-catering property comprises two bedrooms (one double with en-suite, one twin), two bathrooms, a well-equipped kitchen, a living room with a sofa bed and Freeview TV, plus free Wi-Fi and parking for two cars; dogs are welcome.

9.9 27 reviews

Barn Owls Nest-uk39432

house, Dronfield

Barn Owls Nest, a one-bedroom house in Dronfield, Derbyshire, is conveniently located 13.5 km from Sheffield's Utilita Arena and 17.7 km from Chatsworth House.
This self-catering property sleeps three, boasts a fully equipped kitchen, free Wi-Fi, private parking, and a fireplace; nearby attractions include Buxton Opera House (38.6km).

9.1 13 reviews

The Gatehouse-uk11836

house, Dronfield

The Gatehouse-uk11836 is located in Dronfield, a short drive from Chatsworth House, Clumber Park, and FlyDSA Arena, making it ideal for exploring the region. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom home comfortably accommodates up to four guests. The property features a private garden, free parking, and modern amenities like Wi-Fi, a fully equipped kitchen, and a washing machine.

No reviews

Brampton Terrace: Long Stays, Chesterfield Town

apartment

This two-bedroom flat in Chesterfield's S40 postcode is located within 500 meters of Chatsworth Road and a short distance from the Peak District.
This property accommodates up to six guests and features a kitchen-diner, a separate living room with a sofa bed, a private yard accessible via a shared walkway, and free on-street parking.

10 204 reviews

Ritas Retreat

gîte

Rita's Retreat is situated in the Derbyshire countryside, just a 10-kilometre drive from the Peak District National Park, offering scenic views and a peaceful escape. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This self-catering cottage sleeps two guests and features a comfortable living area with a Smart TV, a well-equipped kitchen, and a private decking area with a fire pit. Guests can enjoy a range of activities in the surrounding area, including hiking, cycling, and exploring the charming villages and historic sites of the Peak District.

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.

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.

No reviews

Cottage ∙ 1 Bedroom ∙ 3 Guests

cottage, Barlow

This Barlow holiday cottage is situated within 50 acres of conservation pastures and woodland, offering a tranquil natural environment close to the Peak District National Park and the South Yorkshire border.
This one-bedroom lodge accommodates up to three guests and features an open-plan living space with a gas fire, a zip and link super kingsize bed, complimentary Wi-Fi, and a patio with shared garden furniture, ideal for bird and wildlife spotting.

No reviews

Mill Farm Cottages - Cherry Tree

cottage, Barlow near Bakewell

This two-bedroom holiday cottage in Barlow Country Park, Derbyshire, is located on the edge of the Peak District National Park and near the South Yorkshire border, offering proximity to Abbeydale Industrial Hamlet and Barrow Hill Roundhouse Railway Centre.
This pet-friendly lodge accommodates four guests with an open-plan living space, a private garden, and on-site fishing lakes within 50 acres of conservation pastures and woodland, providing a unique base for exploring the Peak District.

10 282 reviews

'Rose House' Modern 3 Bedroom Detached House

apartment

This apartment is located just 1.6km from Chesterfield town centre, making it easy to access shops, restaurants and local amenities, and is within a 15-minute drive of Chatsworth House, Haddon Hall and the Peak District National Park. It has consistently received excellent ratings for location, cleanliness and user experience.
The flat has an open-plan living area, kitchen and dining space, accommodating up to 6 guests in two double bedrooms and a single room with bunk beds. The property also benefits from a private garden, parking and internet access, making it a comfortable and convenient base for exploring Derbyshire.

Best Chesterfield holiday rentals with parking

8.4 95 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.

9.0 403 reviews

Barlow Country Club - Mill Farm Cottages

house, Dronfield

Barlow Country Club - Mill Farm Cottages is located in Dronfield, just a short drive from Chatsworth House and FlyDSA Arena, offering a peaceful retreat in the countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottages are family-friendly and pet-friendly, featuring a garden, terrace, and a restaurant on-site. Guests can enjoy free Wi-Fi, a fully equipped kitchen, and a tennis court, making it ideal for a relaxing and enjoyable stay.

10 4 reviews

2 Bedroom Accommodation In Holymoorside

cottage, Holymoorside

This charming cottage is located just 5 kilometres from the Peak District National Park, offering easy access to the stunning scenery and walking trails of the area. It's also within easy reach of Chesterfield, with its historic market and museums, as well as Queen's Park and Mecca Bingo for entertainment.
The cottage has two bedrooms and can accommodate up to four guests. It comes equipped with modern amenities, including a washing machine, TV, and a kitchen with a dishwasher, as well as a private garden for relaxing and enjoying the fresh air.

9.5 64 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Barrow Hill

This Barrow Hill cottage, a former grocery store, is centrally located, a short walk from the Chesterfield Canal, Cuckoo Way, and the Trans-Pennine Trail, and a short drive (approx. 5km) from Chesterfield town centre and its attractions, including the Crooked Spire church and Queens Park.
The 130 square metre self-catering property sleeps six across three bedrooms, boasting a cosy sitting room with gas fire, a large garden ideal for children, and a fully equipped kitchen including a fridge, microwave, and dishwasher; nearby amenities include a children's playground and excellent access to walking and cycling trails.

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?
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 among 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?
Among the Airbnbs in Chesterfield, 3 Bedroom House Near Woods - Edge Of Peak District, The Long Hall 2 Bed Ground Floor Annexed Apartment and New Hall House - Peak District are the most popular ones.
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?
The best rentals for families and kids in Chesterfield are 3 Bedroom House Near Woods - Edge Of Peak District, The Barn At Woodland View and 'Rose House' Modern 3 Bedroom Detached House.
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.

No reviews

Brampton Terrace Chesterfield Centre & Peaks

apartment, Chesterfield

This Chesterfield flat is located 16 kilometres from Chatsworth House and 24 kilometres from Utilita Arena Sheffield, with East Midlands Airport 56 kilometres away.
This 70 square metre apartment offers one bedroom, one bathroom, and accommodates up to eleven guests, featuring a fully equipped kitchen, a terrace with city views, and free WiFi.

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.

8.1 39 reviews

Central Sheffield Stay, Work Trips, Contractors & City Breaks

house, Sheffield

This stylish Sheffield city centre apartment is less than 0.8km from the city centre, 6.4km from the Utilita Arena Sheffield, and offers convenient on-site parking.
The 70 square metre property features one bedroom, one bathroom, sleeps five guests, and includes a fully equipped kitchen, private terrace, garden, and free Wi-Fi.

9.4 103 reviews

The Carriage House

apartment, Matlock

The Carriage House is a charming apartment in Matlock, just 16km from Chatsworth House, 35km from Buxton Opera House, and 38km from Alton Towers. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment has one bedroom, one bathroom, and can accommodate up to two guests in its 25 square metres of space. It comes equipped with free Wi-Fi, a fully equipped kitchen, and a private terrace with garden views, allowing guests to enjoy a comfortable and convenient stay.

Best Chesterfield holiday rentals with air conditioning

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.

9.0 8 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.

9.2 23 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.

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.

Book Your Next Luxury Holiday Rental in Chesterfield

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

9.4 13 reviews

Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District

house, Brimington

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.

9.8 22 reviews

The Old Dance Studio

apartment

10 4 reviews

Lv8 Chesterfield

apartment, Chesterfield

10 1 review

Canal Mews | Chesterfield & Peak District.

apartment

9.9 19 reviews

9nqs A Comfortable Home In Chesterfield

apartment

Vacation Rentals in Chesterfield

193 Holiday rentals and Airbnb in Chesterfield

Stylish Home Close 2 City Centre & Rail Station

Home From Home | 2-bed Chesterfield Stay

Little Hive-uk39430

3 Bedroom House, Close To Woodland, Chesterfield And Peak District

The Blossoms - Studio Apartment

Cuckoo Nest

Ellie's Place

Cottage ∙ 2 Bedrooms ∙ 6 Guests

Barn Owls Nest-uk39432

The Gatehouse-uk11836

Brampton Terrace: Long Stays, Chesterfield Town

Ritas Retreat

Cottage ∙ 2 Bedrooms ∙ 4 Guests

Cottage ∙ 1 Bedroom ∙ 3 Guests

Mill Farm Cottages - Cherry Tree

'Rose House' Modern 3 Bedroom Detached House

Bolsover Castle View

Barlow Country Club - Mill Farm Cottages

2 Bedroom Accommodation In Holymoorside

Cottage ∙ 3 Bedrooms ∙ 6 Guests

Brampton Terrace Chesterfield Centre & Peaks

Hip Hideaway In The Trendiest Part Of Town

Central Sheffield Stay, Work Trips, Contractors & City Breaks

The Carriage House

Riber Hall

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

Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre

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

Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District

The Old Dance Studio

Lv8 Chesterfield

Canal Mews | Chesterfield & Peak District.

9nqs A Comfortable Home In Chesterfield