
House vacation rentals in Chesterfield
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Top-rated house rentals in Chesterfield
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Popular amenities for Chesterfield house rentals
Pet-friendly house rentals

Cosy Quiet Cottage In Pilsley
Gem of a place! Very unique house in a prime location for exploring the derbyshire dales or the peak district. I couldn’t recommend this stay more!

Lynwood - Victorian Home in the Peak District
We had a great stay at Benjamin’s house. Comfortably accommodated 7 adults and 4 children. Benjamin’s communication was excellent throughout. The house is lovely and the photos don’t do justice to the amount of space. Very well equipped. Bakewell town centre is under 5 minutes walk away. Playground and pub also very close. Located on a quiet cul de sac with enough space on the drive for three cars. Would highly recommend.

Charlesworth’s
Great stay! Ideal location for what we needed it for. Great open space for family and well equipped!

A chic retreat in the Peaks
Lovely cottage very clean. In a great place lovely walks from the doorstep. Would definitely stay again loved it.

Buxton-based family home
Lovely clean, comfortable and welcoming home. Really well equipped kitchen, super comfy beds, nice lounge. Bathroom has a lovely big bath and really good shower. Close enough to town centre and good bus and train transport links. Local shops and takeaways on the door step. Be warned walk to Buxton town steep on the way back! Overall fabulous stay in a lovely home.

Cosy, Exclusive Sheffield House near Peak district
Nice house, well fitted out and lovely location

Cosy fresh newly refurbed house
Karls house was perfect and very clean kitchen had everything you needed and more, will definitely stay back here when in the area for competitions

Dog & Cycle friendly house with enclosed garden
place was lovely and well kept. there was plenty of locked storage for bikes if that's your thing, and a stair gate if you're taking animals. we had two 6 year olds and they lived there place too. kitchen diner is well set of four a family of 4 to have some quality table time.
House rentals with a pool

Ashbourne Cottage near Dovedale
Lovely stay, very responsive to any problems and very professional.

The Farmhouse
We had a wonderful stay at the Farmhouse - the postcode took us to the farm, but the cottages were close by and easy to find. The kitchen was very well stocked with crockery and there was plenty of space for 10. The kids loved the swimming pool and football field. Highly recommended.

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!

Haddon Grove Farmhouse - with pool & lots of heart
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.

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.

Charming Cottage with Indoor Swimming Pool
great cottage in a fantastic location with Carsington Water in walking distance and a lovely country pub too! Cottage had everything we could have asked for and our host was really helpful when we needed them. Highly recommend :)

The Round House - family house with indoor pool
This was a last minute booking and we got really lucky with this gem. It was the most beautiful setting and the house was charming and very spacious and perfect for the surrounding views which are just stunning. The house had all that you would need and is very comfortable and cosy. The welcome folder was informative nd highlighted local amenities and places of interest. The location is accessible and there are so many local shops and big supermarkets on your doorstep. It makes for an easy and stress free break. I would highly recommend staying here and the hosts accessibility and prompt responses was what made this experience perfect.
Weekly house rentals

5-Bed Home Near Sheffield for Festive Stays
We had a group of friends needing a place to stay for a nearby wedding. We came across this place. It was a 10 min walk to where we needed to be. Perfect. The accommodation was spot on, clean, tidy, and every thing you would expect from a large house. Would recommend and so would all the gang who stayed.

Home in Derbyshire contractors welcome
Adorable home perfect for our overnight stay. Extremely clean & tidy. Both bedrooms were large & nicely furnished. So lovely and quiet at night, very restful sleep. Kaine was a perfect host and the property was easy to find and get into. Nice & decent size Co-op on the main road B6016, about 5 minutes walk. Also, a few takeaways, pubs around there and on Somercotes Road. We had a relaxing, very comfortable stay, thank you Kaine

Cosy terrace house in Worksop town centre
Emma’s was a lovely place to stay it felt very cared for and as guests we felt very cared for. Emma had really thought of everything. We were lucky with the sunny weather and enjoyed having lunch in the garden. It was very quiet and peaceful. Emma was very kind and helpful.

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 🙏

#WiF,FreeParking,Discounts,Contractors,SmartTV#
Had a relaxing stay at Tom’s. He accommodated us right away and made it quite easy to check-in. Also helped out with what we required. The place is as described. Quite clean and fresh. It had everything we needed. Would like to come back again

3 Bed Perfect For Contractors! Long term discount!
Good size, clean ,good layout , only annoyance was that it has has off street parking but unable to access but parking on street not a problem

Wickersley House: Contractors & families, parking
John and Juliet's house is the cleanest we have ever stayed in! The bedsheets were also really soft and comfortable. We were visiting family in the surrounding villages, visiting at the local hospital and travelling to the office in Leeds so the location was ideal. We didn't try to walk anywhere but it was only a few minutes to drive to the supermarket and to the shops and cafes in Wickersley. It is a busy street with lots of cars parked but we never had an issue with access to the drive even with 2 hire cars. John and Juliet must have had guests who have disrespected their house before as there were signs on the lounge door, on the landing and a list of the rules printed out in the lounge. It is a shame they have had to do that as it just takes away some of the homely feel. As with every property we stay in, more coat hangers would be helpful 🤗

Weekly Deal | Save10% | WiFi | Parking | Sleeps 12
Roberts' place was ideal for our business trip – incredibly spacious with super comfortable beds. The location was excellent, making it convenient for everything we needed. Communication was seamless throughout our stay. Highly recommend, and we’ll definitely return on our next visit to the area.
Quick stats about house rentals in Chesterfield
Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ110 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
- Etihad Stadium
- Chatsworth House
- Drayton Manor Theme Park
- Harewood House
- IWM North
- Tatton Park
- Mam Tor
- Sundown Adventureland
- Crucible Theatre
- Lincoln Castle
- Royal Armouries Museum
- Holmfirth Vineyard
- Cavendish Golf Club
- Derwent Valley Mills
- Shrigley Hall Golf Course
- Science and Industry Museum
- Rufford Park Golf and Country Club
- John Rylands Library
- The Nottinghamshire Golf & Country Club
- National Justice Museum
- Bosworth Battlefield Heritage Centre
- Manchester Central Library