Chesterfield District holiday homes and accommodation - HomeToGo base64Hash Chesterfield District holiday homes and accommodation - HomeToGo

Chesterfield District holiday homes and accommodation

Find 291 available offers from 11 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended holiday lettings in Chesterfield

Find your perfect holiday home, apartment or cottage in Chesterfield from just £52 per night!

Accommodation Chesterfield District
26 Apr - 3 May
Accommodation ∙ 15 guests ∙ 1 bedroom

Beautiful letting with garden & terrace | Suitable for remote work

Chesterfield District, Derbyshire, United Kingdom
£1,012
per night
HomeToGo
£1,012
per night
View deal
HomeToGo
Cottage Chesterfield District
-65%
28 Mar - 4 Apr
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage with garden

Chesterfield District, Derbyshire, United Kingdom
£168£58
per night
Very good(8 ratings)
HomeToGo
£168£58
per night
View deal
HomeToGo
Apartment Chesterfield District
28 Mar - 4 Apr
Apartment ∙ 4 guests ∙ 2 bedrooms

Charming apartment with 2 rooms for 4 persons

Chesterfield District, Derbyshire, United Kingdom
£71
per night
Vrbo
£71
per night
View deal
Vrbo
Cottage Chesterfield District
-24%
21 Mar - 28 Mar
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage with terrace, garden & hot tub | Nature view

Chesterfield District, Derbyshire, United Kingdom
£295£225
per night
Outstanding(30 ratings)
Vrbo
£295£225
per night
View deal
Vrbo
House Chesterfield District
22 Mar - 29 Mar
House ∙ 5 guests ∙ 2 bedrooms

Holiday home | Dogs allowed

Chesterfield District, Derbyshire, United Kingdom
£82
per night
HousingAnywhere
£82
per night
View deal
HousingAnywhere
Cottage Chesterfield District
15 Nov - 22 Nov
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage with garden

Chesterfield District, Derbyshire, United Kingdom
£66
per night
Outstanding(69 ratings)
HomeToGo
£66
per night
View deal
HomeToGo
Cottage Chesterfield District
-24%
28 Mar - 4 Apr
Cottage ∙ 6 guests ∙ 1 bedroom

Fully equipped cottage with terrace & garden | Pets allowed

Chesterfield District, Derbyshire, United Kingdom
£295£225
per night
HomeToGo
£295£225
per night
View deal
HomeToGo
House Chesterfield District
26 Apr - 3 May
House ∙ 16 guests ∙ 1 bedroom

Holiday home for 16 persons

Chesterfield District, Derbyshire, United Kingdom
£374
per night
HomeToGo
£374
per night
View deal
HomeToGo
House Chesterfield District
26 Apr - 3 May
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with terrace | Nature view

Chesterfield District, Derbyshire, United Kingdom
£164
per night
Vrbo
£164
per night
View deal
Vrbo
House Chesterfield District
26 Apr - 3 May
House ∙ 15 guests ∙ 1 bedroom

Holiday home with garden

Chesterfield District, Derbyshire, United Kingdom
£250
per night
HomeToGo
£250
per night
View deal
HomeToGo
Accommodation Chesterfield District
26 Apr - 3 May
Accommodation ∙ 12 guests ∙ 1 bedroom

Wonderful letting with garden | Perfect for remote work

Chesterfield District, Derbyshire, United Kingdom
£264
per night
HomeToGo
£264
per night
View deal
HomeToGo
Apartment Chesterfield District
28 Mar - 4 Apr
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment | Perfect for remote work

Chesterfield District, Derbyshire, United Kingdom
£145
per night
Outstanding(2 ratings)
Vrbo
£145
per night
View deal
Vrbo
Accommodation Chesterfield District
26 Apr - 3 May
Accommodation ∙ 15 guests ∙ 1 bedroom

Letting with garden & terrace

Chesterfield District, Derbyshire, United Kingdom
£120
per night
HomeToGo
£120
per night
View deal
HomeToGo
Cottage Chesterfield District
-60%
28 Mar - 4 Apr
Cottage ∙ 6 guests ∙ 4 bedrooms

Cottage with garden

Chesterfield District, Derbyshire, United Kingdom
£149£61
per night
Outstanding(2 ratings)
Vrbo
£149£61
per night
View deal
Vrbo
House Chesterfield District
24 May - 31 May
House ∙ 4 guests ∙ 2 bedrooms

Holiday home with garden

Chesterfield District, Derbyshire, United Kingdom
£100
per night
Vrbo
£100
per night
View deal
Vrbo

Best holiday lettings with a pool

Cottage  Chesterfield District
4 Apr - 11 Apr
£97 per night
Cottage ∙ 8 guests ∙ 3 bedrooms

Family-friendly pleasant cottage with garden & pool | Pet-friendly

4.9
Outstanding(8 ratings)
Chesterfield District, Derbyshire, United Kingdom
Pool
HomeToGo
View deal
Cottage  Chesterfield District
9 May - 16 May
-32%
£184
£125 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage with garden, terrace & BBQ | Golf view

5.0
Outstanding(31 ratings)
Chesterfield District, Derbyshire, United Kingdom
Pool
HomeToGo
View deal
Cottage  Chesterfield District
18 Apr - 25 Apr
-26%
£184
£137 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage with pool, garden & barbecue

5.0
Outstanding(31 ratings)
Chesterfield District, Derbyshire, United Kingdom
Pool
Vrbo
View deal
See all offers

Top holiday lettings with fishing spots nearby

Cottage  Chesterfield District
14 Sept - 21 Sept
-33%
£113
£76 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Children-friendly cottage with garden & terrace | Pets are welcome

4.5
Excellent(51 ratings)
Chesterfield District, Derbyshire, United Kingdom
Fishing
HomeToGo
View deal
Cottage  Chesterfield District
27 Jun - 4 Jul
-42%
£283
£164 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Children-friendly pleasant cottage with barbeque, terrace & garden | Pets allowed

4.9
Outstanding(39 ratings)
Chesterfield District, Derbyshire, United Kingdom
Fishing
Vrbo
View deal
Cottage  Chesterfield District
20 Sept - 27 Sept
-43%
£198
£112 per night
Cottage ∙ 6 guests ∙ 4 bedrooms

Cottage with garden

Chesterfield District, Derbyshire, United Kingdom
Fishing
Vrbo
View deal
See all offers

Best holiday rental deals in Chesterfield

Save up to 62%

Cottage Chesterfield District
11 Apr - 18 Apr
-62%
£137
£52 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Family-friendly lovely cottage with barbecue & garden

4.3
Very good(10 ratings)
Chesterfield District, Derbyshire, United Kingdom
HomeToGo
View deal
Cottage Chesterfield District
13 Mar - 20 Mar
-19%
£251
£204 per night
Cottage ∙ 12 guests ∙ 5 bedrooms

Cottage with garden

4.9
Outstanding(21 ratings)
Chesterfield District, Derbyshire, United Kingdom
HomeToGo
View deal
Cottage Chesterfield District
5 Sept - 12 Sept
-27%
£127
£94 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Children-friendly cottage with terrace, garden & barbeque

5.0
Outstanding(28 ratings)
Chesterfield District, Derbyshire, United Kingdom
HomeToGo
View deal

Discover a letting that meets your needs among the 291 unique options from more than 10 providers in Chesterfield District. HomeToGo allows you to instantly compare the offers for each property from numerous partner websites to find the best price and save up to 28%.

Budget-friendly Holiday Homes in Chesterfield

Find Fantastic yet Cheap Lettings

House Chesterfield District
28 Mar - 4 Apr
£133 per night
House ∙ 14 guests ∙ 6 bedrooms

House with garden | Good for workation

Chesterfield District, Derbyshire, United Kingdom
Vrbo
View deal
Cottage Chesterfield District
12 Sept - 19 Sept
-36%
£113
£73 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Family-oriented cottage with garden | Golf view

4.8
Outstanding(38 ratings)
Chesterfield District, Derbyshire, United Kingdom
HomeToGo
View deal
Cottage Chesterfield District
27 Jun - 4 Jul
£78 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Child-friendly cottage with terrace & garden | Golf view

Chesterfield District, Derbyshire, United Kingdom
HomeToGo
View deal

Top-Rated Lettings and Properties in Chesterfield

Book Holiday Letting Offers with the Highest User Rating

House Chesterfield District
4 Oct - 11 Oct
-8%
£142
£130 per night
House ∙ 4 guests ∙ 2 bedrooms

Family-oriented lovely holiday home with garden & barbecue | City view | Dogs allowed

5.0
Outstanding(59 ratings)
Chesterfield District, Derbyshire, United Kingdom
Vrbo
View deal
Cottage Chesterfield District
29 Aug - 5 Sept
-43%
£349
£199 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

Children-friendly nice cottage with garden & barbecue | Golf view

5.0
Outstanding(50 ratings)
Chesterfield District, Derbyshire, United Kingdom
HomeToGo
View deal
Cottage Chesterfield District
12 Sept - 19 Sept
-36%
£113
£73 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Fully equipped cottage with garden

4.8
Outstanding(38 ratings)
Chesterfield District, Derbyshire, United Kingdom
Vrbo
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Chesterfield

  • Pet-friendly (76)
  • Pool (4)
  • Parking (4)
  • WiFi (245)
  • Fireplace (35)
  • Hot tub (21)
  • TV (208)
  • Kitchen (204)
  • Balcony/patio (56)
  • Washing machine (161)
  • Garden (141)
  • No smoking (212)

Travellers who are looking for a pet-friendly accommodation will find Chesterfield District convenient, since many rentals are pet-friendly. If this is a top requirement for you, check the hotel room in Chesterfield District. This is the most pet-friendly accommodation type there. If you want to stay central, a few of the pet-friendly holiday lettings are less than 2 kilometres away from the city centre.

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.

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.

Information about holiday rentals in Chesterfield

🏡 Holiday homes available 291 rentals
💳 Discounts available up to 28%
🌙 Nightly prices from £52
⭐ Popular amenities Pets allowed, Pool and Parking
🐾 Pet friendly rentals 76 properties
38,467 reviews
Chesterfield District holiday rentals have an average rating of 4.3/5 across 38,467 reviews left by travellers.

Frequently Asked Questions

What is a common nightly price for a holiday home in Chesterfield?

The average price per night in Chesterfield is around £52. The nightly rate for cottage is £236 on average. House rentals costs around £370 per night.

How many holiday lettings are available to book in Chesterfield?

Currently there are 291 holiday lettings from 10 different providers on offer in Chesterfield.

What is the most popular holiday home amenity in Chesterfield?

Travellers planning trips to Chesterfield District usually search for Pets allowed, Pool, and Parking when it comes to holiday rental amenities.

Am I allowed to bring my pet during my stay in an accommodation in Chesterfield?

Pets are welcome in Chesterfield with 76 pet-friendly holiday rentals.

What is the best time of year to travel to Chesterfield District?

Sun lovers should visit Chesterfield District in July and August to enjoy the warmest weather.

Where can I see discounts on holiday accommmodation in Chesterfield?

You can get brilliant bargains on holiday accommodation in Chesterfield with the nightly price of a rental starting at just £52 - and HomeToGo has launched plenty of filters that make it a piece of cake to locate the best offers. When considering different dates for your holiday, try a search using HomeToGo's flexible dates technology to easily look for lower cost timings and get savings of up to 28%. Moreover, HomeToGo's 'distance from' filter lets you see hidden treasure holiday rentals in lower-price, lesser-known spots that are just as close to the area of your choice, whether that's the coastline, a swimming lake, winter sports area or town centre. Book early to make the most of the greatest variety of options and the best deals - and do so free from stress by clicking on HomeToGo's 'free cancellation' filter as you look for the perfect holiday home.

What are the pros of booking a holiday letting in Chesterfield with HomeToGo?

From serenity away from the crowds to plenty of room in which to have fun with your family, friends or partner, holiday homes in Chesterfield bring plenty of advantages. HomeToGo provides genuine ratings from verified visitors, and searching is safe, easy, and hassle-free - so with 291 offers from 10 providers in the region, you're sure to find the right type of accommodation with the amenities and features you need in Chesterfield.

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