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.
Crowne Plaza Hotel Manchester City Centre by IHG
Manchester City Centre
CA $1,536
per person
Dec 5 - Dec 9
just found
Roundtrip flight included
Toronto (YYZ) to Manchester (MAN)
9/10 Wonderful! (1,007 reviews)
The front of house lady on reception was brilliant! Nothing was too much trouble! Breakfast was also lovely, staff were really friendly and went out of their way to accommodate all requests.
Reviewed on Sep 27, 2026
voco Manchester City Centre by IHG
Manchester City Centre
CA $1,560
per person
Dec 5 - Dec 9
just found
Roundtrip flight included
Toronto (YYZ) to Manchester (MAN)
9.2/10 Wonderful! (1,378 reviews)
The room was beautiful, decorated lovely clean & very spacious.
Omg that bath, I could of just spent my whole trip chilling in there. Amazing!
The breakfast was lovely, well cooked amazing variety.
Will 100 % stay again.
Reviewed on Sep 26, 2026
Ready to book your vacation to Chesterfield?
Chesterfield Hotel Deals
WILDES INNS
Worksop Road Chesterfield England
Fully refundableReserve now, pay when you stay
CA $139
CA $167 total
Oct 1 - Oct 2
includes taxes & fees
8.4/10 Very good! (1,005 reviews)
"The new part of the hotel is excellent but if you get a room in the older part of the hotel the maitinance needs improving. Bar and wedding facilities excellent. Overall the stay for 2 nights was good."
Reviewed on Sep 27, 2026
Ringwood Hall Hotel & Spa, BW Signature Collection
Chesterfield Road Chesterfield England
Fully refundableReserve now, pay when you stay
CA $119
CA $143 total
Oct 4 - Oct 5
includes taxes & fees
8/10 Very good! (1,002 reviews)
"The room was clean and bed comfy. BBC tv coverage bad. Bathroom needs upgrading. Room 115. Breakfast good but chaotic - there was not enough info on ordering various items and what order to move around the various item tables. Finding staff to take order not easy. Staff were v pleasant. Reception ..."
Reviewed on Sep 26, 2026
Garner Hotel Chesterfield North by IHG
3 Tallys End Chesterfield England
Fully refundable
CA $66
CA $79 total
Oct 18 - Oct 19
includes taxes & fees
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.
Stay near popular Chesterfield attractions
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 lively bars in this relaxing area.
Photo by Phil Betesta
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.
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 lively bars in this culturally rich 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.
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 lively bars in this family-friendly area.
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 top-notch restaurants in this relaxing area.
SMH Group Stadium
Catch an event at SMH Group Stadium during your trip to Chesterfield. Savor the top-notch restaurants and lively bars while in town.
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.
What to do in Chesterfield
Idyllic England: Derbyshire & the Peak District from Manchester
CA $116
per adult
90% of travellers recommend
Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems
CA $28
per adult
Bar and Club entry Night Pass to multiple venues in Sheffield
CA $19
per adult
Frequently asked questions
How much does a Chesterfield vacation package cost?
Offering excellent value package deals from CA $1,436 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?
- 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.
- 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.
- 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.
- 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.
