
House holiday rentals in Chesterfield
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Top-rated house rentals in Chesterfield
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Popular amenities for house rentals in Chesterfield
House rentals with a pool

Large Modern Décor 3 Bed with Driveway & Garden
Lovely cosy house which was clean and tidy. This was our second stay at Homestead and we will be coming back.

Ashbourne Cottage near Dovedale
Really good place stay, easy to find. Had a great time!

Grove Farm Cottage
Lovely stay, the farm was beautiful and the animal feeding was the highlight of our childrens’ stay. Pool was great, super clean everywhere, and they provided maps of local walks which we utilised too. Couldn’t have asked for much more.

Peak District Manor: Pool + Hot Tub + Fire Pit
The house was absolutely incredible and excellent value for money. It was in stunning surroundings, the hot tub was amazing and the exclusive booking system for use of the pool was a lovely addition. The house was spotless and full of character and the private garden was also wonderful. The beds were really comfortable and there was just the right balance of charm, space and comfort. We definitely struck gold when booking this gem. Thanks so much for all of your support in making this a trip to remember!

The Manor House
What a wonderful stay at Manor Farm. The house was beautiful, well maintained, extremely spacious and very comfortable. The surrounding countryside was stunning, with great food being served in nearby pubs and plenty of places to visit. Great space for youngsters too, with the wildlife - baby rabbits, sheep and birds and of course the swimming pool and games room, all of which they loved. Thanks to the hosts for their welcome and hospitable atmosphere.

Badgers Wood
Great value for money. Can't stress enough how friendly and reliable the staff were. We had a lovely week stay, the house was clean, the beds were comfy and the scenery was perfect. We were informed of the booking system for the swimming pool and games room, so you could have the room to yourself which was great. The pool was clean, the games room was kept tidy and the house surroundings were really lovely to walk around. You can tell the grounds were well maintained and kept in good shape as the workers never stopped, but were always so friendly. This property is perfect for bike riders, walkers and pub crawlers. You couldn't get bored.

Buttercup Down - with heated pool & games room
Fabulous place - we stayed for a week - with 2 teenagers, a preteen and our dog - great field opposite to run the dog morning and evening. Plenty of beautiful walks straight from the front door. 45 minutes to nearest place to eat out. Facilities were great - lots of swimming and football played by our kids. Thanks for a great stay.

Country Cottage With Shared Swimming Pool
Lovely cottage in beautiful surroundings, very clean and tidy. My children loved the pool and games room. Easy to get to all the main attractions will be coming back soon. Thank you for a great stay!
Weekly house rentals

Lovely house Eckington Sheffield
Great initial communication with Steven and throughout. he proactively got in touch shortly before the stay and we easily arranged the check-in time as he was going to meet me at the property. I was closer to the end of window I said I'd be, but he was ready and waiting at the property. Had a nice chat about my journey and plans for the weekend, learning a little of Stevens history also, before a quick house tour. The house is easily accessible and I was lucky with the parking, finding a roadside spot directly outside, did appear to be parking up and down the street also. The house was clean and tidy. Very well stocked kitchen though I didn't use any of the tea/coffee/jams though I didn't use any of them. Overall, felt like a comfortable stay, home from home. Only downside was the heat and lack of a fan though in this British weather a fan would likely just push the warm air around the house 🤣

Grade II Listed House near Chatsworth
Vernon House is a lovely place to stay. It worked well for a group of friends coming together for a reunion. The kitchen is well equipped for cooking meals for 10 people. The house is well laid out and tastefully decorated. We enjoyed a walk to Chatsworth House along a well marked footpath. Noise from the A6 was most noticeable on Sunday when we sat in the garden. In the house the traffic could not be heard. We were very happy with the house we had chosen for our gathering.

Beautiful home with Stunning views and log fire.
We stayed here for a wedding and everything was spot on. The location is amazing, only about a 5 minute walk to everything we needed. I jokingly said it smelt like fresh bed when we opened the door - but that's exactly what it was as Paul had left us a note saying the fresh bread he'd baked us would be ready at 6! The fridge and freezer were also left full of supplies for us. Jill and Paul responded to our messages very quickly and helpfully throughout the stay and we would absolutely recommend staying here.

The Old Yoga Studio
Had a wonderful stay at The Yoga Studio. The place was clean, well-managed and easily accessible . The hospitality was outstanding, the host Kat even came in person to make sure everything was okay. Truly appreciated.

"The Barn” at Stoop Farm
Richard's place has a lovely blend of feeling like you're in the middle of nowhere yet being only a 15 drive into thriving Buxton. It was warm, comfortable and a great size for a family get-together, with some amazing walks literally on your doorstep. We can all genuinely say we thoroughly enjoyed our stay!

The Perfect Romantic Bolthole
Hannah's place was one of my favourite Airbnbs of all time - the space, decor, amenities and all the little touches were just fantastic. The location is perfect and access to everything the Peak District has to offer could not be better. Offstreet parking was super convenient. The place was spotless clean. Hannah was a lovely, kind and very helpful host. Thanks for a great stay!

The Old Timber Store - tiny home in a village
The Old Timber Store was everything and more, a gorgeous little gem nestled in the Derbyshire Hills. The property itself was tastefully decorated with beautiful furnishings (I’ve definitely taken some inspiration for my own home!), and the location was lovely! The amenities in the village were wonderful and the property was so close to Haddon Hall and Chatsworth - was really easy to nip back and forth with our 6 month old daughter. A wonderful stay with lots of gorgeous walks, if you’re thinking about booking this place - do it!

Commuters Getaway Chesterfield
we have just spent 5 days there would recommend it.Dan was very helpful .The house is very central for exploring the Peak District and is a nice walk into Chesterfield about 20 minutes, plenty of pubs to choose for meals .
Private house rentals

Detached Converted Farmhouse, Mosborough, S20
A beautiful house, and a great host. The property was just like the description and photos. Great for us as we have family close by. Dean was brilliant at keeping in touch and came back whenever I messaged him. Will certainly book again. Thank you for an amazing stay.

Luxury manor house with hot tub
We loved our stay at Gill and Steve’s. It’s one of the nicest we have ever stayed in. My husband and I plus 8 of our friends stayed for two nights. We had so much fun!!! The outside space is perfect for dinners and drinks. The house is huge and has everything we needed. Gill and Steve are amazing hosts. Such good people and were so responsive and helped us to make a lovely weekend for our friends. Enough parking for all 5 couples to drive!! Will be back!! :)

1 Bedroom Terrace in Quiet area
I stayed at Sams place for almost two months and it was one of the best decisions ever. The house is very well done and in a very nice and safe location. It is close to bus stops and the royal hospital. Sam replied almost immediately if I had any questions or doubts. The house is spacious and with a very nice backyard as well. I'm glad I could this place a home for 2 months. I would highly recommend Sams place for anyone looking to stay in Chesterfield for short/long term.

Lovely 3 Bedroom house - great location
We used this lovely home while waiting for the purchase of our new home to complete, we wanted somewhere in Chesterfield that was going to feel like a home and be comfortable while I’m undergoing chemo, Winston’s home ticked every box and our 2 dogs and 2 house cats definitely approved, the garden is secure and safe, parking outside was perfect, we couldn’t have picked a better property, even suppling a Christmas tree and decorations made it that much more special, thank you 🙏

Scrumpy's Cottage
We spent a lovely few days at Scrumpy’s Cottage - it’s beautifully decorated with lots of quirky but tasteful touches. The welcome basket of goodies went down well too. Jo was quick to answer any pre arrival questions and she and Adam were perfect hosts when we visited their micro pub next door - really friendly as were all the locals. Super little home from home. Thanks so much

Lily's Cottage
Great house with everything we needed. Great value

Ro's Townhouse
Thank you so much for a lovely stay Kirsty! Exactly what we were looking for. Stayed for 2 nights to try and get some climbing in around Stanage and Matlock, was a great location to drive to the crag. Comfortable and roomy and amazing to be dog friendly. Perfect!

Blissful Barry’s
A comfortable and well appointed Airbnb in a lovely peaceful area. Host was always quick to respond to any questions and the whole process was easy and efficient. Would definitely recommend to anyone looking to stay near Chesterfield but in a more relaxed area!
Quick stats about house rentals in Chesterfield
Total rentals
60 properties
Nightly prices starting at
₹2,596 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Peak District national park
- Alton Towers
- Peak District
- The Quays
- Etihad Stadium
- Chatsworth House
- Drayton Manor Theme Park
- Tatton Park
- Lincoln Castle
- Harewood House
- Sundown Adventureland
- Mam Tor
- IWM North
- Crucible Theatre
- Royal Armouries Museum
- Holmfirth Vineyard
- Cavendish Golf Club
- Shrigley Hall Golf Course
- The Nottinghamshire Golf & Country Club
- John Rylands Library
- Rufford Park Golf and Country Club
- Derwent Valley Mills
- Manchester Central Library
- Bosworth Battlefield Heritage Centre