Chesterfield Vacations from $1,588
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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.
Berkeley Square Apartments
$1,588
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MAN)
8.4/10 Very Good! (5 reviews)
The apartment was absolutely immaculate. Easy check in and all amenities were clean and modern. Looking to come back again really soon. Great service from the host Sean and security at the front door were all very helpful and kind. Thank you
Reviewed on Jul 22, 2026
Treehouse Hotel Manchester
Manchester City Centre
$1,589
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MAN)
9.4/10 Exceptional! (848 reviews)
Very helpful staff, early checkin was possible and the room was amazing in that it was quirky and different but also a high standard, comfortable and clean.
Filtered water was on every floor, well kitted out gym although we didn't get chance to use it.
Breakfast was fantastic, quick service and the bar staff where very helpful
The hotel is located very central in Manchester so super convenient for anything, there was a little noise from ironically the hotel outside bar in the afternoon but that was turned off around 10 and then it was very peaceful.
Reviewed on Aug 8, 2026
The Lowry Hotel Manchester
Manchester City Centre
$1,588
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MAN)
9.2/10 Wonderful! (1,008 reviews)
Great place! Wonderful decor and service. I love the different quotes about the city on each floor.
Reviewed on Aug 9, 2026
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Photo by Martin Gerrish
Hardwick Hall
9.6/10 (45 reviews)
You can find out about the history of Ault Hucknall with a visit to Hardwick Hall. Check out the top-notch restaurants or lively bars 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 visit to Bolsover Castle. Check out 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. Check out the spas and top-notch restaurants in this relaxing area.
Chesterfield Market
8.4/10 (29 reviews)
You can do some window-shopping at Chesterfield Market during your trip to Chesterfield. Check out the spas and top-notch restaurants in this family-friendly area.
Barrow Hill Roundhouse Railway Centre
9.0/10 (4 reviews)
You can spend an afternoon studying the exhibits at Barrow Hill Roundhouse Railway Centre during your travels 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 make plans for a show at Hotel Van Dyk Theater on your trip to Clowne. Check out the spas and charming coffeehouses 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. Check out the spas and charming coffeehouses in this family-friendly area.
What to do in Chesterfield
Sheffield: Gin Distillery Tasting Visit with Guided Tour
$24
per adult
Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems
$20
per adult
Sheffield: Gin Experience - Make Your Own Gin
$126
per adult
Chesterfield Hotel Deals
WILDES INNS
Worksop Road Chesterfield England
Fully refundableReserve now, pay when you stay
$101 nightly
$121 total
Aug 18 - Aug 19
Total with taxes and fees
Ringwood Hall Hotel & Spa, BW Signature Collection
Chesterfield Road Chesterfield England
Fully refundableReserve now, pay when you stay
$86 nightly
$103 total
Aug 24 - Aug 25
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
"Obviously seen better days, the gardens are lovely. The food at dinner and breakfast was average. Lots of young staff who did their best. The bed was comfortable but no shower just a bath in my room."
Reviewed on Aug 8, 2026
Garner Hotel Chesterfield North by IHG
3 Tallys End Chesterfield England
Fully refundable
$47 nightly
$57 total
Sep 6 - Sep 7
Total with taxes and 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 Jul 28, 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.
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 $1,588 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?
- Choose your dates: What you plan to do in Chesterfield and your preferred season will help you decide when to go.
- 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.
- 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.
- 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.
- Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the perfect Chesterfield vacation package for you.
- 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.
Explore a world of travel with Expedia
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- Visit Brimington
- Visit Pilsley
- Barlow Vacations
- Brimington Vacations
- Bramall Lane
- Visit Tibshelf
- Sheffield Jewish Synagogue
- Sheffield Winter Garden
- Peace Gardens
- Sheffield Botanical Gardens
- Visit Barlborough
- Mecca Bingo
- Visit Old Brampton
- Visit Hardstoft
- Crucible Theatre
- Sheffield City Hall
- Sheffield Manor Lodge
- Visit Derbyshire
- Sheffield Town Hall
- Visit Clay Cross
- Ponds Forge International Sports Centre
- Graves Art Gallery
- Visit Sheffield
- Crich Tramway Village
- Visit Marsh Lane
- Visit Clowne
- Visit Unstone
- Visit Stonedge
- Rother Valley Country Park
- Visit Chesterfield
- Endcliffe Park
- Visit Kelstedge
- Visit Dronfield
- Visit Shirebrook
- Chatsworth House Labyrinth
- Visit Mosborough
- Visit Millthorpe
- Sheffield Hallam University
- Heights of Abraham Cable Car Station
- Sheffield Vacations
- Visit Totley
- Visit Tupton
- Mecca Bingo
- Forge Dam
- Visit Duckmanton
- Visit Cutthorpe
- Haddon Hall Manor
- Renishaw Hall
- Visit Eckington
- Lumsdale Valley
- Chatsworth House
- Poolsbrook Country Park
- Beauchief Abbey
- Visit Holymoorside
- Visit Ashover
- Hardwick Hall
- Visit Woolley Moor
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
