Chesterfield Vacations from $1,116

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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.
Pymgate Lodge Hotel

Pymgate Lodge Hotel

3 out of 5
Price was $1,280, price is now $1,116 per person
$1,116
per person
Aug 11 - Aug 17
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Manchester (MAN)
8.6/10 Excellent! (409 reviews)
Warm welcome, lovely hotel. Clean room with everything you need. Tea and coffee. Comfy bed. Would stay again.

Reviewed on Apr 26, 2026

Cottage in Bowland Near Clitheroe Castle

Cottage in Bowland Near Clitheroe Castle

2 out of 5
Price was $2,327, price is now $1,701 per person
$1,701
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Manchester (MAN)
No reviews

Trafford Hall Hotel Manchester, A Brilliant Hotels Collection

Trafford Hall Hotel Manchester, A Brilliant Hotels Collection

4 out of 5
Old Trafford
Price was $1,526, price is now $1,255 per person
$1,255
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Manchester (MAN)
7.6/10 Good! (454 reviews)
Very nice hotel. Great location and easy to find.

Reviewed on Jun 28, 2026

Treehouse Hotel Manchester

Treehouse Hotel Manchester

4 out of 5
Manchester City Centre
Price was $1,656, price is now $1,381 per person
$1,381
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Manchester (MAN)
9.4/10 Exceptional! (801 reviews)
Amazing staff, beautiful room, every little detail of the hotel was perfect. Thank you so much for a brilliant stay, this is my hotel whenever i come back to Manchester

Reviewed on Jun 28, 2026

Quay Apartments Exchange Quay

Quay Apartments Exchange Quay

4 out of 5
Price was $1,514, price is now $1,266 per person
$1,266
per person
Aug 11 - Aug 17
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Manchester (MAN)
9.4/10 Exceptional! (99 reviews)
Great property and location

Reviewed on Jun 21, 2026

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Stay near popular Chesterfield attractions

A historic building with a prominent tower and a large magnolia tree in the foreground.
Photo by Martin Gerrish
Open 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 lively bars or top-notch restaurants in this relaxing area.
See properties

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

$126
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

$20
per adult
Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems
See all activities in Chesterfield

Chesterfield Hotel Deals

WILDES INNS

WILDES INNS

4 out of 5
Worksop Road Chesterfield England
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $101 total per night from Jul 12 to Jul 13
$101 total
Jul 12 - Jul 13
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
"Good air con. Plenty of parking extra at rear. Clean room. Lots of light switches but only 1 worked. No shelf in shower to stand anything on. Taps in sink not enough height to get kettle access. Corridor lit very dim a bit creepy for ladies on their own. Price of drinks in bar were extortionate. ..."

Reviewed on Jun 27, 2026

WILDES INNS
Garner Hotel Chesterfield North by IHG

Garner Hotel Chesterfield North by IHG

3 out of 5
3 Tallys End Chesterfield England
Fully refundable
$53 nightly
The price is $64 total per night from Jul 19 to Jul 20
$64 total
Jul 19 - Jul 20
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
"Can't fault it. Room was great. Good value for money."

Reviewed on Jul 2, 2026

Garner Hotel Chesterfield North by IHG
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
$79 nightly
The price is $95 total per night from Jul 19 to Jul 20
$95 total
Jul 19 - Jul 20
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"Great property, some TLC needed to the rooms and decor, but the friendly staff made up for it"

Reviewed on Jun 5, 2026

Ringwood Hall Hotel & Spa, BW Signature Collection
See all 5,448 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.

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 $1,116 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.