Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Chesterfield

4.92 out of 5 average rating, 217 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 13 – 20

€ 138 per night
Guest favorite

Guest suite in Ashover

4.97 out of 5 average rating, 268 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 18 – 25

€ 96 per night
Guest favorite

Home in Wingerworth

4.91 out of 5 average rating, 193 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

Sep 18 – 25

€ 86 per night

Popular amenities for Chesterfield vacation rentals

Stay near Chesterfield's top sights

Morrisons5 locals recommend
Queens Park5 locals recommend
Queen's Park Sports Centre3 locals recommend
Cineworld Cinema Chesterfield19 locals recommend
Chesterfield Market8 locals recommend
TK Maxx3 locals recommend

Other great vacation rentals in Chesterfield

Guest favorite

Cottage in Derbyshire

4.97 out of 5 average rating, 417 reviews

Kingfisher Cottage

Sep 6 – 13

€ 120 per night
Guest favorite

Home in Derbyshire

4.8 out of 5 average rating, 44 reviews

Bright - 2 Bedroomed House in Derbyshire

Jul 13 – 20

€ 89 per night
Guest favorite

Townhouse in Derbyshire

4.86 out of 5 average rating, 74 reviews

Cottage by the Park Chesterfield - Peak district

Nov 26 – Dec 3

€ 113 per night
Guest favorite

Home in Derbyshire

4.97 out of 5 average rating, 96 reviews

Florries House is on the edge of the Peak District

Feb 27 – Mar 6

€ 54 per night
Superhost

Apartment in Dronfield

4.91 out of 5 average rating, 35 reviews

The Old Bank Luxury Serviced Apartments, Dronfield

Sep 10 – 17

€ 95 per night
Guest favorite

Home in Derbyshire

4.88 out of 5 average rating, 48 reviews

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

Sep 4 – 11

€ 1,032 per night
Guest favorite

Guest suite in Derbyshire

4.97 out of 5 average rating, 38 reviews

The Loft

Aug 31 – Sep 7

€ 104 per night
Guest favorite

Home in Dronfield Woodhouse

5.0 out of 5 average rating, 15 reviews

FIELD VIEW Stylish Home near Sheffield & The Peaks

Nov 2 – 9

€ 140 per night
Guest favorite

Home in Derbyshire

4.99 out of 5 average rating, 90 reviews

Home from Home with private rose garden

Jun 15 – 22

€ 133 per night
Guest favorite

Guest suite in Holmesfield

4.96 out of 5 average rating, 46 reviews

One Bedroom Studio with full kitchen & log burner.

Oct 1 – 8

€ 110 per night
Guest favorite

Barn in Bolsover

4.95 out of 5 average rating, 40 reviews

Gravediggers Cottage

Sep 12 – 19

€ 128 per night
Guest favorite

Home in Darley Dale

5.0 out of 5 average rating, 52 reviews

Spacious Scandinavian style hideaway with log fire

May 11 – 18

€ 214 per night

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

5.4K reviews

Nightly prices starting at

€ 19 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 house rentals in Chesterfield?

    Experience the best of Chesterfield with our house rentals, starting at about $30 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 160 vacation rentals in Brimington CP, and over 160 vacation rentals in Chesterfield.

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Derbyshire
  5. Chesterfield