Chesterfield Holidays

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Your Chesterfield Holiday

Book a Chesterfield holiday package and get set to experience all this lively city has to offer. Consider basing yourself in the neighbourhood of Shirland, which is good for culture, golfing and history. Make your trip to Chesterfield even more enjoyable by including some sightseeing. Bolsover Castle, Chesterfield Market and Poolsbrook Country Park are among the popular attractions you'll want to explore. Stop dreaming and start travelling. Check out the multitude of options on Expedia today and put your Chesterfield holiday plans into action!

Chesterfield Holiday

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

WILDES INNS

WILDES INNS

4 out of 5
Worksop Road, Clowne, Chesterfield, England
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,010 reviews)
Very nice hotel, however room for improvement.
"Overall the stay was very good. Reception staff were friendly and extremely helpful in sorting out an issue. The bar/restaurant staff equally as friendly and helpful sorting out a couple of requests. The bar prices did seem quite excessive though. It’s actually slightly cheaper in central London ..."

Reviewed on 29 Jul. 2025

Get rates
WILDES INNS
Ringwood Hall Hotel & Spa

Ringwood Hall Hotel & Spa

4 out of 5
Chesterfield Road, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is AU$155 per night from 25 Aug to 26 Aug
AU$155
25 Aug - 26 Aug
includes taxes & fees
8/10 Very Good! (919 reviews)
"Lovely hotel in Chesterfield. Very comfortable room, even though furnishings etc were quite dated. Hotel itself full of character and staff very friendly and efficient. Lovely to have breakfast included! Would love to stay again and next time try the spa!"

Reviewed on 29 Jul. 2025

Ringwood Hall Hotel & Spa
Radisson Blu Hotel, Sheffield

Radisson Blu Hotel, Sheffield

4 out of 5
Pinstone Street, 30, Sheffield, England
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 17 Aug to 18 Aug
AU$173
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (398 reviews)
"The property was luxurious, very convenient for ponds forge and very amenable"

Reviewed on 30 Jul. 2025

Radisson Blu Hotel, Sheffield
See all 5,165 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.
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Discover the most popular places to visit in Chesterfield

Bolsover Castle

You can find out about the history of Bolsover with a stop at Bolsover Castle. Visit the spas and lively bars in this relaxing area.

Bolsover Castle

Barrow Hill Roundhouse Railway Centre

You can spend an afternoon browsing the exhibits at Barrow Hill Roundhouse Railway Centre in Brimington. Make time to visit the area's spas or simply enjoy its lively bars.

Barrow Hill Roundhouse Railway Centre

Poolsbrook Country Park

Explore the great outdoors at Poolsbrook Country Park, a lovely green space in Staveley. Visit the spas and top-notch restaurants in this relaxing area.

Poolsbrook Country Park

What to do in Chesterfield

eSIM: Airalo Europe Package - United Kingdom

eSIM: Airalo Europe Package - United Kingdom

AU$5
per traveller
eSIM: Airalo Europe Package - United Kingdom
Small-Group Derbyshire, the Peak District & Poole's Cavern

Idyllic England: Derbyshire & the Peak District from Manchester

AU$145
per adult
84% of travellers recommend
Idyllic England: Derbyshire & the Peak District from Manchester
Private Shopping Tour from Sheffield to Outlet East Midlands

Private Shopping Tour from Sheffield to Outlet East Midlands

AU$197
per adult
Private Shopping Tour from Sheffield to Outlet East Midlands
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Chesterfield costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chesterfield?
If you're hoping to snag a cheap Chesterfield holiday package, consider travelling in January, April and September. You'll generally find better prices on flights and accommodation during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Chesterfield?
Dedicate at least 2 days for your Chesterfield holiday in order to enjoy everything that makes this destination special. Stroll around popular areas, including Spital and Hasland. Then check out top sights like Pomegranate Theatre and Chesterfield Museum & Art Gallery. With a well-organised itinerary, you can keep busy with room for some rest time too. Want to travel outside of Chesterfield? Consider an excursion or two.
Is it worth booking a holiday package to Chesterfield?
Chesterfield has all the ingredients you need for an amazing getaway — cycling, views and walking trails are just the start. Whether you want to visit attractions such as Barrow Hill Roundhouse Railway Centre and Queen's Park, or take the road less traveled, there's plenty to experience on your Chesterfield holiday.
How to find the best Chesterfield package deals?
Landing a cheap Chesterfield package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Chesterfield package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Chesterfield holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can customise your Chesterfield getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Chesterfield?
Enjoy amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Chesterfield adventure.
How to plan a trip to Chesterfield?

  1. Pick your dates: The things you plan to do in Chesterfield and your favourite season can help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and experiences. Your hotel will probably be the biggest expense during your trip to Chesterfield.
  3. Determine how many days away: Start by compiling a list of the attractions you'd like to get to in Chesterfield. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodation and airfare: After you've settled on your dates and duration, lock in the ideal Chesterfield holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.