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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
A well-maintained pathway leads to a beautifully designed cottage surrounded by lush greenery. The property features manicured hedges and trees, with a clear blue sky overhead, creating a welcoming entrance to the private garden area.
Guesthouse in Derbyshire
4.99 out of 5 average rating, 192 reviews

Springwood Cottage Private and Unique

Springwood Cottage is ideally situated in a beautiful location on the edge of Derbyshire is completely self contained with its own entrance and private garden area with parking outside. The Cottage is completely newly built in 2020 and designed to the highest standard. Well behaved Dogs welcome, we are happy to accommodate 2 dogs, please request if you have more than 2. A deluxe super kingsized bed (6 x6 foot) with the most up to date memory foam mattress and a comfortable sofa bed in the lounge

Top Guest favourite
Cottage in Chesterfield
4.93 out of 5 average rating, 331 reviews

Chatsworth Cottage

Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

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, 276 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, 229 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, 601 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.

Top 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.

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, 243 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.

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, 365 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
An open-plan living space is presented, featuring a cozy seating area with a blue sofa and armchair. A round dining table for four is set against the wall, while natural light enters through the doorway leading to the garden.
Home in Baslow
4.98 out of 5 average rating, 265 reviews

Peaceful hideaway Baslow Chatsworth, Peak District

Gorse Ridge End is a fresh and airy bungalow superbly situated in the beautiful village of Baslow in the heart of the stunning Peak District National Park. Within walking distance of the Chatsworth Estate, excellent village pubs, restaurants and dramatic gritstone crags and moorlands. In a peaceful village location away from the main road with private garden and plenty of off road parking, this 2 bedroom property provides a tranquil base for a couple or a family.

Top Guest favourite
An outdoor seating area features comfortable lounge chairs on a grassy patio, with a wooden deck extending towards a Japanese whirlpool bath. Large glass doors provide access to the interior, framed by wooden beams under a clear blue sky.
Cabin in Bakewell
4.92 out of 5 average rating, 480 reviews

Air conditioned Woodcutters ~ Romantic Retreat

✨ Romantic Air-Conditioned Cabin with Whirlpool Bath & Couples Spa 💖 Escape to Woodcutters Cabin — a luxury hideaway for two in the heart of the Peak District. Enjoy your private Japanese whirlpool bath with mood lighting, a plush super-king bed, and a secret shower-room door. Treat yourselves to candle-lit couples massages in our tranquil treatment room. A peaceful, baby, child-free, pet-free retreat made for romance and total relaxation.

Popular amenities for Chesterfield outdoor seating rentals

When is the best time to visit Chesterfield?

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