
House vacation rentals in Chesterfield
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Top-rated house rentals in Chesterfield
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Vacation rentals for every style
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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
We really enjoyed our stay at this property. It was a perfect space for our family with plenty of space for us and our dog. The location was great - perfect for accessing the countryside and the city - with all the amenities needed for during our stay.

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.

Pet Friendly Cottage Ashbourne with Parking
Rose Cottage is a lovely place to stay and so convenient for Ashbourne and the surrounding areas. The cottage is beautifully looked after and spotlessly clean. Joanne was an exemplary host - very responsive with great communication and clear instructions. Flexibility on check out was really appreciated too.

Cosy, Exclusive Sheffield House near Peak district
We stayed at the house with 4 children and 2 adults. It was a perfect base for us as we visited friends in Sheffield and explored the Peak District. Lots of space and the boys loved the garden with a football goal. The local pub (hare and hounds) was brilliant for the range of allergies we had in our party and is walking distance from the house. Beth was very helpful and responded quickly to questions. We would definitely visit again.

Dog & Cycle friendly house with enclosed garden
We had a lovely stay in Mary’s house, she was very helpful to our queries, excellent recommendation for a dog sitter. Scenery was beautiful, we loved the house, comfy beds with exceptional good bedding, We would recommend to stay there

Barn Cottage
This was our second visit to Barn Cottage, it was just as lovely as the first! The cottage is cosy, extremely well furnished, spotlessly clean and welcoming. Jackie is a brilliant host, so much attention to detail in terms of making the cottage perfect in every way! We’d definitely recommend Barn Cottage and we’ll be visiting again!
House rentals with a pool

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
Our stay had everything and felt as if we’d struck gold with the location and amenities. The house itself is picturesque and stunning but the hot tub, games room, lawn area and sun loungers were all just added bonuses that made a family stay for all ages just perfect. We were very lucky with the weather but even in the rain we would have had just as good a stay. Thank you Nicola. What a find and what a weekend!

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

Home in Derbyshire contractors welcome
Love Kaine's place. quite spacious inside than it seems. The place was clean and welcoming. Kaine reply to my messages and even call me when I needed him. Really enjoyed my stay there 😀.

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.

Highfield House - Rural Retreat Derbyshire
We had a wonderful family stay at Penny's place during the Easter half term. It was a lovely place to come together from different corners of the UK to spend some time together and explore the surroundings.

Cosy Hillsborough terrace with breakfast hamper
The space was lovely! Very homey, and the hosts had everything set up nicely! The stairs were a bit steep - perhaps not suitable for someone with mobility issues - but very in keeping with an older home. We were very comfortable and the hosts were very responsive. Thank you for making our stay in Hillsborough so comfortable!

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
Although there were some slight issues with the hot water, completely out of their hands (these things happen) John and Juliet did everything they could to help even offering to relocate us to another property of theirs, which we really appreciated. I would definitely book with them again and would recommend. Thank you John and Juliet

10%OFF|7Nights|Leisure|Family|WiFi|Parking|6BDR
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.

Payler House>GreatLocation>CosyHome>Garden>Parking
Very nice and clean house. Claire responds quickly and has always been helpful to us, we recommend and thank you.
Quick stats about house rentals in Chesterfield
Total rentals
60 properties
Nightly prices starting at
$30 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
- Crucible Theatre
- Sundown Adventureland
- Holmfirth Vineyard
- Royal Armouries Museum
- Cavendish Golf Club
- Derwent Valley Mills
- Lincoln Castle
- Science and Industry Museum
- Shrigley Hall Golf Course
- Rufford Park Golf and Country Club
- John Rylands Library
- Bosworth Battlefield Heritage Centre
- The Nottinghamshire Golf & Country Club
- National Justice Museum
- Manchester Central Library
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