
Vacation rentals in Chesterfield
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chesterfield
Guests agree: these stays are highly rated for location, cleanliness, and more.

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 Kennels
Kick off your walking boots, wash down your bike or just park up the car, this freshly converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

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.

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.

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.

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.

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.

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.

Rita's Retreat
Rita’s Retreat is set on a working small holding, with lovely views across the fields, and sheep grazing close by. Inside is a handmade double bed, made locally, a full size shower with sink and WC and heated towel rail, well equipped kitchen, comfortable living area and Smart TV. Outside is a decking area with Bistro set and also an area with a fire pit. Not suitable for children Not suitable for pets

'Rose House' Modern 3 Bedroom Detached House
Located a mile from Chesterfield town centre. The property consists of a large open plan lounge/kitchen, 2 double bedrooms and 1 single room with bunk beds. The garden is south facing and there is private parking. There are a range of bars, cafe's, restaurants and local amenities just a short walk from the property. Chatsworth House, Haddon Hall and Peak District are 15 minutes drive away.
Popular amenities for Chesterfield vacation rentals
Other great vacation rentals in Chesterfield

Garden Loft/Studio Sleeps 2

The Annexe - Belle Vue House

Luxury Peak District Cottage with Hot Tub

Wasp Nest Cottage, Peak District

Cosy Grade ll listed cottage Central Peak District

2 Bed Apartment at the Corner House - Town Centre

The Tower

Kingfisher Cottage
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$18,819 GYD | G$19,028 GYD | G$19,447 GYD | G$20,910 GYD | G$21,119 GYD | G$21,119 GYD | G$23,001 GYD | G$24,883 GYD | G$21,747 GYD | G$23,420 GYD | G$22,583 GYD | G$23,001 GYD |
| 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 vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 50 vacation 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 vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 60 family-friendly stays. 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 house rentals in Chesterfield have wifi?
Absolutely! We offer over 60 house 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 vacation rentals in Chesterfield

Total vacation rentals
Explore 110 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at G$6,273 GYD per night before taxes and fees

Verified guest reviews
Over 7,360 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
100 of Chesterfield vacation 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!
Destinations to explore
- Durham Vacation rentals
- London Vacation rentals
- Picardie Vacation rentals
- Sea of the Hebrides Vacation rentals
- Thames River Vacation rentals
- Amsterdam Vacation rentals
- South West Vacation rentals
- Inner London Vacation rentals
- Rivière Vacation rentals
- Dublin Vacation rentals
- Brussels Vacation rentals
- South London Vacation rentals
- Condo rentals Chesterfield
- Cabin rentals Chesterfield
- Cottage rentals Chesterfield
- Rentals with a patio Chesterfield
- Family-friendly rentals Chesterfield
- House rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a washer and dryer Chesterfield
- Apartment rentals Chesterfield
- 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
- Heaton Park
- Mam Tor
- Tatton Park
- Didsbury Village
- Royal Armouries Museum
- Utilita Arena Sheffield
- The Piece Hall
- Crucible Theatre
- Donington Park Circuit
- Wythenshawe Park
- Science and Industry Museum
- Manchester Central Library
- Bowlers Exhibition Centre




