Chesterfield Vacation Packages

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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!

Top Chesterfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Aston Court Derby City Centre by Belvilla

Aston Court Derby City Centre by Belvilla

3 out of 5
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MAN)
8/10 Very Good! (606 reviews)
Friendly staff - easy check in

Reviewed on Jul. 5, 2025

Treehouse Hotel Manchester

Treehouse Hotel Manchester

4 out of 5
Manchester City Centre
per person
Sep 9 - Sep 13
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MAN)
9.6/10 Exceptional! (110 reviews)
Unique decor, lovely aroma from the moment you walk in. Staff very friendly.

Reviewed on Jul. 6, 2025

The Alan

The Alan

4 out of 5
Manchester City Centre
per person
Sep 9 - Sep 13
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MAN)
8.6/10 Excellent! (1,003 reviews)
I had a great stay and would stay again and also recommend to others. Easy to get around, my stay was based on attending the Albert Hall which was literally less than a 10min walk.

Reviewed on Jun. 29, 2025

Ecclesall Road Apartment

Ecclesall Road Apartment

2 out of 5
per person
Aug 22 - Aug 28
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MAN)
No reviews
BrewDog DogHouse Manchester

BrewDog DogHouse Manchester

4 out of 5
Manchester City Centre
per person
Sep 9 - Sep 13
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MAN)
9.8/10 Exceptional! (342 reviews)
Our first time at one of the Brewdog hotels, and we loved it. Exactly the vibe we expected, and wanted: casual, cool, fun, not stuffy at all. Excellent amenities too. The only thing you need to be aware of is that the bathrooms do not afford a lot of privacy, so if you're shy about such things you might end up using the loos in the bar downstairs.

Reviewed on Jun. 18, 2025

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Chesterfield Hotel Deals

Casa Hotel
Casa Hotel
4 out of 5
Lockoford Lane, Chesterfield, England
9.4/10 Exceptional! (1,000 reviews)
"Great hotel with easy access to Peak District. Free parking available."

Reviewed on Jun. 27, 2025

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Casa Hotel
Ringwood Hall Hotel & Spa
Ringwood Hall Hotel & Spa
4 out of 5
Chesterfield Road, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jul 9 to Jul 10
CA $150
CA $180 total
Jul 9 - Jul 10
includes taxes & fees
8/10 Very Good! (902 reviews)
"Great property, clean and comfy"

Reviewed on Jun. 30, 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
The price is CA $136 per night from Aug 6 to Aug 7
CA $136
CA $164 total
Aug 6 - Aug 7
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Really nice hotel, very clean and new, however it was bit pricey in the bar and restaurant, although had a nice meal. All good.."

Reviewed on Jun. 30, 2025

WILDES INNS
See all 5,337 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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What to do in Chesterfield

eSIM: Airalo Europe Package - United Kingdom

eSIM: Airalo Europe Package - United Kingdom

CA $4
per traveller
eSIM: Airalo Europe Package - United Kingdom
Small-Group Derbyshire, the Peak District & Poole's Cavern

Idyllic England: Derbyshire & the Peak District from Manchester

CA $133
per adult
84% of travellers recommend
Idyllic England: Derbyshire & the Peak District from Manchester
7 Hours Pub Tours in Peak District

7 Hours Pub Tours in Peak District

CA $232
per adult
7 Hours Pub Tours in Peak District
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering excellent value package deals from CA $853 on Expedia, you'll be pleasantly surprised at how much a vacation to Chesterfield costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Chesterfield?
January, April and September are great times to look for cheap Chesterfield vacation packages. Travelling in less busy periods means you can generally find lower prices on hotels and flights.
How many days is enough for Chesterfield?
Dedicate around 2 days for your Chesterfield vacation to enjoy all that makes this destination unique. Stroll around popular neighbourhoods, including Spital and Hasland. Then make a beeline for top attractions such as Barrow Hill Roundhouse Railway Centre and Queen's Park. With a well-planned itinerary, you can keep busy with room for some relaxation too. Want to venture beyond Chesterfield? Consider a day trip or two.
Is it worth booking a vacation package to Chesterfield?
Chesterfield has everything you need for an amazing break --- cycling, views and walking trails are just the start. Whether you want to visit attractions such as Barrow Hill Roundhouse Railway Centre and Queen's Park, or take the road less travelled, you'll have plenty to see and do on your Chesterfield vacation.
How to find the best Chesterfield package deals?
Use Expedia's filters to find some tempting Chesterfield package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Chesterfield package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the freedom to create a customized Chesterfield vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Chesterfield?
If you're considering a spur-of-the-moment Chesterfield trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterfield?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred season and the available activities will also help you decide when to escape to Chesterfield.
  2. Set a budget: Consider costs like flights, transportation and food when calculating how much to put aside for your trip to Chesterfield. Then, pick a property that fits your budget, whether that's an affordable stay or a deluxe retreat.
  3. Decide your trip length: Think about how long you'd like to spend discovering Chesterfield. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Chesterfield vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.