
Holiday rentals in Chesterfield
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chesterfield
Guests agree: these stays 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

The Old Dance Studio
Welcome to our newly renovated apartment in the centre of Chesterfield, where you will be able to relax in style. Modern but full of character, the Old Dance Studio is a bright and spacious 1 bedroom ground floor flat with an open plan living space, kitchen, bathroom and access to a courtyard. Great for anyone commuting or working in the area or visiting the Peak District with a short walk to the train station and town centre. Paid parking from £3.80/24h and on street parking available nearby.

Cosy 2 bed home CHESTERFIELD
This cosy, modern 2 bed home is the perfect base to explore Chesterfield, Derbyshire and the Peak District. Kitchen well equipped with oven, washing machine, large fridge/freezer, toaster, kettle, microwave and all kitchenware. The living room is bright with a large comfy sofa, smart TV and a fold out dining table with 4 chairs. Two double bedrooms, plenty of wardrobe space and bathroom with a walk-in shower. Fast free wi-fi and free parking at the back of the property. EV charging available.

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.

The Garden Room
The Annexe is self contained in the garden of our home in Wingerworth. Private entrance through small conservatory . Shower room , fridge, kettle, toaster , microwave. Cereals, bread, butter and preserves provided. Close to countryside and Peak District National Park . On drive parking. Bus stops nearby to Chesterfield and Derby with links by bus/train from Chesterfield Rail Station. Good local walks and Chatsworth Estate 20 minutes drive. Excellent Pub/Restaurant 5 minutes walk away.

Exclusive & Beautiful Modern Studio Flat
Located on Green Lane, traffic is busy at peak times of the day, however this private studio is perfect for access to the Peak District. There is a kitchen, a spacious bathroom, pull-down double bed (only a small 4 ft double). The flat is best suited for a single person but if you are in a couple and the bed is ok, then this will suit you. The Peak district is just a short car ride away. Restaurants, supermarkets; train station and buses will take you to Sheffield or chesterfield.

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

Self-Catering, Log Burner, Cosy, Peak District
Welcome to Leveret! Our cosy retreat in the heart of the picturesque Peak District. Lovingly designed to provide you with the perfect blend of comfort and rustic charm! Unwind by the crackling warmth of the log burner, while relaxing on the comfortable modern furnishings! Leveret features a well-appointed king-size bedroom, fully equipped kitchen complete with modern appliances, and bathroom with bath and shower over. Private outdoor space & BBQ area in peaceful surroundings.

The Old Bank Luxury Serviced Apartment Derbyshire
This is a 2 bedroom, recently renovated, luxury serviced apartment. We can accommodate up to 4 guests with a super comfy king sized bed with 50” smart TV, 2nd bedroom 2 single beds and 43” smart TV. There is a fully equipped dining kitchen with washer, dishwasher, oven, microwave and table / chairs for 4 people. Stunning en-suite walk in shower room refurbished to the highest standard! Full bathroom with bath and shower. We also offer discounts for stays longer than 2 nights.

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
Popular amenities for Chesterfield holiday rentals
Other great holiday rentals in Chesterfield

Ellie's Place

Lovely room just off Ecclesall Road

Large double with own bathroom.

Beautiful, large double bedroom with own bathroom.

Cosy attic room with dbl bed nr town centre

Crossfield Coach House

Compact clean friendly Millhouses (Tea & Coffee)

Friar tuck cosy single room in Robin Hood country
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $117 SGD | $118 SGD | $121 SGD | $130 SGD | $131 SGD | $131 SGD | $143 SGD | $155 SGD | $135 SGD | $139 SGD | $137 SGD | $130 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 |
Frequently Asked Questions
Are there house rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 30 house rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Chesterfield?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with a kitchen, over 40 homes with free parking, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly house rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 20 house rentals for guests traveling with pets.
Are there family-friendly house rentals in Chesterfield?
Chesterfield has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Chesterfield have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in condo rentals in Chesterfield?
Experience the best of Chesterfield with our condo rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Chesterfield have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Chesterfield?
Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 180 vacation rentals in Chesterfield, and over 180 vacation rentals in Brimington.
Quick stats about holiday rentals in Chesterfield

Total holiday rentals
Explore 100 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 6,960 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
100 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!
Destinations to explore
- London Holiday rentals
- Picardy Holiday rentals
- Hebrides Holiday rentals
- Amsterdam Holiday rentals
- Thames River Holiday rentals
- South West England Holiday rentals
- Inner London Holiday rentals
- Rivière Holiday rentals
- Dublin Holiday rentals
- Brussels Holiday rentals
- South London Holiday rentals
- Central London Holiday rentals
- Apartment rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Flat rentals Chesterfield
- Cottage rentals Chesterfield
- House rentals Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with outdoor seating Chesterfield
- Cabin rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Peak District national park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- The Quays
- Lincoln Castle
- Harewood House
- Sundown Adventureland
- Mam Tor
- Royal Armouries Museum
- Tatton Park
- Holmfirth Vineyard
- Crucible Theatre
- The Nottinghamshire Golf & Country Club
- Science and Industry Museum
- Shrigley Hall Golf Course
- Rufford Park Golf and Country Club
- Cavendish Golf Club
- IWM North
- John Rylands Library
- Derwent Valley Mills
- Daisy Nook Country Park
- Manchester Central Library
- Bosworth Battlefield Heritage Centre




