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House holiday rentals in Chesterfield

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Chesterfield

House rentals with a pool

Superhost
Home in Doncaster
4.94 out of 5 average rating, 94 reviews

Large Modern Décor 3 Bed with Driveway & Garden

Christopher JohnRating, 5 stars4 months ago
Lovely cosy house which was clean and tidy. This was our second stay at Homestead and we will be coming back.
Home in Derbyshire
4.75 out of 5 average rating, 4 reviews

Ashbourne Cottage near Dovedale

JackRating, 5 stars2 months ago
Really good place stay, easy to find. Had a great time!
Home in Derbyshire
4.71 out of 5 average rating, 7 reviews

The Farmhouse

TamaraRating, 5 stars2 weeks ago
Idyllic cottage for a countryside getaway! We stayed at the Farmhouse for 3 nights as a group of 7 adults and 2 children. We loved our stay here, can highly recommend. Clean, peaceful, comfortable beds, fast WiFi, big TV. The large kitchen was perfect for a big group with 2 ovens and dishwashers. The heated pool and game room were around the corner - technically shared with the other cottages but we were always alone when we went. 5mins drive to picturesque Bakewell. Only cons (which are not really that critical): Hosts are not responsive through Airbnb, but thankfully instructions for check in were very clear and there’s a booklet in the house with all necessary info. Kitchen could be stocked with a few additional cooking essentials, like oil and a few spices.
Guest favourite
Home in Alport
4.95 out of 5 average rating, 21 reviews

Peak District Manor: Pool + Hot Tub + Fire Pit

StephanieRating, 5 stars2 months ago
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!
Home in Bakewell
4.75 out of 5 average rating, 12 reviews

Haddon Grove Farmhouse - with pool & lots of heart

OliverRating, 5 stars5 months ago
We very much enjoyed our stay in this lovely cottage. The space is great and as an extra bonus, you get to use a heated pool and brilliant games room. We went early Jan and there was loads of snow, as well as pretty cold temperatures, but the house warmed up very quickly and we were always more than comfortable. The property is close enough to Bakewell for a short drive or taxi ride, should you want to venture into town. We're thinking about going back in the summer.
Home in Buxton
4.86 out of 5 average rating, 7 reviews

The Manor House

EiraRating, 5 stars38 months ago
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.
Home in Buxton
4.64 out of 5 average rating, 11 reviews

Badgers Wood

JackRating, 5 stars46 months ago
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.
Superhost
Home in Derbyshire
4.76 out of 5 average rating, 59 reviews

Country Cottage With Shared Swimming Pool

KellyRating, 5 stars2 months ago
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

Guest favourite
Home in Eckington
4.88 out of 5 average rating, 43 reviews

Lovely house Eckington Sheffield

StefanRating, 5 stars4 days ago
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 🤣
Guest favourite
Home in Derbyshire
4.98 out of 5 average rating, 49 reviews

Luxury manor house with hot tub

NiccolaRating, 5 stars1 week ago
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!! :)
Guest favourite
Home in Cutthorpe
5 out of 5 average rating, 22 reviews

Elegant and exclusive Manor House stay, Derbyshire

AryanRating, 5 stars1 month ago
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!
Guest favourite
Home in Bolsover
4.86 out of 5 average rating, 58 reviews

The Cottage - Derbyshire

KatieRating, 5 stars2 weeks ago
We (3 friends) had a really nice stay here. The house was very clean and well looked after and the views from the front of the house just amazing. Comfy beds, plenty of parking and the kitchen had everything we needed. Great location too for our visits to Bolsover Castle and Renishaw gardens.
Top guest favourite
Home in Derbyshire
5 out of 5 average rating, 17 reviews

1 Bedroom Terrace in Quiet area

ShivRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Bolsover
4.94 out of 5 average rating, 89 reviews

Bryn-Tor, The Gardener's House

AzizRating, 5 stars1 month ago
Had a relaxing stay near Peak district walks and close to Nottingham. A very comfortable house. Our host Judith was very helpful and kind.
Guest favourite
Home in Derbyshire
4.83 out of 5 average rating, 12 reviews

Ro's Townhouse

EmmaRating, 5 stars5 months ago
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!
Guest favourite
Home in Brimington
5 out of 5 average rating, 16 reviews

Blissful Barry’s

HarrietRating, 5 stars1 month ago
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!

Private house rentals

Top guest favourite
Home in Ashover
5 out of 5 average rating, 98 reviews

Country Cottage with great outside space & views

RichardRating, 5 stars1 week ago
Rose Cottage was excellent. The house was comfortable, beautifully furnished throughout and set in a lovely rural location. Easy to walk from the property with several village pubs and unspoilt paths making Rose Cottage an ideal base. The Garden and patio area was a great place to relax with fantastic views. Would highly recommend.
Top guest favourite
Home in Darley Dale
5 out of 5 average rating, 87 reviews

Spacious Scandinavian style hideaway with log fire

BARRYRating, 5 stars1 week ago
We've just spent a great week exploring and walking this part of the Peak District - staying at Peter's wonderful home Saunters in Darley Dale. Everything about Saunters is perfect - perfect location, quiet and peaceful with wonderful views across the countryside from the lounge and conservatory. Saunters provides a spacious and comfortable home in which to relax and unwind.
Superhost
Home in Derbyshire
4.6 out of 5 average rating, 43 reviews

Morden house in Chesterfield (5 mins to The Peaks)

NatalieRating, 5 stars7 months ago
I can't thank Simon & Sarah enough - their communication was excellent, the property was perfect and they went out of their way to accommodate us and make us feel welcome. If you have an opportunity to stay here I would 1000% recommend. If we are ever in the area again this will be my first choice. Thank you again.
Top guest favourite
Home in Palterton
4.97 out of 5 average rating, 35 reviews

Scrumpy's Cottage

SarahRating, 5 stars3 weeks ago
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
Guest favourite
Home in Nottinghamshire
4.86 out of 5 average rating, 49 reviews

Entire HOME lovely terrace cottage style house

DarrelRating, 5 stars2 weeks ago
Excellent accommodation, had everything we needed for a couple of nights stay, place was spotless with a huge warm bath! Peaceful location with plenty of parking, perfect. Jayne couldn’t have been any more helpful or responsive, a true example of how an AirBnB host should be.
Guest favourite
Home in Clowne
4.93 out of 5 average rating, 76 reviews

Lily's Cottage

LisaRating, 5 stars3 weeks ago
Great house with everything we needed. Great value
Top guest favourite
Home in Derbyshire
4.97 out of 5 average rating, 66 reviews

A luxurious home with spectacular views

MohammedRating, 5 stars3 weeks ago
A Memorable Stay with Breathtaking Views! What an amazing vacation! Our stay at this beautiful Airbnb was one of the highlights of our trip to the UK. The house was cozy, clean, and full of charm – the view… simply breathtaking! Waking every morning felt like a dream. The neighborhood was peaceful, and the location made exploring the area super easy. Our host was incredibly welcoming and made everything so smooth and stress-free. We couldn’t have asked for a better place to relax, recharge, and make memories. Highly, highly recommend – can’t wait to come back!
Guest favourite
Home in Wensley
4.96 out of 5 average rating, 68 reviews

"Ye Old Shop"

GaryRating, 5 stars1 week ago
The cottage was lovely. Paul clearly has a lot of pride in his rental. The cottage is well appointed and homely. Very well equipped small kitchen. We enjoyed the decor, quirky. No problem with parking at any time we were there, we parked right outside. If you have the weather the garden and shed are definitely a place to chill out and enjoy a drink and snacks. Great bathroom, and a good shower. Great location. If you enjoy walking it’s all down hill to the pub. Thank you Paul.

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

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield
  6. House rentals