
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!

Love Nest - an intimate hideaway
our stay at staycation cottages in bakewell was lovely. the love nest Lodge was very quaint and well equipped. the bathroom was especially layed out nicely. I enjoyed the access to the football playing area, pool area and the swimming pool. we used the bbq area once and made full use of the boot room for leaflets and information for our stay would definitely return back

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!

Stunning views - outdoor pool - cosy log burner
Absolutely perfect from booking to checking out. Richard is an incredible host with everything you need. If you have kids, this is the place. Our 6 and 4 year old loved swimming multiple times, reading the kids library of books and playing with the many toys at the house. You can’t get any better than these hosts and this house.

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.
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 🤣

Cosy terrace house in Worksop town centre
Nice and easy place to stay as a base for the weekend whilst attending a wedding in the area. First time travelling with our baby and Emma had arranged the travel cot and a fan due to the hot weather

Bridgefoot Cottage - Wild Swimming & Hot Tub
Our third trip to Bridgefoot cottage and hopefully not our last. The area is beautiful and a perfect base to explore the peaks. Would highly recommend Will’s place, the cottage and grounds are stunning and incredibly peaceful.

The Old Yoga Studio
Loved the coziness and quirkiness of the Old Yoga Studio. Minutes + walks to all the amenities including the train station, local grocery shop and pubs/restaurants. We also caught the stagecoach double decker bus to explore the local district. Kat was an exceptional host ensuring a quality stay. My husband required a physio during our stay and of the 3 suggestions we were extremely happy with our choice. Hathersage itself is an idyllic location with many walks and tours also Kat knows of a winery which is a fabulous scenic walk to and the wine is top notch!

The Nook - an idyllic rural bolt hole...
On arrival met both Naomi and Neil, Wow to the welcome, Wow to the accommodation, Wow to the views and location, Advice on how to get into Edale off the road. Sorted the electric charging, Wow we had sheep and lambs on the doorstep, Wow we had chickens running around, fresh eggs as well. Bed was so comfortable, bedroom no light pollution or noise, windows left open. Highly recommended, we will be back on many occasions.

Turners Escape
We had everything we needed for our stay. Home from home. Michelle is very friendly.

Cuckoostone Barn - simply stunning!!
I booked this stay for my mum and partner who were over the moon with their time spent here. They came back and told me they thought it was such a beautiful accommodation, with stunning surroundings. Perfect for find a little respite, peace and quiet. They were delighted with how much was provided at the accommodation, Sarah had thought of everything. They felt incredibly welcome and throughly enjoyed their stay, they’d definitely return! Thank you Sarah for providing such a lovely home for their stay!

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

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!! :)

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.

Elegant and exclusive Manor House stay, Derbyshire
We had an absolutely wonderful stay at Salli’s place. The house itself is stunning, spacious, beautifully decorated, and equipped with everything we needed for a comfortable and relaxing trip. It’s also perfectly located, with easy access to some fantastic hiking trails nearby, which we really enjoyed exploring. Salli was an excellent host—friendly, responsive, and incredibly helpful throughout our stay, making sure we had everything we needed. We would highly recommend this property to anyone looking for a peaceful getaway in a beautiful setting. Thank you, Salli, for hosting us!

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.

Bryn-Tor, The Gardener's House
Had a relaxing stay near Peak district walks and close to Nottingham. A very comfortable house. Our host Judith was very helpful and kind.

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
$38 SGD 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
- Royal Armouries Museum
- Crucible Theatre
- Holmfirth Vineyard
- The Nottinghamshire Golf & Country Club
- Cavendish Golf Club
- Shrigley Hall Golf Course
- John Rylands Library
- Rufford Park Golf and Country Club
- Derwent Valley Mills
- Manchester Central Library
- IWM North
- Bosworth Battlefield Heritage Centre