What should a first-time visitor not miss in Chesterfield?

You've got to see the Crooked Spire, it's a real icon of Chesterfield. The town's museum is also brilliant, you'll learn all about the history of the area. And if you're into gardens, the Queen's Park is a must-see.

What are the best Airbnb and vacation 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 the most popular Airbnb and vacation rentals in Chesterfield among travelers.

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

The town centre is great for being near the shops and restaurants, but if you want a bit more peace and quiet, try the areas around Queen's Park or Walton.

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.

What are the top family-friendly attractions in Chesterfield?

The Chesterfield Museum and Art Gallery is great for kids, they have lots of interactive exhibits. The Chesterfield Canal is also brilliant for a family walk or bike ride, and you can even hire a boat.

What are the best vacation rentals with a pool in Chesterfield?

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

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

If you want to avoid the crowds, book your rental outside of school holidays. The summer months are always busy, so booking in advance is essential.

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

The Chesterfield Food and Drink Festival is always a hit, and there's also the Chesterfield Beer Festival in the autumn. For something a bit different, check out the Chatsworth Country Fair, it's just a short drive away.

What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?

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

What are the best budget-friendly activities in Chesterfield?

A walk along the Chesterfield Canal is free and offers beautiful views. You can also visit the Queen's Park, which is a great place to relax and enjoy the outdoors.

What are the best restaurants with local dishes in Chesterfield?

The Old Vicarage is a popular choice for traditional pub grub, and you can't go wrong with The Little Chef for a classic British breakfast. For something a bit fancier, try The Tap, they do a great Sunday roast.

What are the best walking or cycling routes in Chesterfield?

The Chesterfield Canal towpath is a lovely walk, and there are plenty of cycling routes through the Peak District National Park nearby. The Chesterfield to Staveley cycle path is a good option.

Are there pet-friendly attractions in Chesterfield?

The Queen's Park is dog-friendly, and many of the pubs and restaurants in the town centre welcome dogs too. The Chesterfield Canal towpath is also great for walking your dog.

What are the benefits of choosing a vacation rental in Chesterfield?

Vacation rentals offer more space and privacy than a hotel, and you can often find rentals with unique features, like a garden or a hot tub. They are also often a more affordable option, especially for families or groups.

What are the top sports attractions and facilities in Chesterfield?

The Proact Stadium is home to Chesterfield FC, and the town has a number of other sports facilities, including a bowling alley, a leisure centre, and a golf course.

Best Vacation Rentals & Airbnb in Chesterfield for 2026

10 15 reviews

1 Bedroom Accommodation In Old Brampton, Near Chesterfield

cottage, Old Brampton, near Chesterfield

This cottage is located in a rural area near Chesterfield, offering convenient access to Chatsworth House and the Peak District National Park.
This pet-friendly holiday let accommodates two guests with one bedroom and one bathroom, featuring Wi-Fi, a garden, and proximity to walking routes and local amenities including a pub just 400 meters away.

8.9 89 reviews

Woodfield Retreat

apartment, Matlock

Woodfield Retreat, a one-bedroom apartment in Matlock, Derbyshire, is conveniently located 13km from Chatsworth House and offers easy access to the Peak District National Park.
This self-catering flat sleeps three, features a fully equipped kitchenette with microwave and fridge, private parking, free Wi-Fi, and an outdoor dining area; towels and bed linen are provided.

10 1 review

2 Bedroom Accommodation In Matlock

cottage, Matlock

This Matlock riverside cottage, situated within 10km of attractions including Lumsdale Valley, Crown Square, Hall Leys Park, Matlock Bath Parks Country Park, and the Life in a Lens Museum, offers a tranquil escape.
Sleeping up to six guests in two bedrooms and two bathrooms, the self-catering property includes free parking, Wi-Fi, a fully equipped kitchen with a fridge and oven, and a TV; pets are welcome.

9.9 332 reviews

Chatsworth Cottage

apartment

This charming cottage is located on the edge of the Peak District National Park, just 10 kilometres from Chatsworth House and a 20-minute walk from Chesterfield town centre. The property boasts excellent user, location and cleanliness ratings, making it an ideal choice for travellers seeking a comfortable and convenient stay.
The cottage comfortably sleeps five guests in two bedrooms and one bathroom. It features a fully equipped kitchen, a cosy living room with a fireplace, a beautiful garden and patio area, and modern conveniences such as super-fast Wi-Fi and a Smart TV.

9.8 70 reviews

Vale Barn

house, Dronfield

Vale Barn is a holiday home located in Dronfield, just 14km from FlyDSA Arena and 19km from Chatsworth House, offering easy access to these popular attractions. This property has received excellent ratings for location, cleanliness and overall user experience.
The two-bedroom property is 105 square metres in size and comfortably accommodates a small family or group of friends. Guests can enjoy a fully equipped kitchen, a relaxing garden, free Wi-Fi, private parking and a terrace, making Vale Barn a great choice for a relaxing and enjoyable stay in Dronfield.

9.6 21 reviews

Round House View

house, Chesterfield

Round House, a Brimington house, is conveniently located 21km from Chatsworth House and the Utilita Arena Sheffield.
This 61 square metre property sleeps nine guests and boasts a fully equipped kitchen, private terrace, garden, parking, and Wi-Fi; a washing machine is also provided.

10 1 review

1 Bedroom Accommodation In Dronfield

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.

9.6 202 reviews

Beautiful Grade Ii Listed Gatehouse In Great Location

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.

9.5 14 reviews

Smithy Cottage

house, Dronfield

Smithy Cottage, a two-bedroom house in Dronfield, Derbyshire, enjoys a peaceful location 14.8 km from Chatsworth House, 22.5 km from Sheffield, and 35.4 km from Buxton.
This 105 square metre property sleeps seven, boasting a fully equipped kitchen with dishwasher, garden, parking, free Wi-Fi, and a fireplace; pets are welcome.

10 63 reviews

Crossfield Coach House

apartment

This Derbyshire annex, located ten minutes (approx. 16km) from the M1 motorway and within walking distance of local amenities, offers a convenient base for exploring the county.
The self-contained apartment sleeps two guests and features a private upstairs annex with separate lounge, bedroom, fully equipped kitchen, patio with barbecue, and secure parking behind electric gates.

No reviews

The Painted Terrace - Peaceful Home In Calow Near The Royal Hospital

house, Chesterfield

This spacious holiday home is located in Chesterfield, 19 kilometres from Chatsworth House, 22 kilometres from Utilita Arena Sheffield, and 35 kilometres from Sherwood Forest.
This one-bedroom property offers accommodation for up to seven guests, featuring a private garden, terrace, fireplace, and free on-site parking, with WiFi also provided.

9.0 2 reviews

2 Bed Apartment In Chesterfield With Free Parking - Sleeps Upto 5 - Perfect For Workers & Professionals - Hosted By Stayhostsave

apartment, Chesterfield

This centrally located flat in Chesterfield offers convenient access to local amenities and attractions, situated within the town's central district.
This accommodation provides two bedrooms, two bathrooms, a fully equipped kitchen, and complimentary Wi-Fi, accommodating up to nine guests for a non-smoking stay with no parties.

Best family friendly Chesterfield vacation rentals

Among the 193 accommodations in Chesterfield, here are the 4 best family friendly rentals

10 341 reviews

Wasp Nest Cottage, Peak District

apartment

This charming 19th-century cottage is located on the edge of the Peak District, just 3.5 km from Chatsworth House and a short walk from two pubs and a shop. It has received excellent ratings for location, cleanliness, and overall experience.
The cottage sleeps up to four guests and offers a master bedroom with a double bed, a snug cabin room with a double bed, and a sofa bed in the sitting room. Guests can enjoy a fully equipped kitchen, a cosy sitting room, a conservatory, and a small garden patio with a table and chairs.

9.7 17 reviews

Stone Cottage

house, Wingerworth

Stone Cottage, a four-star self-catering property in Wingerworth, Derbyshire, is ideally located within 19-43km of Chatsworth House, Sherwood Forest, and Sheffield.
This one-bedroom holiday home offers free private parking, Wi-Fi, a fully equipped kitchen, and a private garden, perfect for couples or solo travellers seeking a peaceful retreat near major attractions.

10 3 reviews

2 Bed House - Near Central Sheffield - Fast Wi-fi

apartment, Sheffield

This 2-bedroom flat is situated in Sheffield, approximately 4.65 kilometres from the Utilita Arena and 24.14 kilometres from Chatsworth House.
This family-friendly property offers space for up to five guests, featuring a fully equipped kitchen, complimentary high-speed Wi-Fi, and free private parking, with a floor area of 12 square meters.

8.9 39 reviews

The Loft At The George

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 vacation rentals with parking

9.5 43 reviews

2 Snape Hill

house, Dronfield

2 Snape Hill is a holiday home in Dronfield, just 14 km from FlyDSA Arena, 19 km from Chatsworth House, and 36 km from Clumber Park, making it a great base for exploring the Peak District. Guests consistently rate the property excellent for its location, cleanliness, and overall experience.
This three-bedroom property offers 130 square metres of space, comfortably accommodating up to six guests. The house has a fully equipped kitchen with a fridge, microwave, and dishwasher, a garden, parking, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

8.8 11 reviews

3 Bedroom Home In Chesterfield With Front And Back Gardens

apartment, Chesterfield

This three-bedroom Chesterfield apartment, ideally located for exploring the Peak District, is just 16km from Chatsworth House and 24km from the FlyDSA Arena.
The self-catering property boasts a fully equipped kitchen, private parking, free WiFi, two gardens, and comfortably accommodates up to 13 guests, with a complimentary welcome drink upon arrival.

9.9 146 reviews

Peak Edge Terrace (Derbyshire, Peak District)

house

Peak Edge Terrace is located on the eastern edge of the Peak District, just 15 kilometers from Chatsworth House and a 20-minute walk from Chesterfield, offering a peaceful retreat in a beautiful setting. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The house comfortably accommodates up to six people with two bedrooms, a bathroom, a spacious living room, and a dedicated games room. Guests can enjoy a fully equipped kitchen, a private courtyard with garden furniture, and a range of amenities for both adults and children, including a Smart TV, board games, and access to local information.

9.9 40 reviews

Cosy 2 Bed Home Chesterfield

apartment, Chesterfield

This apartment is located in Chesterfield, just 21 km from Chatsworth House and 22 km from FlyDSA Arena, offering a peaceful setting with garden views. The property has received excellent ratings for cleanliness, location, and overall experience.
The home features two bedrooms, one bathroom, and a floor area of 50 square metres, accommodating up to four guests. Amenities include a kitchen with a fridge, freezer, and microwave, as well as internet access, parking, and a garden.

Frequently Asked Questions about vacation rentals in Chesterfield

What should a first-time visitor not miss in Chesterfield?
You've got to see the Crooked Spire, it's a real icon of Chesterfield. The town's museum is also brilliant, you'll learn all about the history of the area. And if you're into gardens, the Queen's Park is a must-see.
What are the best Airbnb and vacation 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 the most popular Airbnb and vacation rentals in Chesterfield among travelers.
Which neighborhood in Chesterfield should you consider for a vacation rental?
The town centre is great for being near the shops and restaurants, but if you want a bit more peace and quiet, try the areas around Queen's Park or Walton.
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.
What are the top family-friendly attractions in Chesterfield?
The Chesterfield Museum and Art Gallery is great for kids, they have lots of interactive exhibits. The Chesterfield Canal is also brilliant for a family walk or bike ride, and you can even hire a boat.
What are the best vacation rentals with a pool in Chesterfield?
Manor House, Family Fun Party House Pool - Bar - Sauna - Cinema and Tawny Owl Barn are the best vacation rentals with a pool in Chesterfield.
When is the best time to book a vacation rental in Chesterfield?
If you want to avoid the crowds, book your rental outside of school holidays. The summer months are always busy, so booking in advance is essential.
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 events or festivals should visitors check out in and around Chesterfield?
The Chesterfield Food and Drink Festival is always a hit, and there's also the Chesterfield Beer Festival in the autumn. For something a bit different, check out the Chatsworth Country Fair, it's just a short drive away.
What are the best rentals or Airbnbs with a jacuzzi in Chesterfield?
The best vacation rentals or Airbnb with a jacuzzi in Chesterfield are Spapartyhome With Hottub Sauna Bbq & Pool Table, Manor House and Hot Tub House Close To Woodland And Peak District.
What are the best budget-friendly activities in Chesterfield?
A walk along the Chesterfield Canal is free and offers beautiful views. You can also visit the Queen's Park, which is a great place to relax and enjoy the outdoors.
What are the best restaurants with local dishes in Chesterfield?
The Old Vicarage is a popular choice for traditional pub grub, and you can't go wrong with The Little Chef for a classic British breakfast. For something a bit fancier, try The Tap, they do a great Sunday roast.
What are the best walking or cycling routes in Chesterfield?
The Chesterfield Canal towpath is a lovely walk, and there are plenty of cycling routes through the Peak District National Park nearby. The Chesterfield to Staveley cycle path is a good option.
Are there pet-friendly attractions in Chesterfield?
The Queen's Park is dog-friendly, and many of the pubs and restaurants in the town centre welcome dogs too. The Chesterfield Canal towpath is also great for walking your dog.
What are the benefits of choosing a vacation rental in Chesterfield?
Vacation rentals offer more space and privacy than a hotel, and you can often find rentals with unique features, like a garden or a hot tub. They are also often a more affordable option, especially for families or groups.
What are the top sports attractions and facilities in Chesterfield?
The Proact Stadium is home to Chesterfield FC, and the town has a number of other sports facilities, including a bowling alley, a leisure centre, and a golf course.

Popular destinations

Best Chesterfield vacation rentals with a balcony

9.6 384 reviews

Jewel Cottage

house, Matlock

Jewel Cottage is situated on the edge of the Peak District National Park, just a short walk from the Victorian Spa town of Matlock, 8km from Chatsworth House and a 30-minute drive from Hardwick Hall. This charming cottage has consistently received excellent ratings for its location, cleanliness, and overall experience.
Jewel Cottage offers 2 bedrooms and 1 bathroom across 20 square metres. Guests can enjoy a fully equipped kitchen, a garden, a terrace, free parking, and free WiFi, making it an ideal base for exploring the Peak District and the surrounding area.

No reviews

Farmhouse ∙ 5 Bedrooms ∙ 10 Guests

farm, Marsh Lane

Habberjam Farm is a 17th-century property situated in the Peak District, offering direct access to forest walks and countryside trails, with Sheffield and the Peak District National Park both a 32-kilometre drive away. This 5-bedroom, 3-bathroom farmhouse accommodates up to 10 guests and features a private hot tub, games room with a PS4, and an outdoor fire pit, with the Fox & Hounds pub just 183 meters walk away.

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.

9.3 47 reviews

Morden House Close To City Centre & The Peaks

house, Chesterfield

This modern house is located in Chesterfield, just 24 km from Nottingham and 9.3 km from Sheffield, offering easy access to both cities and the scenic Peak District. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The property features 3 bedrooms, comfortably accommodating up to 6 guests, and spans 139 square metres. The house is equipped with a range of amenities, including a fully equipped kitchen, a terrace, a garden, a spa, parking, and concierge services.

Best Chesterfield vacation rentals with air conditioning

No reviews

Thesignature# Groups #Contractors #Parking #Wi-fi

apartment

This executive suite in Chesterfield is located near the city centre, offering a 5-minute walk to supermarkets and the hospital, and is 3.06 kilometres from the train station.
This spacious apartment features four bedrooms, two and a half bathrooms, and accommodates up to six guests with versatile sleeping arrangements, including air conditioning and on-site parking via a garage and driveway, ideal for contractors and groups seeking long stays with weekly and monthly booking discounts.

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.

10 1 review

Spacious 4 Bed Home For Families & Contractors.

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.

9.1 12 reviews

Affordable 1br Flat By Ankers Short Term Lets Matlock Bath With Exclusive Summer Savings

apartment, Matlock Bank

This Matlock Bank apartment is conveniently located 14km from Chatsworth House, 32km from Alton Towers, and 34km from Buxton Opera House, offering easy access to the Peak District National Park.
Sleeping six guests, this self-catering flat boasts a king-size bed, a fully equipped kitchen, free Wi-Fi, air conditioning, parking, and one bathroom.

Compare Vacation Rentals & Airbnb in Chesterfield

193 Rentals and Airbnb in Chesterfield

1 Bedroom Accommodation In Old Brampton, Near Chesterfield

Woodfield Retreat

2 Bedroom Accommodation In Matlock

Chatsworth Cottage

Vale Barn

Round House View

1 Bedroom Accommodation In Dronfield

Beautiful Grade Ii Listed Gatehouse In Great Location

Smithy Cottage

Crossfield Coach House

The Painted Terrace - Peaceful Home In Calow Near The Royal Hospital

2 Bed Apartment In Chesterfield With Free Parking - Sleeps Upto 5 - Perfect For Workers & Professionals - Hosted By Stayhostsave

Best family friendly Chesterfield vacation rentals

Wasp Nest Cottage, Peak District

Stone Cottage

2 Bed House - Near Central Sheffield - Fast Wi-fi

The Loft At The George

Best Chesterfield vacation rentals with parking

2 Snape Hill

3 Bedroom Home In Chesterfield With Front And Back Gardens

Peak Edge Terrace (Derbyshire, Peak District)

Cosy 2 Bed Home Chesterfield

Frequently Asked Questions about vacation rentals in Chesterfield

Popular destinations

Best Chesterfield vacation rentals with a balcony

Jewel Cottage

Farmhouse ∙ 5 Bedrooms ∙ 10 Guests

Home From Home | 2-bed Chesterfield Stay

Morden House Close To City Centre & The Peaks

Best Chesterfield vacation rentals with air conditioning

Thesignature# Groups #Contractors #Parking #Wi-fi

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

Spacious 4 Bed Home For Families & Contractors.

Affordable 1br Flat By Ankers Short Term Lets Matlock Bath With Exclusive Summer Savings