This studio flat offers a private, detached stay within a converted Victorian School campus on the outskirts of Brimington, providing a unique historical setting. This cosy and stylish self-contained unit, ideal for two guests, features a studio layout with an integrated kitchen and shower room, set within a peaceful environment with internet access.
9.8 26 reviews
Chesterfield
21/08 – 24/08
$255/nighttotal: $765 (3 )
Charming 18th Century Stone Cottage
1 2
apartment , Chesterfield
This restored circa-1800 cottage, Carpenters Mews, is situated in a peaceful corner of Newbold Village, offering exclusive access via electronic gates and a private courtyard entry, with Tesco Express and Co-op within 100 meters, and Chatsworth House and Haddon Hall within a 10 kilometer radius. This 2-bedroom, 1-bathroom apartment accommodates up to 4 guests and features characterful interiors with original beamed ceilings, a cosy lounge with a fireplace, a modern farmhouse kitchen, and a renovated bathroom, with access to a garden space with BBQ available on request, serving as an ideal base for exploring the Peak District countryside.
10 14 reviews
Chesterfield
26/06 – 28/06
$178/nighttotal: $356 (2 )
Haven Shepherds Hut
1 2
cabin , Ashover
The Shepherds Hut is located in High Ashes Haven, a short distance from the village of Ashover, which is known for its beautiful countryside and close proximity to the Peak District National Park. This charming retreat offers a peaceful escape in the heart of the Derbyshire countryside. The cosy hut has a comfortable double bed and can accommodate two guests. It is fully equipped with a private bathroom, a well-equipped outdoor kitchen with a BBQ, gas hob, and woodfired pizza oven, and a charming garden where you can relax and enjoy the fresh air.
Chesterfield
18/09 – 24/09
$142/nighttotal: $852 (6 )
Miners Cottage
1 2
house , Clowne
Miners Cottage in Clowne provides convenient access to attractions, located 22 kilometres from Clumber Park and 24 kilometres from Sherwood Forest. This 3-star rated holiday home offers one bedroom, a fully equipped kitchen with a dishwasher and washing machine, complimentary WiFi, free private parking, and a garden, with a private entrance for guest privacy.
9.8 64 reviews
Chesterfield
05/07 – 09/07
$151/nighttotal: $604 (4 )
Pet-friendly Cosy Cottage In Chesterfield
1 1
apartment , Derbyshire
This Chesterfield apartment, ideally located for exploring the Peak District and Derbyshire Dales, is within easy reach of Sheffield. The two-bedroom dwelling, sleeping up to three guests, offers a private garden, on-site parking with EV charging, and includes a picnic backpack for exploring local attractions.
9.4 22 reviews
Chesterfield
20/06 – 27/06
$135/nighttotal: $945 (7 )
Tuliptree
2 2
house , Chesterfield
Tuliptree, a Chesterfield holiday home, is peacefully situated approximately 18 kilometres from Chatsworth House and offers easy access to Sheffield, Nottingham, and Buxton. This 105 square metre property features two bedrooms, one bathroom with a walk-in shower, a fully equipped kitchen including a fridge and microwave, free Wi-Fi, and a garden with parking; nearby activities include golfing, cycling, and fishing.
9.3 9 reviews
Chesterfield
03/09 – 06/09
$218/nighttotal: $654 (3 )
1 Bed In Chesterfield Oc-dcelm
1 2
house , Old Brampton
Elm Croft, a one-bedroom house in Old Brampton, Derbyshire, is conveniently located 11km from Chatsworth House and offers easy access to other attractions like the Utilita Arena Sheffield (29km) and Buxton Opera House (32km). This self-catering property sleeps three, boasting a fully equipped kitchen with dishwasher, washing machine, free Wi-Fi, free private parking, and a cosy fireplace; enjoy peaceful surroundings and explore the local area.
9.7 172 reviews
Chesterfield
03/09 – 06/09
$206/nighttotal: $618 (3 )
2-bed Cottage - Sleeps4 - Garden - Bbq
2 2
house , Tibshelf
This Derbyshire cottage in Tibshelf offers pet-friendly accommodation, conveniently located approximately 27 kilometres from Sherwood Forest and 29 kilometres from Nottingham Castle. The 80 square metre property features two bedrooms, one bathroom, a fully equipped kitchen including a dishwasher, free Wi-Fi, private parking, and a private patio garden; ideal for exploring nearby attractions such as Chatsworth House and the National Ice Centre (both within 30km).
9.0 2 reviews
Chesterfield
03/09 – 06/09
$336/nighttotal: $1008 (3 )
1 Bed In Dronfield Oc-40971
1 2
house , Chesterfield
This one-bedroom holiday home in Barlow, Chesterfield, is situated 14km from Chatsworth House and 19km from the FlyDSA Arena. The 45 square metre property features a fully equipped kitchen, private garden, free Wi-Fi, parking, and accommodates up to three guests.
9.0 2 reviews
Chesterfield
04/07 – 08/07
$236/nighttotal: $944 (4 )
2 Bed Apartment In Chesterfield With Free Parking - Sleeps Upto 5 - Perfect For Workers & Professionals - Hosted By Stayhostsave
2 1
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.
10 15 reviews
Chesterfield
04/07 – 08/07
$168/nighttotal: $672 (4 )
Cuckoo Nest
1 1
apartment , Derbyshire
Cuckoo Nest, a self-catering cottage in Ashover, Derbyshire, is situated approximately 3.2km from a shop and 2.9km from a pub, offering easy access to the Peak District National Park. This one-bedroom property sleeps up to four guests (with a sofa bed), boasting a king-size bedroom (accessed via a ladder), a ground-floor shower room, open-plan living space with modern appliances (including a dishwasher), private driveway, and garden with decking and barbecue.
Chesterfield
01/09 – 30/11
$148/nighttotal: $13320 (90 )
Bank: Monthly Stay Near Chesterfield Town
1 1
apartment , Derbyshire
This cosy Chesterfield house, near shops, cafes and Chesterfield railway station, offers easy access to the M1 motorway and Chesterfield town centre. The two-bedroom apartment, sleeping up to six guests, includes a fully equipped kitchen-diner, high-speed Wi-Fi, a private garden, free on-site parking, and a weekly cleaning service is available.
Best family friendly Chesterfield vacation rentals
Among the 134 accommodations in Chesterfield, here are the 4 best family friendly rentals
9.8 5 reviews
Chesterfield
01/09 – 30/09
$179/nighttotal: $5191 (29 )
Unit 1 Bright & Classy 1-bdr Flat, Fast 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.
9.3 53 reviews
Chesterfield
01/09 – 30/09
$105/nighttotal: $3045 (29 )
Hill Top Cottage
1 2
apartment , Mastin Moor
Hilltop Cottage, near Junction 30 of the M1 motorway, offers easy access to Sheffield (approx. 30km), Nottingham (approx. 40km), and Chesterfield (approx. 20km), with Tesco and local pubs nearby. This two-bedroom, one-bathroom property sleeps four, boasting a fully equipped kitchen (fridge, freezer, microwave), garden, parking, internet access, and recently updated interiors including new carpets and appliances.
9.3 313 reviews
Chesterfield
03/09 – 06/09
$377/nighttotal: $1131 (3 )
Heart Of The City-flexi Cancellations-central Hub
3 2
house , Sheffield
This Sheffield property is conveniently located just 4.2 miles from FlyDSA Arena and 14 miles from Chatsworth House, making it a great base for exploring the city and surrounding areas. The house has consistently received excellent ratings for cleanliness, location, and overall user experience. The home provides ample space for families or groups of up to 8 guests, with 4 bedrooms and a comfortable living area. Guests can enjoy a fully equipped kitchen, modern amenities like a flat-screen TV and free Wi-Fi, and a relaxing patio with views of the city.
8.8 82 reviews
Chesterfield
18/09 – 24/09
$155/nighttotal: $930 (6 )
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.
Best Chesterfield vacation rentals with parking
9.8 6 reviews
Chesterfield
01/09 – 30/09
$119/nighttotal: $3451 (29 )
Spacious 3-bed Home At The Heart Of Sheffield S2
3 2
apartment , Manor
This one-bedroom flat in Manor is located in a quiet area, offering garden views and easy access to local attractions. The apartment includes a fully equipped kitchen, complimentary high-speed Wi-Fi, and a flat-screen TV, with a maximum guest capacity of 11.
10 5 reviews
Chesterfield
03/09 – 06/09
$223/nighttotal: $669 (3 )
The Old Hayloft-uk39431
1 2
cottage , Dronfield
This one-bedroom apartment is situated in Dronfield, just a short distance from the Peak District National Park, offering easy access to stunning natural landscapes. It's also conveniently located near the city of Sheffield and the historic town of Chesterfield, making it a great base for exploring the region. The self-catering property is ideal for couples or small families, with a comfortable king-size bed and a well-equipped kitchen. Enjoy the peace and quiet of the rural setting, with its 40-acre farm and over 30 horses, and take advantage of the private parking, internet access, and family-friendly amenities.
10 1 review
Chesterfield
01/09 – 30/09
$241/nighttotal: $6989 (29 )
Lovely Apartment Close 2 City Center &Rail Station
2 2
apartment , Chesterfield
This apartment is located in Chesterfield, just 1.5km from the Pomegranate Theatre, Technique Stadium, and Chesterfield Museum & Art Gallery, making it ideal for exploring the town. It has received excellent reviews from previous guests. This two-bedroom flat comfortably accommodates up to four guests. The flat offers free Wi-Fi, a Smart TV, a washing machine, and parking, ensuring a comfortable and convenient stay.
8.8 69 reviews
Chesterfield
01/09 – 30/09
$192/nighttotal: $5568 (29 )
Exquisite Central Suites Sheffield
1 2
apartment , Sheffield
This Sheffield apartment is conveniently located just 6.1 kilometres from the Utilita Arena Sheffield and 22.5 kilometres from Chatsworth House, offering easy access to both city attractions and the surrounding countryside. The one-bedroom flat, which is perfect for families, comes with a well-equipped kitchen, a private bathroom, and free Wi-Fi, providing a comfortable and convenient base for exploring Sheffield.
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?
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?
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?
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?
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.
Destinations nearby
Best Chesterfield vacation rentals with a balcony
9.1 68 reviews
Chesterfield
21/08 – 24/08
$284/nighttotal: $852 (3 )
Blue Sky Cottage
1 2
house , Matlock
Blue Sky Cottage is located in Matlock, just 14 kilometres from Chatsworth House and within a 48 kilometre radius of Buxton Opera House, FlyDSA Arena, Alton Towers, and Nottingham Castle. This well-rated cottage has received excellent reviews for its location, cleanliness, and overall experience. The cottage has one bedroom and one bathroom, offering comfortable accommodation for two guests in a 48 square metre space. Enjoy modern amenities including free Wi-Fi, a flat-screen TV, a washing machine, a fully equipped kitchen, and a peaceful terrace with private parking.
Chesterfield
20/06 – 27/06
$637/nighttotal: $4459 (7 )
Apartment ∙ 5 Bedrooms ∙ 12 Guests
5 2
apartment
This five-bedroom detached house is located on Raynald Road, Great Britain, with convenient access to Sheffield city centre via the A57 and A61, and public transport options within walking distance. This spacious accommodation, suitable for up to 12 guests, features a large open-plan living area, a fully equipped kitchen with a washer-dryer, private garden with BBQ, and driveway parking, offering flexible sleeping arrangements and self-check-in for a comfortable stay.
10 2 reviews
Chesterfield
02/07 – 06/07
$375/nighttotal: $1500 (4 )
Open Haven Collective With Man Cave And Parking 10ppl
1 1
house , Handsworth
This detached house is located in Handsworth, 4.5 kilometres from the Utilita Arena Sheffield and 27 kilometres from Chatsworth House. This property offers 79 square metres of living space with 3 bedrooms and 1 bathroom, accommodating up to 10 guests and featuring a 'Man Cave', a garden, and free private parking.
9.6 383 reviews
Chesterfield
21/08 – 24/08
$289/nighttotal: $867 (3 )
Jewel Cottage
2 2
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.
Best Chesterfield vacation rentals with air conditioning
9.0 8 reviews
Chesterfield
20/06 – 27/06
$426/nighttotal: $2982 (7 )
Superb 3 Bed House, Homely Comforts Close To Supermarkets, With Private Parking On Gated Premise
3 2
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.
Chesterfield
21/08 – 24/08
$556/nighttotal: $1668 (3 )
Lv8 Chesterfield
1 2
apartment , Chesterfield
This one-bedroom flat in Chesterfield offers proximity to Chatsworth House (16 kilometres) and Utilita Arena Sheffield (22.5 kilometres), with East Midlands Airport 56 kilometres away. This 55 square metre apartment accommodates two guests and features a fully equipped kitchen with a dishwasher, complimentary Wi-Fi, air conditioning, and private parking.
8.8 12 reviews
Chesterfield
02/07 – 06/07
$194/nighttotal: $776 (4 )
Small 1 Bed Apartment - Free Parking!!!
1 1
apartment , Victoria
This stylish one-bedroom apartment is conveniently located off City Road in Victoria, approximately 5.5km from the FlyDSA Arena and within a 30-50km radius of attractions including Chatsworth House, Eco-Power Stadium, Clumber Park, and Cusworth Hall. The 30-square-metre flat offers a private entrance, free Wi-Fi, parking, and sleeps up to five guests, boasting a fully equipped kitchen, air conditioning and a comfortable living area.
9.2 25 reviews
Chesterfield
02/07 – 06/07
$620/nighttotal: $2480 (4 )
Exceptional 3 Bed House With Homely Comforts, Close To Fast Food, Supermarkets And City Centre
3 1
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.
