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House holiday rentals in Chesterfield

Find and book unique houses on Airbnb

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Popular amenities for Chesterfield house rentals

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 nr Dovedale

JackRating, 5 stars2 months ago
Really good place stay, easy to find. Had a great time!
Guest favourite
Home in West Yorkshire
4.94 out of 5 average rating, 34 reviews

Shelduck, hot tub, spectacular views & spa option

ToronRating, 5 stars2 weeks ago
The property and the location was absolutely amazing , me and my friends have made some amazing memories there. The property felt luxurious and there were soo many personalised gifts for us upon arrival which were much appreciated. the host was very responsive whenever we had any questions I would absolutely recommend to anyone who wants a country escape and I know I want to go back in the future.
Superhost
Home in Hepworth

Grove Farm Cottage

ChloeRating, 5 stars1 month ago
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.
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!
Top Guest favourite
Home in Nottinghamshire
5 out of 5 average rating, 67 reviews

Stunning views - outdoor pool - cosy log burner

MarkRating, 5 stars5 days ago
Outstanding in every way. This cottage is worth more than 5* it simply cannot be beat. We have been to a lot of nice properties but Richard and Jo have made this property and their 16 acre land simply beautiful. Very nice people as well.
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.

Weekly house rentals

Guest favourite
Home in Eckington
4.88 out of 5 average rating, 41 reviews

Lovely house Eckington Sheffield

LilyRating, 5 stars2 weeks ago
Lovely clean and cosy house. Great communication
Guest favourite
Home in Derbyshire
4.97 out of 5 average rating, 111 reviews

Grade II Listed House near Chatsworth

RosemaryRating, 5 stars1 month ago
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.
Top Guest favourite
Home in Derbyshire
4.99 out of 5 average rating, 265 reviews

Chert Cottage, Great Longstone, Bakewell Peak Dist

AndrewRating, 5 stars2 weeks ago
We had a lovely, long weekend stay at Chert cottage. Great Longstone is an excellent location, with several pubs within walking distance. Beautiful scenery is on the doorstep, with places like Bakewell and Buxton a short drive away. Sarah was an excellent host - she was very responsive and we really appreciated the cake, milk and flowers on arrival. Chert cottage itself was great - very clean and equipped with everything you could possibly need - we particularly loved sitting out in the garden in the evening! Many thanks Sarah, we had a great time.
Top Guest favourite
Home in Derbyshire
5 out of 5 average rating, 17 reviews

1 Bedroom Terrace in Quiet area

ShivRating, 5 stars2 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.
Guest favourite
Home in Calver
4.87 out of 5 average rating, 228 reviews

Bridgefoot Cottage - Wild Swimming & Hot Tub

JadeRating, 5 stars2 weeks ago
Myself, my partner and our dog had a wonderful few days at Bridgefoot cottage, the photos don't do it justice is is bigger than it looks and so cosy. the garden is such a gem our dog loved it, fully enclosed and the hot tub was perfect after a long walk in the morning. Cottage itself was pristine, full of character and had everything we needed so we didn't need to contact the host for anything additional but I'm sure he would have been quick to help if we needed it. We cooked most nights but did order from the Indian (menu in the welcome book) which was a lovely change, we also walked into Calver and had some cake from the cafe there next to the Spar shop which was delicious. Great location with lots of beautiful walks nearby, one starting over the bridge and another if you turn left out of the cottage and continue down the lane you will pass through sheep fields and find yourself at Froggat woods. It truly felt like a home away from home and we would love to return in the future
Guest favourite
Home in Brassington
4.97 out of 5 average rating, 355 reviews

The Perfect Romantic Bolthole

GabrielleRating, 5 stars3 weeks ago
Such a wonderful stay at the barn. Hannah welcomed us with tea, coffee, and breakfast items making our arrival seamless and stress free. The place was immaculate and like a home from home. Finally, the cinema room was a fab addition and we were even treated with some cinema snacks left by Hannah which made the experience the best. Thank you so much, would happily stay again!
Top Guest favourite
Home in Hope
5 out of 5 average rating, 210 reviews

The Nook - an idyllic rural bolt hole...

BrianRating, 5 stars1 month ago
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.
Top 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

Superhost
Home in Mosborough
5 out of 5 average rating, 9 reviews

Detached Converted Farmhouse, Mosborough, S20

LisaRating, 5 stars10 months ago
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.
Guest favourite
Home in Derbyshire
4.98 out of 5 average rating, 49 reviews

Luxury manor house with hot tub

NiccolaRating, 5 stars5 days 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 Bolsover
4.86 out of 5 average rating, 58 reviews

The Cottage - Derbyshire

KatieRating, 5 stars1 week 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.
Guest favourite
Home in Derbyshire
4.92 out of 5 average rating, 73 reviews

Lovely 3 Bedroom house - great location

LyndaRating, 5 stars5 months ago
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 🙏
Top Guest favourite
Home in Palterton
4.97 out of 5 average rating, 35 reviews

Scrumpy's Cottage

SarahRating, 5 stars2 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
Top Guest favourite
Home in Bolsover
4.94 out of 5 average rating, 89 reviews

Bryn-Tor, The Gardener's House

AzizRating, 5 stars3 weeks 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 Clowne
4.93 out of 5 average rating, 76 reviews

Lily's Cottage

LisaRating, 5 stars2 weeks ago
Great house with everything we needed. Great value
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!

Quick stats about house rentals in Chesterfield

  • Total rentals

    60 properties

  • Nightly prices starting at

    $50 NZD 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

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  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield
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