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 Chesterfield England
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 19 Nov to 20 Nov
AU$173
19 Nov - 20 Nov
includes taxes & fees
WILDES INNS
Ringwood Hall Hotel & Spa, BW Signature Collection

Ringwood Hall Hotel & Spa, BW Signature Collection

4 out of 5
Chesterfield Road Chesterfield England
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 22 Nov to 23 Nov
AU$149
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (1,001 reviews)
"We had a fantastic experience at Ringwood Hall Hotel & Spa! The spa was absolutely wonderful and made for a really relaxing and enjoyable visit. The grounds are stunning. A special mention has to go to all the staff, who were brilliant throughout. Even when things were busy, everyone remained friendly, ..."

Reviewed on 13 Nov 2026

Ringwood Hall Hotel & Spa, BW Signature Collection
Garner Hotel Chesterfield North by IHG

Garner Hotel Chesterfield North by IHG

3 out of 5
3 Tallys End Chesterfield England
Fully refundable
The price is AU$84 per night from 22 Nov to 23 Nov
AU$84
22 Nov - 23 Nov
includes taxes & fees
Garner Hotel Chesterfield North by IHG
See all 5,871 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
All Inclusive Holidays
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beach holidays
Beach Holidays
Beach Holidays

Stay near popular Chesterfield attractions

A historic castle with stone walls, multiple towers, and a set of stone steps leading up to the entrance.
Photo by Barbara Croft
Open Photo by Barbara Croft

Bolsover Castle

9.6/10 (22 reviews)
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.
See properties

What to do in Chesterfield

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

Idyllic England: Derbyshire & the Peak District from Manchester

AU$106
per adult
90% of travellers recommend
Idyllic England: Derbyshire & the Peak District from Manchester
A fun and different way to see Sheffield

Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems

AU$29
per adult
Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems
Peak District

Peak District Road Trip Guidebook: White Peak & Hope Valley

AU$21
per traveller
Peak District Road Trip Guidebook: White Peak & Hope Valley
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.

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