Chesterfield Holidays
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Top hotels in Chesterfield
WILDES INNS
Worksop Road Chesterfield England
Fully refundableReserve now, pay when you stay
S$167
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very good! (1,010 reviews)
"Breakfast"
Reviewed on 6 Aug, 2026
Ringwood Hall Hotel & Spa, BW Signature Collection
Chesterfield Road Chesterfield England
Fully refundableReserve now, pay when you stay
S$132
9 Aug - 10 Aug
includes taxes & fees
8/10 Very good! (1,002 reviews)
"Booked a suite and never received a dirty, smelly room in my life. A suite is supposed to be a premium room & experience….i wouldn’t let my dog board in it. Mind you, with the smell coming from it there clearly had been dogs staying in it. Window blinds, surface tops and linen all filthy. It should ..."
Reviewed on 6 Aug, 2026
Garner Hotel Chesterfield North by IHG
3 Tallys End Chesterfield England
Fully refundable
S$73
6 Sept - 7 Sept
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"when we arrived and got are room in the bathroom there was a towel with human faeces all over it and we also got kicked out of are room an hour early to someone welcoming themselves in"
Reviewed on 28 Jul, 2026
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.
Stay near popular Chesterfield attractions
Photo by Martin Gerrish
Hardwick Hall
9.6/10 (45 reviews)
You can find out about the history of Ault Hucknall when you stop by Hardwick Hall. Visit the lively bars or top-notch restaurants in this relaxing area.
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 top-notch restaurants in this family-friendly area.
Poolsbrook Country Park
10.0/10 (1 review)
Explore the great outdoors at Poolsbrook Country Park, a lovely green space in Staveley. Visit the spas and lively bars in this relaxing area.
Chesterfield Market
8.4/10 (29 reviews)
You can do some window-shopping at Chesterfield Market during your visit to Chesterfield. Visit the spas and lively bars in this culturally rich area.
Barrow Hill Roundhouse Railway Centre
9.0/10 (4 reviews)
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.
Hardwick Hall-Derbyshire Country Park
10.0/10 (2 reviews)
Explore the great outdoors at Hardwick Hall-Derbyshire Country Park, a lovely green space in Ault Hucknall.
Hotel Van Dyk Theater
8.8/10 (3 reviews)
You can get tickets for a performance at Hotel Van Dyk Theater during your stay in Clowne. Visit the spas and cosy cafes in this relaxing area.
Queen's Park
9.0/10 (10 reviews)
Explore the great outdoors at Queen's Park, a lovely green space in Chesterfield. Visit the spas and cosy cafes in this family-friendly area.
What to do in Chesterfield
Lost in Beauty: Chatsworth & Peak District from Manchester
S$206
per adult
Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems
S$26
per adult
Bar and Club entry Night Pass to multiple venues in Sheffield
S$17
per adult
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?
- Pick your dates: The things you plan to do in Chesterfield and your favourite season can help you decide when to travel.
- 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.
- 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.
- 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
