Family-friendly holiday rentals in Chesterfield

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Popular amenities for Chesterfield family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Cottage in High Peak
4.88 out of 5 average rating, 572 reviews

HOT TUB Luxury Converted Barn

JaneRating, 5 stars1 day ago
The house was lovely, great location and within easy reach to places of interest. Kitchen outstanding layout and homely. Beds were very comfortable and hot tub great after a long day on the hills! However, the bedroom upstairs has a step that leads to the stairs and if you lose your footing will cause a serious accident as railings are not secured as they should be, and wobbles as you hold on going up and down stairs. No en-suite upstairs so if you want the loo during night, and miss that step it would be good night sienna! The sofa looks new but very very uncomfortable and I found the floor better to park my bum. There are some chips in a couple of the cups and a few wear/tear marks on the bar stools. The host responded in a timely manner to a couple of questions which I had about WiFi code and my stay was home from home, we enjoyed our 4 nights in the Peaks. Thanks Scott.
Guest favourite
Barn in Green Moor
5 out of 5 average rating, 30 reviews

The Stables 1 bedroom with Private Hot Tub

DavidRating, 5 stars2 weeks ago
The private hot tub was so nice and the views amazing. The accommodation was modern and clean. The big bath tub was great for relaxing in. Yummy Yorkshire does a nice breakfast not too far away, and there’s a Lidl right near if you want to do your own cooking.
Superhost
Home in Ashbourne
4.96 out of 5 average rating, 82 reviews

The Old Wash House Self Catering

EliseRating, 5 stars3 months ago
So enjoyed our stay at the Old Wash House. Everything was perfect from location to cottage & hosts couldnt have been any more accommodating. So many special touches from the freshly baked warm bread hanging on our door in the morning to the fire lit for our arrival. We loved it all & def hope to return ❤️ 😍
Superhost
Cottage in Carsington
4.8 out of 5 average rating, 224 reviews

Luxury SC Cottage Lake views 6-8 Guests

DanRating, 5 stars2 weeks ago
Very cosy, stylish and relaxing place to stay - lovely views, great pub 5 mins walk away and lots to do in the local area. Highly recommended!
Guest favourite
Home in Oakerthorpe
4.89 out of 5 average rating, 90 reviews

The Old Milking Parlour with private hot tub

SueRating, 5 stars3 weeks ago
Great stay, the kids loved helping farmer Vic in particular!
Superhost
Cottage in Matlock
4.88 out of 5 average rating, 428 reviews

Owslow Cottage with hot tub & Alpaca Walking

JohnRating, 5 stars2 weeks ago
Great location and a very helpful host.
Guest favourite
Farm stay in Loversall
4.93 out of 5 average rating, 81 reviews

Entire home - Garden Cottage, Loversall

JaneRating, 5 stars3 weeks ago
Beautiful house in stunning surroundings. very quiet and peaceful. We walked to Annabelles Cafe which was about a 25/30minute rural walk and very much worth it when we got there, great food and drinks in the sunshine were had! The house had everything we needed and was very clean. We paid a little extra for a later checkout and were glad we did so that we could enjoy breakfast once more in this gorgeous place. The hot tub was a great added extra and we made great use of it while we were there.
Top Guest favourite
Barn in Ford, Leek
4.93 out of 5 average rating, 190 reviews

5* Stunning Secluded Luxurious Converted Barn

KathleenRating, 5 stars3 weeks ago
A wonderful set up at Ford Whetley. Idea for walking in the Peak District and great pubs with food within easy reach (recommend pubs at Onecote and the Black Lion at Butterton.) Louise was a great help in advance of our arrival and communicated really effectively. A beautiful area of the country. Would recommend this cottage to anyone - you won't be disappointed. Thanks again Louise!

Family- and pet-friendly home rentals

Guest favourite
Home in Derbyshire
4.91 out of 5 average rating, 312 reviews

Buxton-based family home

MoraigRating, 5 stars1 month ago
Great spot, perfect for exploring Buxton and the surrounding area. Lovely house and although the bedrooms are a tad small we only needed them to sleep in and that was more than made up for in the excellent kitchen, garden and living areas. Perfect for a girlie getaway! Grace was a great host, very responsive to messages. Some basic kitchen bits and bobs (including mini milk bottle!) were a nice touch. Would stay again
Top Guest favourite
Townhouse in Eastwood
4.95 out of 5 average rating, 153 reviews

Victorian miners cottage - In small town centre

Alan & WanlinRating, 5 stars4 weeks ago
We stayed at Maxine’s place for six days due to work, and it truly felt like home. Our dog Domi also loved it and felt completely safe and at ease. The house absolutely exceeded our expectations, it’s so well-stocked that we didn’t even need to go grocery for the first few days! There are plenty of restaurants, supermarkets, and parks within walking distance, and parking was super convenient. Maxine also recommended an amazing Thai restaurant — unfortunately, we couldn’t get a table because we didn’t book in advance, but that just gives us another reason to come back! Highly recommend to everyone :)
Guest favourite
Cottage in Bakewell
4.89 out of 5 average rating, 299 reviews

Chatsworth Cottage, Little Longstone

JohnRating, 5 stars1 month ago
Sam and Annie's cottage was a lovely location to spend 8 days as a family of three (including with a 9 month old baby). It included a large and very comfortable bed, a cot in a separate room for our baby, and everything needed in the kitchen to be able to make a meal. They were very helpful at making sure we had everything we needed for the baby (e.g. high-chair, baby bath, etc) and were very responsive to any questions that came up during our stay. The cottage is in a lovely spot, with walks right on its doorstep, and Monsal Head a short 5 minute walk away. The local pub is also excellent (ensure to make a reservation). We would not hesitate to stay here again.
Guest favourite
Cottage in Derbyshire
4.9 out of 5 average rating, 199 reviews

Shippon Cottage, Castleton, Peak District

MarkRating, 5 stars6 days ago
We chose this accommodation due to its location near to the Peaks. The cottage was really peaceful and in a cracking location. Maeve greeted us on our arrival and explained all we needed and she even sorted some extra heating for us. Will be staying again soon
Guest favourite
Cottage in Whitwell
4.91 out of 5 average rating, 127 reviews

Whitwell character house 20 mins to Peak District

SalmanRating, 5 stars2 weeks ago
we enjoy alot living in the house. very comfy beds , lots of space , house was nice and tidy, will love to come back in further if needed. definitely recommend. 5 stars all the way ✨️ 😍 💛
Top Guest favourite
Home in Boothstown
4.94 out of 5 average rating, 112 reviews

62 Manchester Road

MaryamRating, 5 stars2 months ago
Colin's place was lovely, we felt right at home! Loved all the quirky collections around the house. Everything in the house was clearly thought out especially the binder! It had everything from house manuals to places to eat and explore around Thurlstone/Penistone. The location was an ideal base for nature walks/hikes as it's only a few steps from trans-penine trail. It was lovely to meet Colin on our way out too!
Superhost
Home in Derbyshire
4.81 out of 5 average rating, 363 reviews

The Garden Cottage

LauraRating, 5 stars2 weeks ago
Absolutely beautiful cottage and was made to feel at home. Perfect location for a relaxing few days, and the dog loved the secure garden. Cottage was homely inside and had all the necessary amenities, the milk and brownies were a lovely added touch. Will definitely return, cannot fault it. Sarah was also lovely and very friendly and helpful.
Top Guest favourite
Cottage in Tideswell
4.92 out of 5 average rating, 345 reviews

Lawrence cottage, spacious and central location

AmandaRating, 5 stars1 week ago
Lovely place to stay - very welcoming and comfortable with everything you need

Family-friendly home rentals with a pool

Guest favourite
Home in Winster
4.86 out of 5 average rating, 51 reviews

Charming 6-Bedroom Winster Village, Peak District

KayaRating, 5 stars3 weeks ago
We had a lovely time staying at the Old Angel with a large group of women. The sheer number of bathrooms was super handy with the large group number, and the living and dining spaces were super functional for a group of our size. There is a one half freezer and a large fridge, which Nicola had left some treats in which was a lovely touch. Bedrooms were well organised and very clean, with towels provided. There’s a village shop right next door, and a pub 20 meters away which was glorious in the May sunshine. Nicola and her team were very helpful in response to any questions/feedback we we had - overall we had a lovely stay and I would recommend this place to others!
Top Guest favourite
Cottage in Fenny Bentley
4.95 out of 5 average rating, 347 reviews

Luxury Peak District Home - 2 miles from Ashbourne

CeliaRating, 5 stars1 week ago
Beautiful cottage set in wonderful grounds with a playhouse for the little ones. The pool was great too. Such a great place to stay, and under 10 minutes from Ashbourne. Around 30 mins to kid friendly hiking/walking in the Dales. Highly recommend.
Home in Bakewell
4.73 out of 5 average rating, 11 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.
Superhost
Cottage in Hope
4.7 out of 5 average rating, 46 reviews

Birch Cottage

PhilipRating, 5 stars2 months ago
Birch Cottage was beautifully presented and perfect for a family get together. There was plenty of space, definitely did not feel cramped or on top of each other. The bathrooms were clean and modern, presented with complimentary toiletries. The bedrooms were a good size with adequate storage. The beds were comfortable and the bed linen was pristine. The location of the cottage is stunning, halfway up a hillside with plenty of challenging walks literally on the doorstep. The pool area exceeded expectations. It was modern, clean and warm. Sophie pre-arranged with me the times that the occupants on our cottage would use it and that worked out fine. I would have no hesitation in recommending Birch Cottage and hope to visit again some day.
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.
Guest favourite
Farm stay in Derbyshire
4.85 out of 5 average rating, 20 reviews

Family Home Getaway - Hot Tub, Sauna & Swim Spa

ChristineRating, 5 stars2 weeks ago
Our stay at this beautiful house was most enjoyable. It's very rural. You can't really walk to places if you have young children. Not alot of footpaths. But if you want a nice quiet time to recharge your batteries this is the place. So relaxing. Well worth a visit. Will go back. Thank You. Chris and Hugh Maxwell and Family. 🥰
Guest favourite
Apartment in Bakewell
4.76 out of 5 average rating, 63 reviews

Peak District~ Hot Tub~ Cosy 2 bedroom apartment.

MartinRating, 5 stars2 weeks ago
Fantastic location and lovely accommodation, what more can I say?

Quick stats about holiday rentals that are family-friendly in Chesterfield

  • Total rentals

    50 properties

  • Nightly prices starting at

    $77 AUD before taxes and fees

  • Total number of reviews

    3.3K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 properties include access to Wi-Fi

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