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Family-friendly holiday rentals in Chesterfield

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chesterfield

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A traditional stone barn conversion is visible, showcasing a well-maintained exterior with multiple windows and doors. The surrounding gravel driveway leads to a serene countryside setting, highlighted by greenery in the background and a clear blue sky above.
Apartment in Holymoorside
4.98 out of 5 average rating, 220 reviews

Dog Friendly, Cosy, Peaceful, Walks, Peak District

The Spinney is our super dog-friendly ground floor self-catering accommodation! We've designed it so that you & your dog have a great holiday! Part of a traditional stone barn conversion located in the Peak District & Derbyshire Dales, the Spinney offers space as well as the comfort of modern living. With cosy underfloor heating throughout, and everything you need for you and your furry friend, we are sure you will have a great time here! Peaceful setting, close to popular visitor attractions!

Top guest favourite
Home in Rowsley
4.98 out of 5 average rating, 294 reviews

Panoramic views, Spring Lambs, Bakewell Chatsworth

The Garden Nook offers complete privacy and is located in a perfect spot for everything. Newly converted and set within 55 acres of impressive private land, gardens, and fruit orchards. A rejuvenating location to unwind and reconnect with nature in such a tranquil environment. The comfy contemporary haven with tasteful decoration, stylish furniture, and spectacular views is the perfect place to relax. Watching lambs skipping around the orchard is a delightful bonus! Tractor experiences available

Guest favourite
The renovated stone barn features a tidy exterior with a porch and flower beds filled with colorful plants. A gravel driveway leads to the entrance, and a spacious lawn area is visible. The surrounding hills create a serene countryside backdrop.
Home in Derbyshire
4.9 out of 5 average rating, 190 reviews

Cheerful 2-bedroom home with free offroad parking

Explore all the peaks has to offer with this beautifully renovated field barn. Free offroad parking, garden area. Two bedrooms, two bathrooms. Open plan downstairs gives a airy homely feel. Within easy access of footpaths and trails close to the famous quarries of derbyshire dollermite and limestone. Secluded location yet within easy reach of Wirksworth the nearest town just 5 minutes away and the beautiful village of carsington just over the hill. 2.3m Wirksworth 5.8m Matlock 1.6m Carsington

Top guest favourite
The Tower emerges from a lush green landscape, surrounded by tall trees and manicured grass. The building's robust concrete structure is accented by its original window designs, reflecting the natural beauty of the outdoors in a tranquil setting.
Tower in Bolsover
5 out of 5 average rating, 221 reviews

The Tower

The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

Guest favourite
A modern, light-filled living area features a gray sectional sofa adorned with colorful, geometric pillows. A simple wall-mounted shelf is visible on the left, and a front door, partially open, allows natural light to enter the space.
Townhouse in Chesterfield
4.92 out of 5 average rating, 177 reviews

Cheerful 2- Bedroomed Home in Chesterfield.

This beautiful town house is located right on the edge of the Peak District and within walking distance to Chesterfield's iconic Market Town. This 2 bedroomed modern home has everything you need and is the perfect base for visiting all the local attractions Derbyshire has to offer. The locations boasts a 20 min drive to the well loved Peak District. Along with all the wonderful bars, restaurants, gift & coffee shops just a short walk away. Chesterfield's Golf course is just 15min drive away.

Top guest favourite
A stone exterior of the building is highlighted, featuring a prominent navy-blue door framed by two windows. Soft lighting enhances the entrance, surrounded by a neatly landscaped area with low shrubs and pavers leading to the door.
Cottage in Matlock
4.99 out of 5 average rating, 270 reviews

The Kennels

Kick off your walking boots, wash down your bike or just park up the car, this freshly converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

Top guest favourite
Apartment in Chesterfield
4.99 out of 5 average rating, 181 reviews

Chesterfield -Peak District-Chatsworth-EV Charger

Welcome to our ground floor studio, private entrance, bathroom, kitchenette with fridge freezer, microwave, double bed, wall-mounted TV. PAYG EV Charger - Ideal for business travellers and couples seeking a relaxing break. Located on a quiet, tree-lined avenue. Minutes from Chatsworth Road's bars and restaurants. Close to the Peak District, Chatsworth House, Buxton, Bakewell, and Matlock, guest access via a coded key lock. Nestled near the Hipper Valley bike trail for a peaceful retreat.

Top guest favourite
A wooden lodge is illuminated by warm light in the evening dusk, surrounded by a wooden fence. Softly glowing string lights outline the perimeter, while purple flowers are visibly present in the foreground, adding a pop of color to the serene scene.
Farm stay in Derbyshire
4.95 out of 5 average rating, 353 reviews

Woolley Lodge Farm Retreat

A brand new fully furnished wooden lodge situated within the grounds of a working farm, with views across open countryside. The cabin has been furnished to a high standard and includes a double bedroom with double bed. The kitchen has a full size fridge with small freezer, full size oven and a microwave. It has a small bathroom with a full size corner shower. It has its own entrance, parking and a beautiful decked area and fire pit and BBQ . Not suitable for children or pets

Top guest favourite
Guest suite in Ashover
4.98 out of 5 average rating, 379 reviews

Cosy self contained studio - Peak District

Set in the glorious Peak District in a rural and peaceful location is our lovely self contained studio. Glorious views and walks over rolling countryside. Close to Chatsworth House and Haddon Hall. With the popular wedding venue (Peak Edge Hotel ) within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here. Perfect for the Chatsworth Christmas market.

Top guest favourite
The cabin on wheels is nestled within a lush green meadow, surrounded by dense woodland. Its sloped wooden roof features large windows, allowing natural light to illuminate the interior. A small porch leads to the entrance, complemented by steps for easy access.
Tiny home in Kings Clipstone
4.97 out of 5 average rating, 123 reviews

New Lodge Cabin

A cabin on wheels, made from locally sourced oak and larch. Set within a meadow, surrounded by woodland in Sherwood Forest. Shower with underfloor heating in a shepherd hut. Compost toilets. Outdoor pot washing facilities and dining area. A perfect off grid stay. Our smallholding has sheep, goats and chickens which graze often in the meadow depending on the season. Sherwood Forest and Sherwood Pines are all within walking/cycle distance.

Superhost
The living area features a comfortable gray sofa, accompanied by decorative cushions. A light wooden bookshelf holds various books, while a dining table adorned with a vase of roses occupies the foreground. The space is filled with natural light from nearby windows.
Apartment in Chesterfield
4.83 out of 5 average rating, 141 reviews

The Corner House A-2 Bedroom Town Centre Apartment

A stylish ground-floor apartment in a beautifully converted 1800s home, recently refurbished to a high standard and exclusively used for Airbnb guests. The property features two double bedrooms, a full bathroom plus a separate toilet, and a fully equipped open-plan kitchen/diner with a sofa bed - perfect for relaxing stays. Within walking distance of Chesterfield town centre and train station, with allocated parking for one car.

Top guest favourite
A vibrant green snooker table is positioned in the center of the games room. A triangle of red balls rests at one end, with a single black ball placed nearby. A large television and seating area are visible in the background.
Home in Ecclesfield
4.99 out of 5 average rating, 183 reviews

Exclusive Detached Retreat+Games Room M1J35 1.5m

A unique duplex property that has a fully furnished games room complete with snooker table, professional air hockey table, surround sound cinema system with a self contained upstairs living space equipped to a high standard. Located in the heart of Ecclesfield you are a short distance from local amenities, woodland walks, pubs and cafes but also only a short distance to the vibrant nightlife in Sheffield. .

Popular amenities for Chesterfield family-friendly rentals

When is the best time to visit Chesterfield?

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Avg. price$153 SGD$171 SGD$172 SGD$142 SGD$149 SGD$154 SGD$162 SGD$171 SGD$155 SGD$155 SGD$150 SGD$158 SGD
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Quick stats about holiday rentals that are family-friendly in Chesterfield

  • Total holiday rentals

    Explore 70 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,260 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of Chesterfield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesterfield rentals

  • 4.8 Average rating

    Chesterfield stays are highly rated by guests – averaging 4.8 out of 5!