Chesterfield Vacations from $745

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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.
Ville Hotel

Ville Hotel

3 out of 5
Manchester City Centre
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Manchester (MAN)
7.2/10 Good! (53 reviews)
Great value for money with all you need for a couple of nights stay in a really convenient location. Absolutely loved staying on Canal street- a busy and vibrant street in the evening. Deluxe double room at the front was basic but comfortable. If you are wanting luxury though go stay at at the Hilton! Only negatives were shower was so claustrophobic and door was broken and pillows were flat as pancakes. A fan was provided in the room which was great on the really days we stayed but omg- it needed defluffing!

Reviewed on Aug 14, 2025

Treehouse Hotel Manchester

Treehouse Hotel Manchester

4 out of 5
Manchester City Centre
per person
Sep 19 - Sep 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Manchester (MAN)
9.6/10 Exceptional! (231 reviews)
Gorgeous interior design!! We had a family room and it was a great spot and so clean everywhere! Service was a bit hit and miss. Room wasn’t ready on time, she didn’t really tell me anything about services offered until i asked. Breakfast service was not great either! had to ask for everything without being offered. Would come again, but need to think about the customer experience…

Reviewed on Aug 17, 2025

Mitre Hotel Manchester City Centre

Mitre Hotel Manchester City Centre

3 out of 5
Manchester City Centre
per person
Oct 18 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Manchester (MAN)
7/10 Good! (1,000 reviews)
Overall the building was smelly and they have room frangance everywhere to try kill the smell of the old, beauty carpet. It’s a beautiful old building that needs to keep clean with dignity and pride.

Reviewed on Jun 22, 2025

Quay Apartments Manchester

Quay Apartments Manchester

3.5 out of 5
Manchester City Centre
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Manchester (MAN)
9/10 Wonderful! (153 reviews)
Met expectations for inner city apartment and location had a good vibe with bars etc... kitchen was clean with all appliances expected. rooms were smallish so for 4 people kept luggage in lounge area...

Reviewed on Jun 8, 2025

King Street Collection

King Street Collection

4 out of 5
Manchester City Centre
per person
Oct 18 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Manchester (MAN)
No reviews
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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 lively bars 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 top-notch restaurants in this family-friendly area.

Bolsover Castle

What to do in Chesterfield

Bar and Club entry Night Pass to multiple venues in Sheffield

Bar and Club entry Night Pass to multiple venues in Sheffield

$13
per adult
Bar and Club entry Night Pass to multiple venues in Sheffield
Sheffield: Gin Experience - Make Your Own Gin

Sheffield: Gin Experience - Make Your Own Gin

$128
per adult
Sheffield: Gin Experience - Make Your Own Gin
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
See all activities 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
8.6/10 Excellent! (1,001 reviews)
"Only stayed one night for a wedding but thoroughly enjoyed it."

Reviewed on Aug 12, 2025

Get rates
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
$85 nightly
The price is $102 total per night from Aug 25 to Aug 26
$102 total
Aug 25 - Aug 26
Total includes taxes and fees
8/10 Very Good! (924 reviews)
"Lovely hotel in Chesterfield. Very comfortable room, even though furnishings etc were quite dated. Hotel itself full of character and staff very friendly and efficient. Lovely to have breakfast included! Would love to stay again and next time try the spa!"

Reviewed on Jul 29, 2025

Ringwood Hall Hotel & Spa
Radisson Blu Hotel, Sheffield

Radisson Blu Hotel, Sheffield

4 out of 5
Pinstone Street, 30, Sheffield, England
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $114 total per night from Aug 24 to Aug 25
$114 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (411 reviews)
"Great customer service. Lovely breakfast selections."

Reviewed on Aug 13, 2025

Radisson Blu Hotel, Sheffield
See all 5,177 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.

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Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from $745 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.