Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Guest favorite

Cottage in Chesterfield

4.92 out of 5 average rating, 222 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.

Aug 26 – Sep 2

G$28,738 GYD per night

Guest favorite

Guest suite in New Tupton

4.85 out of 5 average rating, 254 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.

Sep 6 – 13

G$14,511 GYD per night

Guest favorite

Apartment in Sheffield/Chesterfield

4.99 out of 5 average rating, 142 reviews

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. September 2021 - daytime noise redevelopment of adjacent barn.

Jun 11 – 18

G$16,850 GYD per night

Guest favorite

Guest suite in Ashover

4.97 out of 5 average rating, 273 reviews

Hunger Hill Farm Studio - Derbyshire Dales

Set in the glorious Peak District in a rural location is our lovely self contained studio. Glorious views over rolling countryside and very close to Chatsworth House and Stanedge Golf Club, you are guaranteed a peaceful stay here. With a lovely country pub, the very popular wedding venue of the 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.

Mar 15 – 22

G$20,066 GYD per night

Guest favorite

Home in Wingerworth

4.9 out of 5 average rating, 198 reviews

Oakdale - Our Quest retreat

Idyllically situated at the entrance to Hardwick Wood, Wingerworth, 2 miles from Chesterfield and all amenities, yet totally secluded. Close to Chatsworth & Peak District. Fully fitted kitchen all appliances including tumble drier & dishwasher. Underfloor zoned central heating. Log burner. Fully fitted bathroom with bath and shower. Separate shower/wc. Fully fitted bedrooms with ample wardrobes and drawers ideally suited to a family of 4. Sleeps 4 in one double and 1 set of bunks, cot available

Jul 5 – 12

G$18,004 GYD per night

Guest favorite

Cottage in Holymoorside

4.97 out of 5 average rating, 218 reviews

Wasp Nest Cottage, Peak District

Sitting on the edge of the Peak District, a stone’s throw from open fields, woodland and moors - sits a 19th Century cosy mill worker’s cottage. Two pubs and a shop are within easy walking distance and Chatsworth House is a beautiful 7 mile wander over the hill. Marvel at the lovely centuries old tree slice, coffee table and huge slice of elm breakfast bar, enjoy chopping boards, pottery and soft furnishings from the local artisans - just some of the magic the Peak District has to offer.

Oct 1 – 8

G$30,001 GYD per night

Guest favorite

Apartment in Chesterfield

4.96 out of 5 average rating, 242 reviews

Cosy studio apartment close to Peak District

Cosy,private ,self contained upstairs studio with own entrance , double bed with en suite, dual ring halogen hob ,combination microwave and oven , television with free sat ,free wifi ,integrated fridge freezer ,breakfast bar and stools . Comfy chairs to relax! On the main bus route into Chesterfield and the Peak District ,10 mins to Chatsworth,20 mins to Bakewell and lots of walks in the area. Many bars ,coffee shops and restaurants within walking distance . We look forward to meeting you.

Mar 14 – 21

G$19,172 GYD per night

Guest favorite

Guest suite in Wingerworth

4.93 out of 5 average rating, 192 reviews

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.

Aug 10 – 17

G$10,801 GYD per night

Guest favorite

Condo in Dronfield

4.82 out of 5 average rating, 206 reviews

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.

Jan 2 – 9

G$11,697 GYD per night

Guest favorite

Farm stay in Derbyshire

4.96 out of 5 average rating, 127 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 outside

Feb 20 – 27

G$18,129 GYD per night

Guest favorite

Home in Walton

4.84 out of 5 average rating, 302 reviews

Perfect For The Peak District and Chatsworth!

This beautiful townhouse is right on the edge of The Peak District and only minutes from Chatsworth House. This stylish space has everything you need for the perfect getaway for 2 and is a perfect base for visiting all the attractions nearby. A short walk away you will find some wonderful bars and restaurants, artisan gift shops, designer clothing boutiques and if you like a game of golf, Chesterfield Golf club is only a mile away.

Apr 28 – May 3

G$16,110 GYD per night

Guest favorite

Guesthouse in Derbyshire

4.97 out of 5 average rating, 169 reviews

The Annexe - Belle Vue House

The Annexe to Belle Vue House was built for Servants to the main house in 1823. The grade 2 listed building commands an elevated position overlooking Matlock Bath. The property has been lovingly updated to keep period features while providing modern living. The property is accessible via a flight of stone stairs from the lower drive way. Due to the period nature and historic listing road side parking is necessary.

Oct 26 – Nov 2

G$19,722 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chesterfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chesterfield's top sights

Morrisons5 locals recommend

Queens Park5 locals recommend

Queen's Park Sports Centre3 locals recommend

Chesterfield Parish Church16 locals recommend

Cineworld Cinema Chesterfield19 locals recommend

Chesterfield Market8 locals recommend

Other great vacation rentals in Chesterfield

Guest favorite

Home in Derbyshire

4.97 out of 5 average rating, 99 reviews

Florries House is on the edge of the Peak District

Jan 20 – 27

G$10,077 GYD per night

Guest favorite

Townhouse in Derbyshire

4.87 out of 5 average rating, 75 reviews

Cottage by the Park Chesterfield - Peak district

Oct 11 – 18

G$23,510 GYD per night

Guest favorite

Home in Derbyshire

4.81 out of 5 average rating, 47 reviews

Bright - 2 Bedroomed House in Derbyshire

Oct 7 – 14

G$20,415 GYD per night

Guest favorite

Home in Derbyshire

4.95 out of 5 average rating, 22 reviews

Cosy 2 bed home CHESTERFIELD

May 13 – 20

G$23,432 GYD per night

Superhost

Apartment in Dronfield

4.91 out of 5 average rating, 35 reviews

The Old Bank Luxury Serviced Apartments, Dronfield

Nov 3 – 10

G$19,845 GYD per night

Guest favorite

Home in Derbyshire

4.99 out of 5 average rating, 93 reviews

Home from Home with private rose garden

Oct 20 – 27

G$28,177 GYD per night

Guest favorite

Home in Derbyshire

4.88 out of 5 average rating, 49 reviews

Family Fun Party House! Pool, Bar, Sauna, Cinema.

Mar 30 – Apr 6

G$220,891 GYD per night

Guest favorite

Home in Brimington

5.0 out of 5 average rating, 8 reviews

Annexe to my Bungalow

May 6 – 13

G$17,786 GYD per night

Show all

Quick stats about vacation rentals in Chesterfield

Total rentals
100 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
5.5K reviews
Nightly prices starting at
G$4,179 GYD before taxes and fees

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 50 homes with wifi, over 40 homes with free parking, 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 30 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 apartment rentals in Chesterfield?
Experience the best of Chesterfield with our apartment rentals, starting at about $40 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 50 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 170 vacation rentals in Brimington CP, and over 170 vacation rentals in Chesterfield.

Vacation rentals in Chesterfield

Top-rated vacation rentals in Chesterfield

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Chesterfield vacation rentals

Stay near Chesterfield's top sights

Other great vacation rentals in Chesterfield

Home in Derbyshire

Townhouse in Derbyshire

Home in Derbyshire

Home in Derbyshire

Apartment in Dronfield

Home in Derbyshire

Home in Derbyshire

Home in Brimington

Quick stats about vacation rentals in Chesterfield

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chesterfield?

What are the most popular amenities for House Rentals in Chesterfield?

Are there pet-friendly vacation rentals in Chesterfield?

Are there family-friendly vacation rentals in Chesterfield?

Do house rentals in Chesterfield have a kitchen?

How much does it cost to stay in apartment rentals in Chesterfield?

Do house rentals in Chesterfield have wifi?

Where should I stay in Chesterfield?

Destinations to explore