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Holiday rentals with outdoor seating in Chesterfield

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Chesterfield

Guests agree: these rentals with outdoor seating 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 Beeley
4.98 out of 5 average rating, 207 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
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.
Guest house in Derbyshire
4.99 out of 5 average rating, 181 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
The living room features a cozy arrangement with a soft beige sofa and armchair, adorned with floral cushions. A low coffee table sits in front of a fireplace, while patterned curtains frame a bright window. A small TV is mounted on the wall above the fireplace.
Cottage in Chesterfield
4.92 out of 5 average rating, 314 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.

Superhost
A bright studio area features a double bed with soft linens and decorative pillows. A small dining table is set for two, accompanied by a bottle of sparkling wine and glasses. Natural light floods through glass doors leading to an outdoor patio.
Guest suite in Tupton
4.87 out of 5 average rating, 359 reviews

Studio Annexe on the Edge of the Peak District

A bright and airy ground floor annexe, used solely for guests. With its own entrance, a comfortable double bed, fully equipped kitchen and outdoor patio area, you are guaranteed a relaxing and private stay. Nestled away in the village of Tupton on the edge of the Peak District, we hope that you can find a place to relax, eat and explore. If you're with us for work, moving house or to see family, then we have everything you need from pots and pans to a washing machine as well as a space to park.

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, 196 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 modern open-plan living area features a well-equipped kitchen with a marble countertop and dark cabinetry. A vase with fresh roses sits on the counter. A comfortable sofa is observed in the background, alongside a decorative wall with framed artwork and a television.
Loft in Ashover
4.98 out of 5 average rating, 216 reviews

Fairfield Loft, Ashover - Village hideaway for two

Fairfield Loft is in the heart of the lovely village of Ashover with the beautiful Derbyshire Dales and Peak District National Park right on the doorstep. Tucked away behind Stamp, our coffee shop and village post office, the space was renovated in 2021 with comfort and quality in mind. There's lots to see and do in the area but if you simply want to relax then spend the days exploring the many beautiful local walks and maybe wind down with a drink or two in one of the friendly local pubs.

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
4.93 out of 5 average rating, 164 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
Cottage in Butterton
4.98 out of 5 average rating, 133 reviews

Idyllic cottage retreat

This romantic retreat is set in the heart of the picturesque village of Butterton which overlooks the beautiful Manifold Valley in the Peak District. The lanes are lined with pretty sandstone cottages and an idyllic ford runs through the cobbled street below the cottage and a great country pub is round the corner. This cosy hideaway is an ideal couples escape featuring a stunning bedroom with vaulted beamed ceiling and luxury features throughout. It has a boutique hotel feel in rural heaven.

Top 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, 108 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
Apartment in Chesterfield
4.99 out of 5 average rating, 160 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.

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, 342 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
An outdoor terrace features a round white table surrounded by delicate chairs, overlooking lush greenery. Glass railings provide a clear view of the surrounding trees, creating a serene atmosphere. The sun filters gently through the leaves, enhancing the tranquil ambiance.
Home in Darley Dale
5 out of 5 average rating, 106 reviews

Spacious Scandinavian style hideaway with log fire

The property is in a delightful and secluded position on the south facing side of Darley Hillside with views over the valley. The main living area is on the upper floor, accessed directly from the driveway and car-port via a hallway leading to the master bedroom and ensuite; living room with open log fire, dining area and internal balcony access to 2-storey atrium complete with spiral staircase; cloakroom; toilet, and kitchen with tree top external terrace.

Popular amenities for outdoor seating rentals in Chesterfield

When is the best time to visit Chesterfield?

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Avg. price$121 SGD$119 SGD$133 SGD$134 SGD$142 SGD$142 SGD$155 SGD$153 SGD$138 SGD$152 SGD$143 SGD$155 SGD
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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 $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,540 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Chesterfield holiday rentals include wifi 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!