Chesterfield Holidays

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Top hotels in Chesterfield

WILDES INNS

WILDES INNS

4 out of 5
Worksop Road Chesterfield England
Fully refundableReserve now, pay when you stay
The price is S$183 per night from 29 Nov to 30 Nov
S$183
29 Nov - 30 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 S$131 per night from 1 Nov to 2 Nov
S$131
1 Nov - 2 Nov
includes taxes & fees
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 S$74 per night from 8 Nov to 9 Nov
S$74
8 Nov - 9 Nov
includes taxes & fees
8.4/10 Very good! (1,004 reviews)
"Perfect overnight stop over to break up a long journey. Fabulous reception - really helpful and welcoming. Room - everything I needed. Amazing bed and super hot and powerful shower! Faultless stay. Will definitely stay again in the future. Really good internet also."

Reviewed on 27 Oct, 2026

Garner Hotel Chesterfield North by IHG
See all 5,876 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.

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

Peak District

Peak District Road Trip Guidebook: White Peak & Hope Valley

S$19
per traveller
Peak District Road Trip Guidebook: White Peak & Hope Valley
A fun and different way to see Sheffield

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

S$26
per adult
Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems
Bar and Club entry Night Pass to multiple venues in Sheffield

Bar and Club entry Night Pass to multiple venues in Sheffield

S$17
per adult
Bar and Club entry Night Pass to multiple venues in Sheffield
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. 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.