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Holiday rentals with outdoor seating in Chesterfield

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Quick stats about holiday rentals with outdoor seating in Chesterfield

  • Total holiday rentals

    Explore 40 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $43 AUD per night before taxes and fees

  • Verified guest reviews

    Over 4,750 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chesterfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesterfield rentals

  • 4.9 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated Holiday Houses with Outdoor Seating in Chesterfield

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Rowsley
4.98 out of 5 average rating, 301 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

Top Guest favourite
A spacious lawn leads to a charming stone cottage, surrounded by well-maintained greenery. The bright blue sky and scattered clouds enhance the inviting atmosphere, while the driveway provides access to the property and its scenic surroundings.
Cottage in Derbyshire
5 out of 5 average rating, 277 reviews

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

*AirBnB Best New Host Finalist 2022* A stunning 2 bedroom (Sleeps 4) luxury cottage, nestled in the Peak District countryside, with superb views over Chatsworth House. Outdoor dining, farm animals, private parking (with electric charging) & tranquil walks - all within a short drive of Bakewell, Matlock & the beautiful Derbyshire Dale villages. Fully equipped with everything you will need for your stay, including: Netflix, Amazon Prime & Disney+ BBQ for outdoor dining. Family & Dog Friendly

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, 230 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.

Top Guest favourite
A spacious room features a large bed with gray bedding and decorative pillows. A cozy armchair in a rich maroon color adds warmth next to an elegant glass table. Natural light enters through arched doors leading to a garden, enhancing the peaceful ambiance.
Apartment in Sheffield
4.98 out of 5 average rating, 602 reviews

The Hollies - Luxury self contained apartment

This garden flat with separate access is located in the heart of Sheffield's academic and healthcare hubs. Nestled between Broomhill, Ecclesall road and 2 miles away from the city centre. Close to Botanical Gardens, Endcliffe park and a short walk to a variety of restaurants and pubs. With an en-suite bathroom, well equipped kitchen and small private patio this apartment is perfect for everything Sheffield has to offer! We have 2 friendly dogs and a cat. We also have free overnight parking.

Guest favourite
A charming two-story cottage is presented with a welcoming façade featuring pale pink and cream walls. A quiet street is visible alongside, with a parking space indicated. Lush trees line the road, enhancing the serene environment of the neighborhood.
Townhouse in Chesterfield
4.87 out of 5 average rating, 113 reviews

Cottage by the Park Chesterfield - Peak district

Our COTTAGE is situated with a PARK on our doorstep and 15 min drive to Baslow in the PEAK DISTRICT . Also within walking distance to Chesterfield town center and Chatsworth road. Only a 15 min walk to bars, restaurants, coffee shops, and local boutique shops on Chatsworth Road. It is a short drive to Chatsworth house, Bakewell, Matlock and many of the delightful areas in the Peak district. Our home is cozy and welcoming! We hope you will choose us for your next visit to the area.

Guest favourite
An inviting living space is featured, showcasing a modern dining table and chairs alongside a vibrant red sideboard. A cozy armchair and a striped lounge chair add comfort, while softly illuminated pendant lights enhance the room's ambiance. Natural light filters through a window adorned with gray curtains.
Home in Chesterfield
4.91 out of 5 average rating, 110 reviews

Bright - 2 Bedroomed House in Derbyshire

Your family will be close to everything when you stay at this centrally located town house within walking distance from 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. Right on the edge of the Peak District it boasts a 20 minute drive to Chatsworth House and many more. Along with all the wonderful bars, restaurants, gift & coffee shops all within walking distance.

Top Guest favourite
The exterior of the Coach House features a charming stone facade with a moss-covered roof. Two garage doors, framed by flower pots, provide a warm welcome. A gravel driveway surrounds the building, complementing the tranquil setting among mature trees.
Apartment in Harthill
4.98 out of 5 average rating, 152 reviews

The Coach House Harthill

The Coach House is the beautifully converted annex of ‘The Old Rectory’; a very handsome Grade II listed seven-bedroom period home built by the son of the 1st Duke of Leeds back in 1720, in the pretty village of Harthill. It offers the perfect location to explore Sheffield and the surrounding Peak District, conveniently situated close to the M1 (Junction 30) and A57. The bright and spacious living area comprises a kitchen, bathroom and two bedrooms and has off road parking for two cars.

Top Guest favourite
A bright and open studio space features a comfortable double bed with crisp white linens. A cozy seating area includes soft armchairs and a dining table set for four. Light wood accents and a floral wallpaper create a calming ambiance.
Apartment in Dronfield
4.99 out of 5 average rating, 210 reviews

Peaceful setting, close to amenities and transport

The Milking Parlour is a single storey studio, it is in a quiet enclave composing of a farmhouse, and various renovated farm buildings making up 4 residences. We are situated about 50m from the main road and bus stops for regular direct buses to Sheffield/Chesterfield . Dronfield has a train station providing an hourly service direct to London plus regular trains to Sheffield and Chesterfield. 1 mile from the Derbyshire countryside, 10miles - Chatsworth House, 12 miles - Bakewell.

Guest favourite
A comfortable living area is furnished with a gray sectional sofa and two leather armchairs. A glass coffee table is positioned centrally, and a wooden cabinet stands against the wall, adding storage space. Double doors lead to the outside, allowing natural light to enter.
Home in Chesterfield
4.96 out of 5 average rating, 346 reviews

The Long Hall 2 bed ground floor annexed apartment

Long Hall has been lovingly converted into a 6-person, ground floor, annexed apartment, within a quiet housing estate, a short distance from the Peak District. Two large double bedrooms, with rainfall shower en-suites, and a large open-plan living area dining and kitchen area and a large, shared enclosed patio and garden area Long Hall suits leisure and tourist staycations, as well as trade or professional workers, who wish for a home from home. SKY Sports and Movies included

Top Guest favourite
A serene sleeping area features a wooden bed dressed with a yellow patterned throw, complemented by fluffy towels. A cozy armchair provides additional seating. Large windows frame the view, allowing natural light to illuminate the space, while warm tones create a peaceful ambiance.
Guest suite in Ashover
4.98 out of 5 average rating, 244 reviews

Self-contained studio in amazing rural location

This comfortable studio with amazing views, lots of outdoor space, walks from the doorstep and pubs with good food nearby is perfect for couples looking to re-charge their batteries in a rural location. It has a well-equipped kitchen, including dishwasher, White Company linen, underfloor heating with independent controls, it's own combi-bolier for hot water, tv and wi-fi. It is on the edge of the Peak District with many local attractions, such as Chatsworth and Hardwick Hall.

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
4.94 out of 5 average rating, 369 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

Guest favourite
The stone facade of the barn conversion is complemented by a charming archway entrance. Lush green plants are positioned around the door, enhancing the inviting appearance. A cobbled pathway leads towards the entrance, framed by carefully landscaped gardens and a clear blue sky overhead.
Cottage in Barlow
4.85 out of 5 average rating, 294 reviews

Old Barn Conversion close to the Peak District

This beautiful detached barn conversion has been charmingly renovated, retaining and working with many original features where possible. Tastefully furnished to a very good standard throughout, the open-plan living space has a small/compact kitchen area with a combi/microwave oven and hob. Its stunning beamed vaulted ceiling creates a warm and cosy social environment.

Popular amenities for Chesterfield outdoor seating rentals

When is the best time to visit Chesterfield?

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