Chesterfield Vacations from $475

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Your Chesterfield Vacation

A great way to experience this exciting city is with a tailor-made Chesterfield vacation package. Base yourself in the neighborhood of Shirland, which is good for culture, golfing and history or go someplace else — our packages are all about you. Eager to start exploring your surroundings? Bolsover Castle, Chesterfield Market and Barrow Hill Roundhouse Railway Centre are just three of the best places to visit during a trip to Chesterfield. Stop daydreaming and start adventuring. Browse the broad range of options on Expedia today and finally put your Chesterfield vacation plans into motion!

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
OYO Cornerstone Manor Hotel
Manchester Portland By Sunday
Oddfellows on the Park
Manchester University
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Discover the most popular places to visit in Chesterfield

What to do in Chesterfield

Chesterfield Hotel Deals

WILDES INNS

WILDES INNS

4 out of 5
Worksop Road, Clowne, Chesterfield, England
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $124 total per night from Nov 23 to Nov 24
$124 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
All good many thanks !

Reviewed on Nov 2, 2025

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
$73 nightly
The price is $87 total per night from Nov 9 to Nov 10
$87 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (956 reviews)
A great place for an overnight journey break, excellent breakfast and friendly staff. Room was a little dated but clean and in keeping with the style you’d expect of the period. The EV chargers were easy to use and worked without issue. Just wish we could have spent some more time there to ...

Reviewed on Nov 4, 2025

Ringwood Hall Hotel & Spa
Twin Oaks Hotel

Twin Oaks Hotel

3 out of 5
Church Lane, Chesterfield, England
8.6/10 Excellent! (413 reviews)
Room was clean and comfortable. Staff friendly and helpful

Reviewed on Nov 1, 2025

Twin Oaks Hotel
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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
East Midlands Airport (EMA)
Population
113,100
Max Temp Winter
45ºF
Max Temp Summer
65ºF
Top Sights
Bolsover Castle, Hotel Van Dyk Theater and Pomegranate Theatre

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Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from $475 on Expedia, you'll be surprised at how little a vacation 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 looking to score a cheap Chesterfield vacation package, consider traveling in May, July and December. You'll usually find better prices on hotels and airfares during these months — perfect for a budget-friendly break.
How many days is enough for Chesterfield?
Chesterfield vacations can be short or long, but to get a real feel for this destination, we think 2 days is a good ballpark. This will mean you can fit in top sights like Pomegranate Theatre and Chesterfield Museum & Art Gallery as well as lesser-known spots. Don't forget to visit cool areas such as Spital and Hasland either. If you're clever with your time, you may even be able to take a day trip outside of Chesterfield too.
Is it worth booking a vacation package to Chesterfield?
Whether you're looking to visit top attractions such as Chesterfield Market and Barrow Hill Roundhouse Railway Centre on your Chesterfield vacation, or coming for its excellent family-friendly attractions, walking trails and nature, there's something for everyone here. With so much to do, you'll soon learn why so many travelers think Chesterfield is a good vacation destination.
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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can customize 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 vacation 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. Choose your dates: What you plan to do in Chesterfield and your preferred season will help you decide when to go.
  2. Figure out your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Chesterfield.
  3. Organize your Chesterfield escape with Expedia's trip planning tool: Look for and book stays and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Chesterfield together.
  4. Work out your trip length: Consider how much time you want to spend exploring Chesterfield. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  5. Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the perfect Chesterfield vacation package for you.
  6. Add on experiences and excursions: Take a look at our travel guide to find some exciting things to do in Chesterfield. Book tickets or make reservations before you go to save time and skip the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
If you're like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Chesterfield break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.

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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.