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

Macdonald Old England Hotel & Spa

Macdonald Old England Hotel & Spa

4 out of 5
per person
Jun. 4 - Jun. 11
Roundtrip flight included
Calgary (YYC) to Manchester (MAN)
8.2/10 Very Good! (1,000 reviews)
Really good, clean rooms, friendly staff, a view to die for, also really comfortable, it strikes the correct balance between being really homely and having everything you would need in a hotel room in this day and age without feeling outdated or tacky.

Reviewed on Apr. 6, 2024

The Belsfield Hotel

The Belsfield Hotel

4 out of 5
per person
Jun. 4 - Jun. 11
Roundtrip flight included
Calgary (YYC) to Manchester (MAN)
8.6/10 Excellent! (1,000 reviews)
Very good place to stay

Reviewed on Apr. 14, 2024

Town House

Town House

3 out of 5
per person
Jun. 4 - Jun. 11
Roundtrip flight included
Calgary (YYC) to Manchester (MAN)
No reviews
Pine Lake Resort

Pine Lake Resort

4 out of 5
per person
Jun. 4 - Jun. 11
Roundtrip flight included
Calgary (YYC) to Manchester (MAN)
9.2/10 Wonderful! (1,050 reviews)
A fantastic stay for my small family. Lodge was lovely, nice and spacious. Activities on site were great.

Reviewed on Apr. 15, 2024

Staycity Aparthotels, Manchester, Piccadilly

Staycity Aparthotels, Manchester, Piccadilly

4 out of 5
Manchester City Centre
per person
Jun. 23 - Jun. 30
Roundtrip flight included
Toronto (YYZ) to Manchester (MAN)
9.2/10 Wonderful! (1,739 reviews)
Brilliant stay at StayCity-staff were so friendly and the apartment was very clean and had everything we needed. An excellent location right beside the train station and the free bus was right outside. Would definitely staff here again

Reviewed on Apr. 11, 2024

Prices and availability subject to change. Additional terms may apply.

Chesterfield Hotel Deals

WILDES Derbyshire
WILDES Derbyshire
4 out of 5
Worksop Road, Clowne, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Apr. 22 to Apr. 23
CA $127
CA $153 total
includes taxes & fees
Apr 22 - Apr 23
8.6/10 Excellent! (840 reviews)
Fantastic room and facilities
"Beautiful Wedding for Friends, The room was lovely, the bed very comfortable, large walk in shower, overall a very beautifully decorated room"

Reviewed on Apr. 12, 2024

WILDES Derbyshire
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 $112 per night from May 6 to May 7
CA $112
CA $134 total
includes taxes & fees
May 6 - May 7
8.2/10 Very Good! (762 reviews)
"The room was a little dated, lovely corner bath but the jets weren’t working on it, no shower in the room which would have been handy. Lovely 4 poster bed, but the mattress was way too soft. Restaurant was lovely and the quality of the food was great. We used the spa and the gym the following day, ..."

Reviewed on Apr. 14, 2024

Ringwood Hall Hotel & Spa
Casa Hotel
Casa Hotel
4 out of 5
Lockoford Lane, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Apr. 21 to Apr. 22
CA $172
CA $206 total
includes taxes & fees
Apr 21 - Apr 22
9.4/10 Exceptional! (923 reviews)
"Really nice hotel"

Reviewed on Apr. 14, 2024

Casa Hotel
See all 4,661 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?
Maybe less than you might think — from as low as CA $1,534, in fact! By bundling hotels, flights and car rentals into a customized travel package, your trip to Chesterfield is just a few clicks away.
How do I get a cheap travel package to Chesterfield?
Booking a Chesterfield vacation package with Expedia is a smart way to save. We offer access to over 550 partner airlines and 1,000,000 hotel options all over the world. With such a broad range to pick from, you’ll have no worries pulling together your perfect escape.
Where should I stay in Chesterfield?
It makes sense to stay near the action. Many people book hotels in the vicinity of popular sights, such as Bolsover Castle, Hardwick Hall and Chesterfield Market.
What are the top hotels in Chesterfield?
Casa Hotel and Van Dyk by Wildes are among the best options in the Tupton neighborhood. If you’d like to stay in the Wingerworth area, consider getting a room at ibis Chesterfield Centre – Market Town or ibis Chesterfield North - Barlborough.
How far in advance should I book my Chesterfield vacation?
Reserving your tickets early with Expedia means one less thing to have to worry about. Many air carriers advertise prices up to 12 months prior to take off. This is often the cheapest time to book. If circumstances have left you booking late, great deals to Chesterfield sometimes become available a few weeks before departure.
What does an Expedia Chesterfield travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply choose your favorite bundle and get access to incredible deals. Once you’ve made your booking, add on some sightseeing tours and watch your savings grow. When it comes to organizing your Chesterfield trip, you’re in charge!
What should I know before booking a Chesterfield travel package?
Whether it’s adventure or relaxation you’re chasing, a Chesterfield vacation package lets you plan your escape your way. Plus, you’ll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the more you’ll save!
Can I choose my airline with a Chesterfield Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you’d prefer to fly to Chesterfield in economy or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Chesterfield vacation package?
You sure can, and we’re here to help. You may be able to cancel or amend your Chesterfield vacation package for free within 24 hours of booking. However, you may be charged a fee by your hotel, airline or car rental company for older bookings. If life throws you a curveball, take a look at our Customer Service Portal for further information.

Discover the most popular places to visit in Chesterfield

Image for 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
Image for 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 charming coffeehouses in this family-friendly area.

Mecca Bingo
Image for Bolsover Castle

Bolsover Castle

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.

Bolsover Castle

What to do in Chesterfield

Image for eSIM: Airalo Europe Package - United Kingdom

eSIM: Airalo Europe Package - United Kingdom

CA $8
Per adult
eSIM: Airalo Europe Package - United Kingdom
See all activities in Chesterfield

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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.