Family-friendly holiday rentals in Chesterfield

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chesterfield family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home
4.96 out of 5 average rating, 342 reviews

Hunters Cottage. Wheatsheaf Mews

KathleenRating, 5 stars1 day ago
Jennie greeted us and let us into her wonderful property, showing us the best places to take walks and visit in the area. An extremly lovely house to come back to after long walks or day trips out and even had the perfect weather to enjoy the hot tub. It was just two of us staying in the property so more than enough room for anyone with a party of 4 looking to book somewhere - a positive and amazing first Air BnB experience, highly recommend to anyone thinking of staying here!
Guest favourite
Cottage
4.88 out of 5 average rating, 552 reviews

HOT TUB Luxury Converted Barn

IyeshaRating, 5 starstoday
We had a lovely time such a beautiful property very clean comfy beds and we will defo visit again and recommend thank you Scott you was amazing :)
Superhost
Cottage
4.75 out of 5 average rating, 79 reviews

Midhope Lodge Luxury Barn Conversion with hot tub

MattRating, 5 stars8 months ago
Everything was as expected, everything a guest needed was anticipated
Guest favourite
Barn
5 out of 5 average rating, 22 reviews

The Stables 1 bedroom with Private Hot Tub

AmyRating, 5 stars2 days ago
Absolutely loved the two days! Was a great time to spend with my mum! The hot tub, the view the amenities! Andrea was incredibly friendly!! Deffo recommend anyone staying here in the future
Superhost
Home
4.9 out of 5 average rating, 48 reviews

Cottage by the Pond Self Catering

YuRating, 5 stars4 days ago
We spent three nights at Sue’s farmhouse and it couldn’t be better. It is quite remote which means peace and fresh air, but also accessible to Ashbourne for food and restaurants. The beds are very comfortable (considering myself to be quite picky with beds and pillows). The kitchen is very well equipped and we had everything we need for cooking dinner. Thanks for your hospitality and we really enjoyed our stay.
Guest favourite
Farm stay
4.92 out of 5 average rating, 78 reviews

Entire home - Garden Cottage, Loversall

RebeccaRating, 5 stars5 days ago
Had a great weekend stay here. Such a beautiful cottage with lovely surroundings.
Superhost
Home
4.92 out of 5 average rating, 105 reviews

A beautiful Victorian Manor House, Nottinghamshire

ClaireRating, 5 stars4 months ago
We stayed in the Manor for Christmas Eve and Christmas Day with our relations from Australia. We had a fantastic stay! The rooms were a perfect size and could fit us all in for games and entertaining ourselves, the kitchen was fully stocked with all the crockery and glassware we needed, the children loved the games room and the hot tub and the house was beautifully adorned with Christmas decorations. We all thoroughly enjoyed our stay in this characterful house.
Top guest favourite
Farm stay
4.94 out of 5 average rating, 367 reviews

The Dairy, stunning views & close to Alton Towers

PeteRating, 5 stars2 weeks ago
Excellent stay with our two toddlers (3 and 1). Great little place that is bigger than it seems on the photos! Our kids loved seeing the animals roaming around. Perfeclty located for alton towers too!

Family- and pet-friendly home rentals

Top guest favourite
Cottage
4.96 out of 5 average rating, 331 reviews

The Barn @ Dale End House, Gratton nr Bakewell

SarahRating, 5 stars2 weeks ago
Gorgeous place to stay. Views from every window. Expect family ducks, chickens and peacock to pay you a visit, and if you hear snoring, it’s probably the large pig outside the window!
Superhost
Home
4.77 out of 5 average rating, 293 reviews

Forge Cottage Chinley Peak District

JeannetteRating, 5 stars1 month ago
Great accommodation. Great location. Just as described. Terri was responsive, friendly and helpful xxx
Guest favourite
Cottage
4.87 out of 5 average rating, 332 reviews

Thistledown Cottage, Snitterton near Matlock

JennyRating, 5 stars1 week ago
What an incredible place! We fell in love with it. We were given excellent instructions prior to arrival and the owners came to say hi with the horses which my children loved. They also made friends wirh the two dogs and cat. The cottage has everything you could need, was really warm and cosy and had a lovely modern kitchen. The location is perfect, peaceful with no noise but close to Matlock. The lambs in the field next door were gorgeous! We will definitely be back, honestly couldnt fault it xxx
Guest favourite
Cottage
4.9 out of 5 average rating, 125 reviews

Whitwell character house 20 mins to Peak District

AnnRating, 5 stars1 month ago
I know the area and needed a place to stay. The home was welcoming and warm. Everything you could need was available. It was clean and tidy. There was plenty of space, so if I had been travelling with family it would still have been big enough
Guest favourite
Home
4.93 out of 5 average rating, 176 reviews

Large House Nr Ashbourne

VaidaRating, 5 stars1 month ago
wow, I was amazed with the views, the size of kithen and dinning area, rooms, numbers of toilets! it was all what we were looking for. The energy of house itself was very positive! thank you for a lovely stay!
Guest favourite
Cottage
4.87 out of 5 average rating, 160 reviews

Harry Eyre Cottage, Castleton, Peak District

DeanRating, 5 stars4 days ago
We had a lovely 4 nights stay at the cottage with our two dogs. The cottage was clean and we had everything we would need for our stay, including wood for the log burner. The enclosed garden was a nice place to sit and enjoy wonderful views and to watch the sunset with a glass of wine. Castleton is only a 15min walk along a footpath from the rear of the cottage and there are plenty of places to eat and drink in the village. We will definitely be back soon. Highly recommended 👌
Top guest favourite
Cottage
4.99 out of 5 average rating, 107 reviews

The Old Toffee Shop

KateRating, 5 stars5 months ago
An amazing property, best I’ve booked on Airbnb. Beautifully presented, extremely clean and very well stocked. You can tell the love and care that has gone into creating this rental and Julie clearly has very good taste. Everything you could possibly need - Julie has included it and she’s gone the extra mile with lovely extra touches. The cottage is well located right in the heart of Tideswell with walks and restaurants on your doorstep. If you have a dog, the boot room outside is fantastic with its warm shower and Julie even supplies dog towels and shampoo. I cannot recommend this property enough and we’ll most certainly be back!
Guest favourite
Cottage
4.87 out of 5 average rating, 104 reviews

Rubicon, The Lookout Cottages

ColbyRating, 5 stars1 month ago
Honestly couldn’t recommend more! Better than the photos + host was very accommodating with check-in/check-out.

Family-friendly home rentals with a pool

Guest favourite
Home
4.85 out of 5 average rating, 48 reviews

Charming 6-Bedroom Winster Village, Peak District

HannahRating, 5 stars1 week ago
We had a large group stay for 2 nights, and found that the communal spaces worked really well. We appreciated having enough space for people to sit and eat together, with a separate lounge area that was similarly big enough for everyone to comfortably gather. The beds were comfortable, and the flexibility of the layout was appreciated. We had a nice meal out that was only 10mins drive away, and enjoyed the nice walks in the area. Communication from the host was responsive. There is only one small parking space at the property but there was plenty of on-street parking within close proximity.
Top guest favourite
Cottage
4.95 out of 5 average rating, 335 reviews

Luxury Peak District Home - 2 miles from Ashbourne

JamesRating, 5 stars1 week ago
Fantastic luxury cottage. Ideal for exploring the Peak District. Great hosts and property for two little children to explore!
Home
4.8 out of 5 average rating, 10 reviews

Haddon Grove Farmhouse - with pool & lots of heart

OliverRating, 5 stars3 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.
Superhost
Cottage
4.7 out of 5 average rating, 46 reviews

Birch Cottage

PhilipRating, 5 stars2 weeks 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
4.86 out of 5 average rating, 7 reviews

The Manor House

EiraRating, 5 stars36 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.
Top guest favourite
Farm stay
4.93 out of 5 average rating, 14 reviews

Family Home Getaway - Hot Tub, Sauna & Swim Spa

CarlyRating, 5 stars1 week ago
We had a fantastic break. 2 families with kids of different ages and the dogs of course. There was more than enough space for all of us, and the house was kitted out perfectly. We absolutely loved the swim spa and hot tub. We would definitely book the house again.
Home
4.64 out of 5 average rating, 11 reviews

Badgers Wood

JackRating, 5 stars44 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.
Top guest favourite
Flat
4.75 out of 5 average rating, 60 reviews

Peak District~ Hot Tub~ Cosy 2 bedroom apartment.

HannahRating, 5 stars3 weeks ago
We had an absolutely wonderful stay! The cottage is charming and cozy—perfect for a weekend escape from the hustle and bustle of everyday life. The location is stunning, and we especially loved relaxing in the impressive hot tub while taking in the breathtaking views. It made for a truly special Mother’s Day weekend, and we can’t wait to return in the future. Thank you so much!

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

  • Total rentals

    50 properties

  • Nightly prices starting at

    £38 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

  • Wifi availability

    50 properties include access to wifi

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