Chesterfield Vacations from $805

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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.
The Alan

The Alan

4 out of 5
Manchester City Centre
Price was $987, price is now $805 per person
$805
per person
Dec 8 - Dec 12
found 11 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MAN)
8.6/10 Excellent! (1,088 reviews)
Great accomodation close to CBD and historic sites, old buildings we wanted to see. Room was beautifully made up

Reviewed on Oct 10, 2025

INNSiDE by Meliá Manchester

INNSiDE by Meliá Manchester

4 out of 5
Manchester City Centre
Price was $1,749, price is now $1,169 per person
$1,169
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MAN)
9.2/10 Wonderful! (1,007 reviews)
Would prefer a bathroom with a door! Very modern, not very modest.

Reviewed on Oct 12, 2025

Treehouse Hotel Manchester

Treehouse Hotel Manchester

4 out of 5
Manchester City Centre
Price was $1,366, price is now $946 per person
$946
per person
Dec 8 - Dec 12
found 11 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MAN)
9.4/10 Exceptional! (320 reviews)
Lovely room, staff and restaurant. Decent location. Highly recommended.

Reviewed on Oct 12, 2025

Manchester Portland By Sunday

Manchester Portland By Sunday

3.5 out of 5
Manchester City Centre
Price was $1,029, price is now $847 per person
$847
per person
Dec 8 - Dec 12
found 11 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MAN)
8.4/10 Very Good! (1,358 reviews)
5 minute walk from Picadilly station, upon arrival staff nice and friendly, room was clean and beds were comfy, convenient to places we needed ie ao arena, breakfast next morning was enough and mixture of cooked and cold foods (if i had one complaint they stopped the buffet style and said order from kitchen but we had alread had enough), check was easy.

Reviewed on Oct 12, 2025

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Discover the most popular places to visit in Chesterfield

Hardwick Hall

Hardwick Hall

You can find out about the history of Chesterfield with a visit to Hardwick Hall. Check out the lively bars or top-notch restaurants in this relaxing area.

Hardwick Hall
Mecca Bingo

Mecca Bingo

Why not try your luck with a visit to Mecca Bingo during your travels in Chesterfield? Check out the spas and top-notch restaurants in this family-friendly area.

Mecca Bingo

Bolsover Castle

You can find out about the history of Bolsover with a visit to Bolsover Castle. Check out the spas and lively bars in this relaxing area.

Bolsover Castle

What to do in Chesterfield

Sheffield: Gin Distillery Tasting Visit with Guided Tour

Sheffield: Gin Distillery Tasting Visit with Guided Tour

$24
per adult
Sheffield: Gin Distillery Tasting Visit with Guided Tour
Sheffield: Gin Experience - Make Your Own Gin

Sheffield: Gin Experience - Make Your Own Gin

$127
per adult
Sheffield: Gin Experience - Make Your Own Gin
A fun and different way to see Sheffield

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

$33
per traveler
Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems
See all activities in Chesterfield

Chesterfield Hotel Deals

Ringwood Hall Hotel & Spa

Ringwood Hall Hotel & Spa

4 out of 5
Chesterfield Road, Chesterfield, England
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $100 total per night from Oct 20 to Oct 21
$100 total
Oct 20 - Oct 21
Total with taxes and fees
8/10 Very Good! (945 reviews)
"We stayed for a last minute break with our dog. The room was spacious and clean. A lovely big bathroom. We had drinks in the bar at night and a nice breakfast the next morning. We really enjoyed it. The staff were lovely, made a fuss of our dog and made us feel more than welcome."

Reviewed on Oct 11, 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! (1,013 reviews)
"Overall the stay was good but did find for a two night stay there was insufficient supplies of milk and coffee in the room and breakfast was a little haphazard with toaster taking ages and having to wait for items of breakfast to be replenished."

Reviewed on Oct 11, 2025

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WILDES INNS
Olde House, Chesterfield by Marston's Inns

Olde House, Chesterfield by Marston's Inns

4 out of 5
Loundsley Green Rd, Chesterfield, England
Fully refundableReserve now, pay when you stay
$56 nightly
The price is $68 total per night from Nov 2 to Nov 3
$68 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (301 reviews)
"Hotel was clean and very near to Chesterfield for us to go to an appointment"

Reviewed on Oct 10, 2025

Olde House, Chesterfield by Marston's Inns
See all 5,145 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.

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 $805 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.