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.
Recommended holiday lettings in Chesterfield
Rent a holiday home, apartment or cottage in Chesterfield from just £41 per night
Holiday lettings and apartments with air conditioning
Best holiday rentals with a balcony
Most popular holiday lettings with a fireplace
Best holiday rental deals in Chesterfield
Save up to 27%
Discover a letting that meets your needs among the 266 unique options from more than 12 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 29%.
Budget-friendly Holiday Homes in Chesterfield
Find Fantastic yet Cheap Lettings
Top-Rated Lettings and Properties in Chesterfield
Book Holiday Letting Offers with the Highest User Rating
Why choose HomeToGo?
Securely pay and stay your way
Choose local, trusted payment methods, plus trip insurance and add-on services.
Award-winning customer service
Experience seamless, hands-on support for any booking questions or concerns.
Verified reviews
Trust in the quality and comfort of your stay with verified guest reviews.
Price clarity, no surprises
Spend your budget exactly as planned by comparing thousands of providers.
Smart search made simple
Transform holiday planning into a joy with advanced, AI-powered search tools.
Find your dream stay
Explore 15 million+ rentals, the world’s biggest selection of holiday homes.
Popular holiday rental amenities in Chesterfield
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.
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 | 266 rentals |
|---|---|
| 💳 Discounts available | up to 29% |
| 🌙 Nightly prices from | £41 |
| ⭐ Popular amenities | Pets allowed, Pool and Parking |
| 🐾 Pet friendly rentals | 68 properties |
Frequently Asked Questions
What is a common nightly price for a holiday home in Chesterfield?
The average price per night in Chesterfield is around £41. The nightly rate for cottage is £226 on average. House rentals costs around £269 per night.
How many holiday lettings are available to book in Chesterfield?
Currently there are 266 holiday lettings from 12 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 68 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 £41 - 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 29%. 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 266 offers from 12 providers in the region, you're sure to find the right type of accommodation with the amenities and features you need in Chesterfield.
We list offers from thousands of providers, including
Top cities to visit
- Accommodation & Holiday Apartments in Liverpool
- Accommodation & Holiday Homes in Brighton
- Accommodation in Belfast
- Holiday Cottages & Accommodation in Aviemore
- Accommodation & Holiday Cottages in Chester
- Holiday Accommodation & Rooms in Oxford
- Accommodation in Coventry
- Holiday Homes in Pitlochry
- Holiday Cottages & Accommodation in Fort William
- Accommodation in Sheffield
- Accommodation in Minehead
- Accommodation in Portrush
- Holiday Homes in Dundee
- Cottages in Carbis Bay
- Holiday Cottages & Accommodation in Ambleside
Top holiday ideas
Find holiday inspiration for your next trip
- Holiday Parks in Newquay
- Dog-Friendly Holidays in Lake District
- B'n'Bs in Chelmsford
- Golf Breaks in St Andrews
- Bude Holiday Cottages
- B'n'Bs in Clacton-on-Sea
- Blakeney Holiday Cottages
- B'n'Bs in Broughty Ferry
- B'n'Bs in Carbis Bay
- B'n'Bs in Truro
- Holiday Parks in Camber
- B'n'Bs in Keswick
- Weekend Breaks in Newcastle
- Cottages & Lodges with Hot Tubs in the Lake District
- B'n'Bs in Reading
- Dog-Friendly Holidays in Dorset
- Holiday Homes with Hot Tubs in Derbyshire
- Weekend Breaks in Suffolk
- B'n'Bs in Sidmouth
- B'n'Bs in Hemel Hempstead
- Weekend Breaks in West Wales