Holiday lettings & accommodation in Chesterfield - HomeToGo base64Hash Holiday lettings & accommodation in Chesterfield - HomeToGo

Holiday lettings & accommodation in Chesterfield

Find 208 available offers from 11 partners
Chesterfield District
Anytime
Guests
Chesterfield District
Anytime
Guests

Popular Filters to discover the perfect holiday home in Chesterfield

House
2 Adults
Pets allowed
Hot tub
Pool
Cottage
Cabin

Discover quaint local charm with a holiday cottage in Chesterfield

Choose from a range of accommodation options; from rustic farmhouses in the surrounding countryside to chic apartments in the heart of the town. Whether you're travelling solo or with the family, a holiday letting will help you make the most of your time in Chesterfield.

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Recommended pet-friendly holiday lettings

Bringing a canine companion along on your travels? Whether they're exploring the surroundings or finding a spot in which to snuggle up on the sofa, your pet will be welcome at one of the 30 dog-friendly holiday lettings in Chesterfield.

Cottage  Chesterfield District
29 Jun - 6 Jul
£104 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Pleasant Cottage in Old Whittington with Private Parking + Amazing Views

Chesterfield District, Derbyshire, United Kingdom
Pet-friendly
Details
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Cottage  Chesterfield District
2 Nov - 9 Nov
-68%
£205
£66 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Hollingwood with Spacious Garden

Chesterfield District, Derbyshire, United Kingdom
Pet-friendly
Details
HomeToGo
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Cottage  Chesterfield District
1 Jun - 8 Jun
-30%
£128
£90 per night
Cottage ∙ 5 guests ∙ 3 bedrooms

Cottage in Inkersall with Private Parking + Panoramic Views

Chesterfield District, Derbyshire, United Kingdom
Pet-friendly
Details
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Best holiday rentals with a balcony

Want to see even more of Chesterfield District on your trip? Enjoy incredible views across this destination from your holiday home or apartment by booking a rental with a balcony in Chesterfield.

House  Chesterfield District
8 Jun - 15 Jun
-30%
£158
£110 per night
House ∙ 4 guests ∙ 3 bedrooms

Wonderful Holiday Home in New Whittington with Garden

Chesterfield District, Derbyshire, United Kingdom
Balcony
Details
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House  Chesterfield District
22 Jun - 29 Jun
£252 per night
House ∙ 14 guests ∙ 5 bedrooms

House in Old Whittington with Garden

Chesterfield District, Derbyshire, United Kingdom
Balcony
Details
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House  Chesterfield District
9 Sept - 16 Sept
£221 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Chesterfield with Terrace, Barbecue, Hot Tub

Chesterfield District, Derbyshire, United Kingdom
Free cancellation
Balcony
Details
Agoda
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Best holiday lettings with a pool

A swimming pool is a holiday home staple, and with 0% of the holiday rentals in Chesterfield providing pool access, there are plenty of great options from which to choose. Get ready to take a dip and dive into the top offers for accommodation with private pools in Chesterfield.

House  Chesterfield District
12 Oct - 19 Oct
£2,333 per night
House ∙ 23 guests ∙ 6 bedrooms

Wonderful House in Aughton with Hot Tub, Garden & Barbecue

4.5
Excellent (3 ratings)
Chesterfield District, Derbyshire, United Kingdom
Free cancellation
Pool
Details
HomeToGo
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Cottage  Chesterfield District
28 Sept - 5 Oct
-26%
£107
£80 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Charming Cottage in Sheffield with Private Parking

Chesterfield District, Derbyshire, United Kingdom
Pool
Details
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Cottage  Chesterfield District
8 Nov - 15 Nov
-51%
£192
£94 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Grindleford with Private Parking

5.0
Outstanding (12 ratings)
Chesterfield District, Derbyshire, United Kingdom
Pool
Details
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Best holiday rental deals in Chesterfield

Save up to 67%

House Chesterfield District
1 Feb - 8 Feb
-22%
£109
£85 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday Home in Chesterfield with Garden

Chesterfield District, Derbyshire, United Kingdom
Free cancellation
Details
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Cottage Chesterfield District
25 Jan - 1 Feb
-67%
£321
£105 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

Pleasant Cottage in Chesterfield with Garden

Chesterfield District, Derbyshire, United Kingdom
Details
HomeToGo
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House Chesterfield District
23 Nov - 30 Nov
-28%
£129
£93 per night
House ∙ 4 guests ∙ 2 bedrooms

Nice Holiday Home in Chesterfield with Garden

4.0
Very good (31 ratings)
Chesterfield District, Derbyshire, United Kingdom
Free cancellation
Details
HomeToGo
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You can choose from 208 great holiday lettings from 11 providers in Chesterfield District, with nightly prices beginning at £60. HomeToGo instantly presents you with the best offers by comparing the listed properties.

Recommended holiday lettings in Chesterfield

Rent a holiday home, apartment or cottage in Chesterfield from just £51 per night

Cottage Chesterfield District
9 Nov - 16 Nov
-73%
£256
£68 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Barrow Hill with Garden

4.8
Outstanding (7 ratings)
Chesterfield District, Derbyshire, United Kingdom
Details
HomeToGo
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Cottage Chesterfield District
8 Jun - 15 Jun
-39%
£127
£77 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Barrow Hill with Garden

4.8
Outstanding (7 ratings)
Chesterfield District, Derbyshire, United Kingdom
Details
HomeToGo
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House Chesterfield District
30 Aug - 6 Sept
£89 per night
House ∙ 6 guests ∙ 3 bedrooms

Wonderful House in Chesterfield with Private Garden + Church View

4.8
Outstanding (45 ratings)
Chesterfield District, Derbyshire, United Kingdom
Details
HolidayLettings
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House Chesterfield District
25 Oct - 1 Nov
-23%
£131
£101 per night
House ∙ 4 guests ∙ 2 bedrooms

Pleasant House in Chesterfield with Off-Site Parking

4.8
Outstanding (16 ratings)
Chesterfield District, Derbyshire, United Kingdom
Details
Vrbo
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House Chesterfield District
10 Aug - 17 Aug
£100 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday Home in Chesterfield with Free Parking

Chesterfield District, Derbyshire, United Kingdom
Details
Vrbo
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House Chesterfield District
8 Jun - 15 Jun
£95 per night
House ∙ 4 guests ∙ 2 bedrooms

Large Holiday Home in Chesterfield with Terrace & Garden

4.0
Very good (2 ratings)
Chesterfield District, Derbyshire, United Kingdom
Details
Vrbo
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House Chesterfield District
25 May - 1 Jun
£82 per night
House ∙ 5 guests ∙ 2 bedrooms

Holiday Home in Chesterfield

Chesterfield District, Derbyshire, United Kingdom
Details
HousingAnywhere
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House Chesterfield District
24 Aug - 31 Aug
£1,411 per night
House ∙ 20 guests ∙ 7 bedrooms

House in Chesterfield with Sauna, Hot Tub & Garden

5.0
Outstanding (1 rating)
Chesterfield District, Derbyshire, United Kingdom
Free cancellation
Details
HomeToGo
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Cottage Chesterfield District
8 Nov - 15 Nov
-77%
£1,139
£268 per night
Cottage ∙ 10 guests ∙ 5 bedrooms

Cottage in Hasland with Garden, Hot Tub

5.0
Outstanding (19 ratings)
Chesterfield District, Derbyshire, United Kingdom
Details
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Budget-friendly Holiday Homes in Chesterfield

Find Fantastic yet Cheap Lettings

House Chesterfield District
9 Jun - 16 Jun
£192 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday Home in Chesterfield with Garden

Chesterfield District, Derbyshire, United Kingdom
Details
HolidayLettings
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House Chesterfield District
16 Nov - 23 Nov
-29%
£141
£101 per night
House ∙ 6 guests ∙ 2 bedrooms

Holiday Home in Spital

Chesterfield District, Derbyshire, United Kingdom
Free cancellation
Details
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House Chesterfield District
26 Sept - 3 Oct
£93 per night
House ∙ 4 guests ∙ 2 bedrooms

Beautiful Holiday Home in Chesterfield with Free Parking

3.0
(1 rating)
Chesterfield District, Derbyshire, United Kingdom
Details
Vrbo
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Top-Rated Lettings and Properties in Chesterfield

Book Holiday Letting Offers with the Highest User Rating

Apartment Chesterfield District
8 Jun - 15 Jun
£161 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Entire Flat in Chesterfield

5.0
Outstanding (2 ratings)
Chesterfield District, Derbyshire, United Kingdom
Details
Vrbo
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Cottage Chesterfield District
9 Jun - 16 Jun
£127 per night
Cottage ∙ 8 guests ∙ 1 bedroom

Cottage in Barrow Hill with Garden

5.0
Outstanding (1 rating)
Chesterfield District, Derbyshire, United Kingdom
Details
Expedia
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House Chesterfield District
22 Jun - 29 Jun
£192 per night
House ∙ 6 guests ∙ 4 bedrooms

House in Chesterfield with Garden

5.0
Outstanding (1 rating)
Chesterfield District, Derbyshire, United Kingdom
Details
HolidayLettings
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Popular holiday rental amenities in Chesterfield

  • Pet-friendly (29)
  • Parking (5)
  • WiFi (191)
  • Fireplace (28)
  • Hot tub (16)
  • TV (174)
  • Kitchen (137)
  • Balcony/patio (55)
  • Washing machine (121)
  • Garden (112)
  • No smoking (184)
  • Microwave (110)

Lettings can be selected based on the amenities they offer. Above, you will find the total number of rentals that offer a particular amenity in Chesterfield District. You can easily choose a letting matching your needs in Chesterfield District if you need internet access during your holidays or you never miss an episode of your favourite show, as most lettings include Internet or TV. You could even look for lettings if you want a rental with a jacuzzi (5 rentals include Hot tub in Chesterfield District) or you want to sweat it out in a sauna (1 rentals with Sauna).

The Weather in Chesterfield

max.
Min.

16 days 16
max.
Min.

13 days 13
max.
Min.

15 days 15
max.
Min.
12°
10 days 10
max.
Min.
15°
11 days 11
max.
Min.
18°
10°
14 days 14
max.
Min.
20°
12°
15 days 15
max.
Min.
20°
13°
14 days 14
max.
Min.
17°
10°
12 days 12
max.
Min.
13°
13 days 13
max.
Min.

15 days 15
max.
Min.

14 days 14
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above are the weather conditions for Chesterfield District. July is the warmest month in Chesterfield, with average daily maximum temperatures of 20°. In contrast, the coolest month is February. The wettest month is January, while the driest month is April.

7-Day Weather Forecast in Chesterfield

Fri, 24 May
14°
13°

30%

0 h

10 km/h

Sat, 25 May
15°
13°

90%

0 h

7 km/h

Sun, 26 May
17°
16°

90%

1 h

14 km/h

Mon, 27 May
15°
14°

35%

1 h

17 km/h

Tue, 28 May
16°
11°

50%

0 h

18 km/h

Wed, 29 May
17°
16°

20%

1 h

20 km/h

Thu, 30 May
17°
16°

20%

0 h

12 km/h

Accommodation options for your holiday in Chesterfield

Holidaymakers searching for house rentals in Chesterfield District can find plenty of options to choose from, since this is the most typical holiday accommodation type there. House rentals there have an average cost of £376 a night and a median size of 114 m². Furthermore, these holiday rentals tend to be excellent for large groups, since most can accommodate 9 travellers. A cottage is the second most often seen type of accommodation in Chesterfield District. Cottage in Chesterfield District are 136 m² on average, with an average price of £240 a night.
What are the best places to discover the arts and culture of Chesterfield District?

Architecture and history: Stunning spires and stately homes

Built in the 1500s, Hardwick Hall stands majestic amid a picturesque estate. Delve back through its remarkable history with fascinating guided tours or take a stroll around the magnificent gardens. It is located just outside Chesterfield so you'll find plenty of parking.

The Crooked Spire of Chesterfield Parish Church is a cherished local icon. Situated in the centre of the town, the exquisite architecture dates back to Medieval times. Pre-book a tour to discover the secrets of this intriguing landmark from the locals.

Where are the unique attractions in Chesterfield?

The great outdoors: Idyllic canals and scenic parks

The glistening straits of the Chesterfield Canal stretch an impressive 46 miles. Relax and unwind with a leisurely stroll in the sunshine along the tow path, known affectionately as Cuckoo Way. If you're feeling more adventurous, try the 20 mile cycle from Chesterfield to Staveley through the tranquil countryside.

Holmebrook Valley Park is a rural gem, nestled on the outskirts of Chesterfield. Spread out a picnic blanket and bask in the spectacular scenery, or wander down to the lake and feed the ducks with your little ones. There's even a cosy cafe hidden in this peaceful haven.

What are the best events and festivals in Chesterfield?

Diary dates: Local traditions and musical treats

From May to early June Chesterfield embarks on the quirky ancient custom of well dressing. Lend a hand to the locals as they decorate the town's wells and springs with pictures made entirely from natural materials.

The town comes together on the 21st June for the Stainsby Festival. Enjoy an unforgettable weekend of folk music, theatre and real ale set against the breathtaking Derbyshire countryside.

Information about holiday rentals in Chesterfield

🏡 Holiday homes available 212 rentals
💳 Discounts available up to 77%
🌙 Nightly prices from £51
⭐ Popular amenities Pets allowed, Parking and Internet
🐾 Pet friendly rentals 30 properties

Frequently Asked Questions

How many holiday lettings are available to rent in Chesterfield?

June is the time of year with the highest amount of House rentals and Cottage available in Chesterfield, so you'll find plenty of great holiday deals during this month.

What is the most searched holiday home amenity in Chesterfield?

When looking for a holiday apartment in Chesterfield, consider looking for a place with Pets allowed, Parking, or Internet, which are the three most popular amenities for this destination.

Am I allowed to bring my pet during my stay in a Chesterfield District holiday letting?

Looking for accommodation in Chesterfield for you and your dog is easy with 30 pet-friendly holiday rentals available.

What's the best time of year to travel to Chesterfield District?

Book your Chesterfield District holiday in April or May to avoid a washout; these are the months with the least amount of rain.

Can you get discounts on holiday rentals in Chesterfield?

You can get fabulous discounts on holiday lets in Chesterfield with prices for a rental starting at just £51 - and HomeToGo has introduced a range of filters that make it a piece of cake to find some outstanding offers. If you don't have set dates for your break, you can use HomeToGo's flexible dates technology to quickly locate low-price time periods and get discounts of up to 77%. In addition, HomeToGo's 'distance from' filter lets you locate top quality accommodation offers in great value, lesser-known spots that are just as close to your desired destination, whether that's sand and sea, a mountain for snowboarding, or a city's urban hub. Book early to get the benefits of good availability and low prices - and do so free from stress by clicking on HomeToGo's 'free cancellation' filter when you search.

What are the pros of finding a holiday rental in Chesterfield with HomeToGo?

From increased privacy away from the crowds to more space in which to chill out with your loved ones, holiday homes in Chesterfield have a variety of advantages. HomeToGo shows you genuine ratings from verified visitors, and searching is secure, easy, and stress-free - so with 212 lettings from 11 providers in the vicinity, you're bound to discover the right type of accommodation with the amenities and features you need in Chesterfield.

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