Chesterfield Holidays from £202

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Your Chesterfield Holiday

A great way to experience this exciting city is with a tailor-made Chesterfield holiday package. Base yourself in the neighbourhood of Shirland, which is good for culture, golfing and history or go someplace else — our packages are all about you. Eager to start exploring your surroundings? Bolsover Castle, Chesterfield Market and Barrow Hill Roundhouse Railway Centre are just three of the best places to visit during a trip to Chesterfield. Stop daydreaming and start adventuring. Browse the broad range of options on Expedia today and finally put your Chesterfield holiday plans into motion!

The Latest Chesterfield Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Alan

The Alan

4 out of 5
Manchester City Centre
per person
22 Sept - 25 Sept
found 1 day ago
Return flight included
London (LON) to Manchester (MAN)
8.6/10 Excellent! (1,003 reviews)
I had a great stay and would stay again and also recommend to others. Easy to get around, my stay was based on attending the Albert Hall which was literally less than a 10min walk.

Reviewed on 29 Jun 2025

Treehouse Hotel Manchester

Treehouse Hotel Manchester

4 out of 5
Manchester City Centre
per person
16 Aug - 18 Aug
found 5 hours ago
Return flight included
Belfast (BFS) to Manchester (MAN)
9.6/10 Exceptional! (110 reviews)
Staff were great especially Lucy in the restaurant. Hotel is a gem. Breakfast was delicious and gym is nice and big with lots of equipment. Only negative was the service charge on the bill. I hope this isn't going to bleed into the hotel sector so owners can pay their staff less. I paid this time but definitely will not pay again.

Reviewed on 26 Jun 2025

Sweet Suites Lytham St Annes

Sweet Suites Lytham St Annes

4 out of 5
Save 100% on your flight
per person
6 Sept - 13 Sept
found 5 hours ago
Return flight included
London (LON) to Manchester (MAN)
9.8/10 Exceptional! (119 reviews)
Nicest stay in Lytham, quiet and super clean. Friendly staff.

Reviewed on 14 May 2025

Oyo A Better Night Hotel Limited

Oyo A Better Night Hotel Limited

3 out of 5
per person
16 Aug - 18 Aug
found 5 hours ago
Return flight included
Belfast (BFS) to Manchester (MAN)
8.6/10 Excellent! (59 reviews)
Room size was good. Receptionist was very kind. Free car parking space added extra value of stay. Hot water shower was quick and comfort water pressure. Only drawback is cleanliness. Toilet seat rim has yellow stains. And there was not toilet roll in the room but paper handkerchief box helped a bit. Recommend if travellers seeking good value stay near salford

Reviewed on 21 Jun 2025

Aston Court Derby City Centre by Belvilla

Aston Court Derby City Centre by Belvilla

3 out of 5
per person
19 Aug - 24 Aug
found 1 day ago
Return flight included
London (LHR) to Manchester (MAN)
8/10 Very Good! (606 reviews)
I booked two rooms, one with a double bed and one with two singles. We were given two rooms each with two single beds. One room was too small. Our rooms were on the third floor without lift. Was hard to go up and down so many steps.

Reviewed on 29 Jun 2025

Velvet Hotel Manchester, WorldHotels Crafted

Velvet Hotel Manchester, WorldHotels Crafted

4 out of 5
Manchester City Centre
per person
22 Sept - 25 Sept
found 1 day ago
Return flight included
London (LON) to Manchester (MAN)
9/10 Wonderful! (1,004 reviews)
Quick check in, close to train station and bars

Reviewed on 21 Jun 2025

Chesterfield Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
East Midlands Airport (EMA)
Population
113,100
Max Temp Winter
7ºC
Max Temp Summer
18ºC
Top Sights
Bolsover Castle, Hotel Van Dyk Theatre and Barrow Hill Roundhouse Railway Centre

Our pick of the best Chesterfield Hotel Deals

Casa Hotel
Casa Hotel
4 out of 5
Lockoford Lane, Chesterfield, England
Stay at this 4-star business-friendly hotel in Chesterfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the ...
9.4/10 Exceptional! (1,003 reviews)
"Great hotel with easy access to Peak District. Free parking available."

Reviewed on 27 Jun 2025

Casa Hotel
Ringwood Hall Hotel & Spa
Ringwood Hall Hotel & Spa
4 out of 5
Chesterfield Road, Chesterfield, England
Stay at this spa hotel in Chesterfield. Enjoy free Wi-Fi, a full-service spa and 24-hour room service. Our guests praise the helpful staff and the property condition ...
8/10 Very Good! (900 reviews)

Reviewed on 24 Jun 2025

Ringwood Hall Hotel & Spa
WILDES INNS
WILDES INNS
4 out of 5
Worksop Road, Clowne, Chesterfield, England
Stay at this 4-star business-friendly hotel in Chesterfield. Enjoy free Wi-Fi, free parking and room service. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,003 reviews)
"Really nice hotel, very clean and new, however it was bit pricey in the bar and restaurant, although had a nice meal. All good.."

Reviewed on 30 Jun 2025

WILDES INNS
See all 5,279 properties in Chesterfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Chesterfield holiday with Expedia?
With exceptional-value airfares, hotel and car hire options all in one place, Expedia makes arranging your Chesterfield getaway a cinch. Plus, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Choose from fantastic properties, add flights and/or a hire car (and maybe also some exciting activities!) and get incredible prices. Need to change your plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, head over to our Customer Service Portal link.
When is the best time of year to holiday in Chesterfield?
Love sightseeing but don't like crowds? Lock in your Chesterfield getaway for May, July and December. Typically, it's a lot quieter than in February, March and June. Organise your trip to Chesterfield according to what type of holiday you're looking for. January is the coolest time of year, when average daytime temperatures are 3ºC. In July, the warmest month, you'll experience averages of 16ºC during the day.
What are the top hotels for my holiday in Chesterfield?
Many visitors to Chesterfield often stay in Tupton. ibis Chesterfield North - Barlborough and ibis Chesterfield Centre -- Market Town are popular options in this neighbourhood. But it's not the only exciting place in town! Wingerworth is another fantastic area and where you'll find Van Dyk by Wildes and Casa Hotel.
How do I get a cheap holiday to Chesterfield?
Bundle your bookings with Expedia to save on your next getaway. With over 400 partner airlines and 321,000 hotels across the globe, your Chesterfield holiday can be tailored exactly to suit your budget. With all those extra pounds, why not throw in a few awesome activities and tours? It's an easy way to unlock even more bargains. Your dream getaway to Chesterfield is closer than you thought! Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Chesterfield holiday?
There are lots of places to check out while on your holiday in Chesterfield. Chatsworth House, Bolsover Castle, Hardwick Hall and Chatsworth House Labyrinth are a few of this city's top attractions.
What is the best area to stay in when on holiday in Chesterfield?
If you plan to check out Bolsover Castle, save yourself the hassle of commuting and lock in a stay nearby. It's one of the best attractions in Chesterfield.
Do I need a visa for my Chesterfield holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and reason for your visit, whether it be for tourism or work, will determine if you'll need a visa for Chesterfield. Also double-check that your passport is up to date and has a minimum of six months validity remaining beyond the date of your return. Finalise all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Chesterfield holiday?
Do some research into the types of clothing people in Chesterfield wear, and consider browsing social media fashion pages for inspiration. You'll want to create a versatile wardrobe with pieces that work for your destination and showcase your unique style. Pack your luggage with confidence by checking the local weather conditions in Chesterfield. July brings the warmest temperatures, with daytime averages of 16ºC, while January days average 3ºC, making it the coolest month.
What does an Expedia Chesterfield holiday include?
Expedia has everything you need to plan your Chesterfield getaway, but how your package is structured is up to you. Choose from any combination of flights, hotels and hire cars. Looking for some activities or tours to fill in your time? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a holiday package to suit your needs. Discover a wide range of property types and pick one that fits your group size and travel needs. The most in-demand holiday rentals here are cottages and private holiday homes. With Expedia, it's easy to tailor your Chesterfield retreat just the way you like.
Does Expedia offer Book Now, Pay Later Chesterfield holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's easy instalment plans. If paying just a small amount each month sounds right for you, choose this option during the checkout process.
  • No-deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.

Can I choose my airline with a Chesterfield Expedia holiday?
Yes, and with over 400 airlines to select from worldwide, you're not short on choice. Have a look through the available options and see which airline best fits your budget and needs.

Discover the most popular places to visit in Chesterfield

Hardwick Hall

Hardwick Hall

5/5(20 reviews)

You can find out about the history of Chesterfield when you stop by Hardwick Hall. Visit the lively bars or top-notch restaurants in this relaxing area.

Hardwick Hall
Mecca Bingo

Mecca Bingo

Why not try your luck with a visit to Mecca Bingo during your visit to Chesterfield? Visit the spas and top-notch restaurants in this family-friendly area.

Mecca Bingo

Bolsover Castle

5/5(1 review)

You can find out about the history of Bolsover with a stop at Bolsover Castle. Visit the spas and top-notch restaurants in this relaxing area.

Bolsover Castle

Unmissable things to do in Chesterfield

Small-Group Derbyshire, the Peak District & Poole's Cavern

Idyllic England: Derbyshire & the Peak District from Manchester

£71
per adult
84% of travellers recommend
Idyllic England: Derbyshire & the Peak District from Manchester
7 Hours Pub Tours in Peak District

7 Hours Pub Tours in Peak District

£125
per adult
7 Hours Pub Tours in Peak District
VIP Queue Jumps in Bournemouth

Bar and Club entry Night Pass to multiple venues in Sheffield

£10
per adult
Bar and Club entry Night Pass to multiple venues in Sheffield
See all activities in Chesterfield

The Advantages of Chesterfield Weekend Breaks

Discover a different side of the British Isles with a weekend break in Chesterfield. Take short breaks away from home and enjoy some quality time in a beautiful place. You’ll come back feeling refreshed and inspired. You can have an action-packed Chesterfield weekend break or get some peace with a relaxing holiday. Whatever experience you’re looking for, find it with our deals on hotels in Chesterfield.

Cheap Weekend Breaks to Chesterfield

There are lots of ways to take cheap weekend breaks to Chesterfield. Expedia offers deals on car hires and hotel rooms and covers trips for all kinds of travellers. The best way to save is with our holiday packages in Chesterfield. First, choose your car hire and hotel reservation. Then we’ll bundle them together into one discounted price. Solo explorers, couples, families, and groups of friends can discover budget solutions for their weekend breaks. Once you arrive, enjoy some of the fun things to do, many of which are free or cheap to experience  

Chesterfield Romantic Weekend Breaks

Couples love taking romantic weekend breaks in Chesterfield. Whisking your lover away for a romantic Chesterfield weekend break is the perfect opportunity to make new memories together. Expedia offers all kinds of hotel options, so you can find romantic hotels in Chesterfield and choose the best place for you. Check out our deals on beautiful properties, and you’ll save even more when you choose to package your hotel reservation with a car hire.

Family Weekend Breaks in Chesterfield

Set some time aside to experience family weekend breaks in Chesterfield. There are plenty of excellent family-friendly hotels in Chesterfield within our selection of hotels. You can also find a place to call home in one of the holiday rentals in Chesterfield. With accommodation, activities, and adventure all waiting, there’s never been a better time to plan Chesterfield family weekend breaks.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.