Chesterfield holiday rentals: compare the best deals
9.4 7 reviews
Chesterfield
06/27 – 07/04
HK$2404/nighttotal: HK$16828 (7 )
Payler 4 Bedroom House Stylish With 7 Beds Parking Near M1
4 8
house , Sheffield
This charming house is situated just 5 kilometres from FlyDSA Arena and within easy reach of Chatsworth House (27 kilometres) and Eco-Power Stadium (31 kilometres), offering a convenient base for exploring Sheffield and the surrounding area. The property is ideal for families or groups, with 4 bedrooms, a living room, and a fully equipped kitchen, offering 120 square metres of space for up to 10 guests. Enjoy a peaceful stay with a private entrance and soundproofing, and relax in the garden with patio views. The house has free Wi-Fi, a large parking space, and comfortable amenities including towels and bed linen.
9.2 4 reviews
Chesterfield
08/28 – 09/01
HK$1008/nighttotal: HK$4032 (4 )
The Old Hayloft-uk39431
1 2
house , Dronfield
The Old Hayloft is a one-bedroom house in Dronfield, Derbyshire, conveniently located 13.5 km from Sheffield’s Utilita Arena and 17.7 km from Chatsworth House. This self-catering property sleeps three guests and features free Wi-Fi, private parking, a dishwasher, and a private entrance.
8.3 267 reviews
Chesterfield
07/07 – 07/08
HK$681/nightfor 1 night
All Inn Apartments
1 1
apartment , Staveley
All Inn Apartments is located in Staveley, just 19 kilometres from the FlyDSA Arena and 24 kilometres from Clumber Park, offering easy access to both city attractions and countryside escapes. This apartment has received very good ratings for its location, cleanliness, and overall experience. The apartment has one bedroom and one bathroom, covering a spacious 900 square metres. You'll find a fully equipped kitchen with a fridge and microwave, a washing machine, free Wi-Fi, a relaxing garden, and free private parking, making it ideal for a comfortable and convenient stay.
9.8 33 reviews
Chesterfield
06/26 – 06/28
HK$1523/nighttotal: HK$3046 (2 )
Blissful Barry’s
1 4
apartment , Brimington
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.
9.8 38 reviews
Chesterfield
08/08 – 08/09
HK$2027/nightfor 1 night
Home Away From Home
1 2
apartment , Derbyshire
This pet-friendly Derbyshire apartment is situated on the edge of the Peak District National Park, within easy driving distance (approximately 20-30km) of Chesterfield, Sheffield, Bakewell, and Matlock. The two-bedroom dwelling offers comfortable accommodation for up to four guests, boasting a kitchen with fridge, freezer, and microwave, a secure garden, off-road parking, and excellent guest ratings; explore the Peak District's attractions from this convenient base.
9.1 55 reviews
Chesterfield
08/08 – 08/09
HK$1575/nightfor 1 night
Ringinglow Cottage
1 2
house , Sheffield
Toy Cottage Sheffield is located on a quiet street in Sheffield, just 8.5 kilometres from Sheffield Train Station and 22.5 kilometres from Haddon Hall. The property has received excellent ratings for its location, cleanliness, and overall experience. The cottage is a one-bedroom property with one bathroom, covering 23 square metres and accommodating up to two guests. It offers a fully equipped kitchen with a dishwasher, oven, and microwave, a terrace with quiet street views, and free private parking, making it perfect for a comfortable and convenient stay in Sheffield.
9.9 30 reviews
Chesterfield
08/28 – 09/01
HK$1398/nighttotal: HK$5592 (4 )
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.
9.7 3 reviews
Chesterfield
08/01 – 09/30
HK$1441/nighttotal: HK$86460 (60 )
Blue Lagoon Retreat Escape Free Parking 14ppl
3 2
house , Sheffield
Blue Lagoon Retreat Escape is a detached house located in Sheffield, 6.28 kilometres from Utilita Arena Sheffield and 22.53 kilometres from Chatsworth House. This detached house offers accommodation for up to 14 guests with 3 bedrooms, 1 bathroom, a microwave oven, a garden, and on-site parking, covering a floor area of 78 square meters.
9.9 325 reviews
Chesterfield
10/18 – 10/26
HK$1028/nighttotal: HK$8224 (8 )
Chatsworth Cottage
2 5
apartment , Chesterfield
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.
Chesterfield
08/01 – 09/30
HK$483/nighttotal: HK$28980 (60 )
Bright & Contemporary Studio In Sheffield W Wifi
1 2
studio , Sheffield
This contemporary studio apartment in Sheffield is located in a residential area, offering convenient access to local attractions with Utilita Arena Sheffield 5.95 kilometres away. This 28 square metre studio, accommodating up to three guests, features a well-equipped kitchen with a fridge and microwave, and provides complimentary WiFi for your convenience.
10 182 reviews
Chesterfield
07/07 – 07/08
HK$809/nightfor 1 night
Chesterfield -Peak District-chatsworth-ev Charger
1 1
apartment , Derbyshire
This ground-floor studio apartment is situated on a quiet avenue in Chesterfield, Derbyshire, offering easy access to Chatsworth Road's amenities and within a short driving distance (approximately 20-30km depending on the specific destination) of the Peak District National Park, Chatsworth House, Buxton, Bakewell, and Matlock. The self-contained unit, sleeping up to two guests, features a kitchenette with a fridge-freezer and microwave, a private bathroom, and a comfortable double bed; nearby attractions include the Hipper Valley trail ideal for cycling.
9.7 3 reviews
Chesterfield
08/21 – 08/23
HK$919/nighttotal: HK$1838 (2 )
Clay Cross Small Two Bedrooms House
1 2
house , Clay Cross
This two-bedroom cottage in Clay Cross is located 21 kilometres from Chatsworth House, 30 kilometres from Clumber Park, and 32 kilometres from Utilita Arena Sheffield. This property offers free WiFi, a fully equipped kitchen, and a flat-screen TV, accommodating up to five guests with a check-out time of 10:00 AM.
Best family friendly Chesterfield holiday rentals
Among the 134 accommodations in Chesterfield, here are the 4 best family friendly rentals
9.6 103 reviews
Chesterfield
07/07 – 07/08
HK$16897/nightfor 1 night
Manor House
5 1
house , Chesterfield
The Manor House is located in Chesterfield, a short drive from Chatsworth House (21 km), FlyDSA Arena (26 km), Clumber Park (27 km), and Sherwood Forest (34 km), offering easy access to popular attractions. The house has received excellent user ratings for its cleanliness, location, and overall experience. The property is a spacious five-bedroom home with a floor area of 160 square metres, accommodating up to 10 guests. The Manor House includes a fully equipped kitchen, a swimming pool, a Jacuzzi, a terrace, a garden, and a fitness centre, providing everything needed for a relaxing and enjoyable stay.
9.5 11 reviews
Chesterfield
10/18 – 10/26
HK$11644/nighttotal: HK$93152 (8 )
215 M² House ∙ 7 Bedrooms ∙ 20 Guests
7 5
house
This spacious eco-friendly house is located in Chesterfield, just a five-minute walk from Chesterfield Station and within easy reach of the town centre, shops, and restaurants. It has excellent user ratings and is perfect for families and large groups. This seven-bedroom property has a floor area of 215 square metres and can comfortably accommodate up to 20 guests. The house has a fully equipped kitchen, two living rooms, a games room with a pool table, table tennis, and a PlayStation, a hot tub, a sauna, a barbecue area, and a garden with views of the Derbyshire countryside.
10 1 review
Chesterfield
06/27 – 07/04
HK$1720/nighttotal: HK$12040 (7 )
Perfect Booking 4 Bed Home In Sheffield
4 8
house , Elland
This 4-bedroom property in Sheffield is located 6.27 kilometres from Utilita Arena Sheffield, 22.53 kilometres from Chatsworth House, and 32.19 kilometres from Cusworth Hall, making it ideal for contractors and long stays. This detached house for 16 guests offers a fully equipped kitchen with a dishwasher and oven, a Jacuzzi, a garden, and free WiFi, with a patio for outdoor space and a check-out time of 11:00 AM.
9.4 284 reviews
Chesterfield
06/26 – 06/28
HK$2855/nighttotal: HK$5710 (2 )
Refurbished Plush Property Great Transport Links
3 4
house , Sheffield
This property is located in Sheffield, just 6 kilometres from the FlyDSA Arena, offering easy access to major attractions like Chatsworth House (24 kilometres) and Cusworth Hall (39 kilometres). The property has received excellent ratings for its location, cleanliness, and overall user experience. The house has 3 bedrooms and 1 bathroom, comfortably accommodating up to 10 guests. It features a fully equipped kitchen, a private garden with a patio, free parking, and free Wi-Fi, making it an ideal choice for families or groups visiting Sheffield.
Best Chesterfield holiday rentals with parking
9.3 11 reviews
Chesterfield
10/18 – 10/26
HK$1245/nighttotal: HK$9960 (8 )
Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & The Peak District
2 5
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.
Chesterfield
07/04 – 07/05
HK$4102/nightfor 1 night
The Old Chapel, Handley
2 2
apartment , Chesterfield
This unique chapel conversion is located in Handley, Derbyshire, 3.2 kilometres from Clay Cross and within easy reach of Matlock and Chesterfield's attractions, including the Chesterfield Museum & Art Gallery. This two-bedroom flat accommodates up to four guests and offers off-road parking for two cars, a lawned garden area with seating, and an electric woodburner for a cosy atmosphere, with the Derbyshire Dales providing a picturesque setting for outdoor pursuits.
Chesterfield
09/26 – 09/27
HK$8293/nightfor 1 night
Swallows Barn
1 2
cottage , Chesterfield
This Chesterfield cottage, situated within 5km of Queen's Park, Mecca Bingo, St Mary and All Saints' Church, and 4.7km from Chesterfield Market, offers self-catering accommodation with free on-site parking and Wi-Fi in communal areas. The property features two bathrooms, a fully equipped kitchen including a dishwasher, and a private garden; it's ideal for sporty travellers given its proximity to recreational facilities.
10 4 reviews
Chesterfield
09/26 – 09/27
HK$3222/nightfor 1 night
2 Bedroom Accommodation In Holymoorside
2 2
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.
Frequently asked questions about holiday rentals in Chesterfield
What should a first-time visitor not miss in Chesterfield?
You definitely want to see the Crooked Spire, it's Chesterfield's most famous landmark. A trip to the Chesterfield Museum & Art Gallery is a must too, it's a great way to learn about the history of the town. And for a bit of green space, the Queen's Park is a lovely spot to relax.
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 a good bet if you want to be close to the action. If you're looking for something a bit quieter, try the area around Queen's Park, it's lovely and green.
What are the most popular Airbnbs in Chesterfield?
What are the top family-friendly attractions in Chesterfield?
Chesterfield's a great place for families. You've got the Chesterfield Canal, which you can explore by boat, the Chesterfield Museum & Art Gallery has lots of interactive exhibits for kids, and the Queen's Park has a playground and lots of open space to run around in.
What are the best vacation rentals with a pool in Chesterfield?
When is the best time to book a vacation rental in Chesterfield?
The best time to book a vacation rental in Chesterfield is usually during the shoulder seasons, like spring and autumn, when the weather's nice and the prices are a bit lower. You might want to book a bit earlier if you're planning to visit during the summer, especially if you're coming for a festival or event.
What are the best rentals for families and kids in Chesterfield?
What events or festivals should visitors check out in and around Chesterfield?
The Chesterfield Food and Drink Festival is a big one, it's held in the town centre and has lots of stalls selling local produce. And there's the Chesterfield Beer Festival, which takes place at the Winding Wheel.
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 a great way to see the town. The Chesterfield Museum & Art Gallery has free entry, and the Queen's Park is a beautiful spot to relax and enjoy the sunshine.
What are the best restaurants with local dishes in Chesterfield?
The Old House is a popular choice, they serve classic British dishes and have a great atmosphere. For something a bit more modern, try The Tap, they do delicious burgers and have a good selection of craft beers.
What are the best walking or cycling routes in Chesterfield?
The Chesterfield Canal towpath is a great place for a walk or cycle, it stretches for miles and takes you past some lovely countryside. You can also find some good walking trails in the Queen's Park.
Are there pet-friendly attractions in Chesterfield?
The Queen's Park is a great place to take your dog for a walk, and many pubs in the town centre are dog-friendly.
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 one with a kitchen so you can cook your own meals. They're also a good option if you're travelling with a family or a group of friends.
What are the top sports attractions and facilities in Chesterfield?
The Proact Stadium is home to Chesterfield FC, a popular football club, and there's also a bowling alley and a leisure centre with a swimming pool.
Destinations nearby
Best Chesterfield holiday rentals with a balcony
Chesterfield
06/27 – 07/04
HK$3553/nighttotal: HK$24871 (7 )
Apartment ∙ 5 Bedrooms ∙ 12 Guests
5 8
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.
9.5 2 reviews
Chesterfield
08/01 – 09/30
HK$1719/nighttotal: HK$103140 (60 )
Southdown House Doe Lea By Smart Corporate Stays
4 2
house , Ault Hucknall
Southdown House, a four-bedroom property in Ault Hucknall, Nottinghamshire, offers convenient access to attractions such as Clumber Park (24km), Chatsworth House (29km), Sherwood Forest (30km), Nottingham Castle (35km), and the Utilita Arena Sheffield (35km). This 132 square metre self-catering house boasts a spacious layout including a living room, fully equipped kitchen, two bathrooms, free Wi-Fi, private parking, and a terrace; accommodating up to 39 guests.
8.6 6 reviews
Chesterfield
08/21 – 08/23
HK$1307/nighttotal: HK$2614 (2 )
Matlock Town Centre Flat Near Transport Links
1 2
apartment , Matlock
This Matlock town centre flat offers convenient access to transport links and is situated 12.4 km from Chatsworth House. The 34-square-metre self-catering apartment features one bedroom, one bathroom, a balcony, and sleeps up to three guests, including children accompanied by a responsible adult.
9.1 780 reviews
Chesterfield
10/18 – 10/26
HK$2245/nighttotal: HK$17960 (8 )
Barlow Country Club - Mill Farm Cottages
3 5
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.
Best Chesterfield holiday rentals with air conditioning
10 1 review
Chesterfield
08/21 – 08/23
HK$2111/nighttotal: HK$4222 (2 )
Spacious 4 Bed Home For Families & Contractors.
4 2
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.
9.8 14 reviews
Chesterfield
06/26 – 06/28
HK$2754/nighttotal: HK$5508 (2 )
Number 26 Van Dyk Village
3 4
house , Chesterfield
This three-bedroom house, situated in Van Dyk Village, Chesterfield, is conveniently located 19km from Sherwood Forest, 26km from the FlyDSA Arena, and 32km from Clumber Park. The 42 square metre property offers free Wi-Fi, private parking, a patio, and sleeps up to nine guests, boasting a fully equipped kitchen, living room and a peaceful garden setting.
Chesterfield
06/25 – 07/16
HK$2935/nighttotal: HK$61635 (21 )
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.
9.0 8 reviews
Chesterfield
08/21 – 08/23
HK$11748/nighttotal: HK$23496 (2 )
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.
