Chesterfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chesterfield

Casa Hotel
Casa Hotel
4 out of 5
Lockoford Lane, Chesterfield, England
9.4/10 Exceptional! (1,001 reviews)
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Reviewed on 20 Jun 2025

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Casa Hotel
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 2.064.223 ₫ per night from 29 Jun to 30 Jun
2.064.223 ₫
2.477.067 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (895 reviews)
"Plenty of parking available, reception very welcoming. Quite a trip to the room, up and down stairs so if you struggle with that, maybe ask for an easier room. Food was very good but the restaurant staff very forgetful."

Reviewed on 19 Jun 2025

Ringwood Hall Hotel & Spa
WILDES INNS
WILDES INNS
4 out of 5
Worksop Road, Clowne, Chesterfield, England
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,000 reviews)
"Amazing hotel"

Reviewed on 13 Jun 2025

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WILDES INNS
See all 5,246 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.

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.

Popular places to visit

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

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

Hotel Van Dyk Theater

You can get tickets for a performance at Hotel Van Dyk Theater during your stay in Chesterfield. Visit the spas and lively bars in this relaxing area.

Hotel Van Dyk Theater