
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.

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.

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

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.

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.

Chesterfield -Peak District-Chatsworth-EV Charger
Enjoy 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.

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

Charming grade II listed cottage with hot tub
Chander Hill Cottage is a stylish 3-bedroom barn conversion nestled above the village of Holymoorside, on the edge of the Peak District. This cosy cottage is a perfect base for exploring the countryside, with numerous walks from the door and two pubs just a mile away in the village. Relax in our hot tub with stunning views or warm up by the wood burning stove after a winter walk. The enclosed cottage garden has a patio where you can enjoy a BBQ in the summer. Dogs welcome!

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.

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.

Cosy Grade ll listed cottage Central Peak District
Nestled in the picturesque village of Monyash, Mereview a Grade II listed stone cottage offers the perfect escape for couples or solo adventurers seeking peace, character, and countryside charm. Thoughtfully restored and beautifully presented, this historic home blends timeless elegance with modern comfort. Whether you’re walking the limestone dales, visiting nearby Bakewell or Chatsworth House, or simply curling up with a book by the fire, this cottage is a serene base.

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 outside

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. 1 mile from the Derbyshire countryside, 10miles - Chatsworth House, 12 miles - Bakewell.
Popular amenities for outdoor seating rentals in Chesterfield
House rentals with outdoor seating

Cosy terrace house in Worksop town centre

Country Cottage with great outside space & views

Cosy house with spectacular views in Matlock

Bridgefoot Cottage - Wild Swimming & Hot Tub

Cosy cottage, stunning views near Chatsworth

Charming fully equipped home 5min to Peak District

The Entire Coach House at Middleton Hall

The Old Coach House. 5-star. Parking. EV charger.
Apartment rentals with outdoor seating

Flat in Lady Bay &free parking - Riverside retreat

Spacious City Centre apt/parking and balcony

Garden studio in Antiques quarter

La Terraza 2 bed with balcony. Nottingham hockley

1 Dalebrook View, Stoney Middleton

The Coach House Harthill

Beautiful & open plan studio apartment - sleeps 2

Corbar Bank: Contemporary Central Buxton Apartment
Apartment rentals with outdoor seating

Lovely 1 bed apartment, parking & rural views

Fabulous vintage vibe - Sheffield & Peak District!

Large self contained garden apartment

Stylish, Opulent & Spacious 18C. Peaks apartment

House of Suede in the Heart of Kelham Island

Fairwinds

Dale side apartment

Large 1 Bedroom Apartment, Broomhill
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $121 SGD | $118 SGD | $132 SGD | $134 SGD | $141 SGD | $141 SGD | $154 SGD | $153 SGD | $137 SGD | $131 SGD | $123 SGD | $141 SGD |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
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!
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- Peak District National Park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- AO Arena
- The Quays
- Manchester Central Convention Complex
- Motorpoint Arena Nottingham
- First Direct Arena
- Lincoln Castle
- Harewood House
- Mam Tor
- Tatton Park
- Didsbury Village
- Royal Armouries Museum
- Leeds Grand Theatre and Opera House
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- The Whitworth
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