Chesterfield Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Chesterfield Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Cove Minshull Street

Cove Minshull Street

4 out of 5
Manchester City Centre
per person
14 May - 17 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Manchester (MAN)
9.4/10 Exceptional! (543 reviews)
Photos were not like the actual property.

Reviewed on 9 Feb,2025

Native Manchester

Native Manchester

4.5 out of 5
Manchester City Centre
per person
14 May - 17 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Manchester (MAN)
9.2/10 Wonderful! (703 reviews)
Great spot near Piccadilly station to stay. Cool bar and restaurant attached to the hotel. Rooms very big and comfortable. Would stay again.

Reviewed on 11 Feb,2025

Wilde Aparthotels, Manchester, St. Peter’s Square

Wilde Aparthotels, Manchester, St. Peter’s Square

4 out of 5
Manchester City Centre
per person
14 May - 17 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Manchester (MAN)
9.4/10 Exceptional! (1,095 reviews)
Very nice hotel have stayed in the past - would stay again!

Reviewed on 8 Feb,2025

CitySuites 2 Aparthotel

CitySuites 2 Aparthotel

5 out of 5
Greengate
per person
14 May - 17 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Manchester (MAN)
9.4/10 Exceptional! (343 reviews)
My stay at the property was lovely, a great spa pool, it close to lovely shopping centres.

Reviewed on 30 Dec,2024

Whitworth Locke

Whitworth Locke

4 out of 5
Manchester City Centre
per person
14 May - 17 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Manchester (MAN)
9.4/10 Exceptional! (1,039 reviews)
Brilliant staff and a great space

Reviewed on 15 Feb,2025

Top hotels in Chesterfield

Casa Hotel
Casa Hotel
4 out of 5
Lockoford Lane, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is S$199 per night from 23 Feb to 24 Feb
S$199
includes taxes & fees
23 Feb - 24 Feb
9.4/10 Exceptional! (1,000 reviews)
Welcoming Hotel
"Comfortable rooms with everything you need for work and play, restaurant and bar service with a smile"

Reviewed on 6 Feb,2025

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 S$119 per night from 3 Mar to 4 Mar
S$119
includes taxes & fees
3 Mar - 4 Mar
8/10 Very Good! (855 reviews)
"Lovely relaxing break, lovely staff"

Reviewed on 10 Feb,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 S$151 per night from 2 Mar to 3 Mar
S$151
includes taxes & fees
2 Mar - 3 Mar
8.6/10 Excellent! (1,002 reviews)
"The staff were very helpful, respectful but friendly. I was at a course near the hotel on Sunday so was slightly disappointed the restaurant was late opening on Sunday morning. I did however get to my work on time! I would definitely stay at Wildes hotel again. Thank you"

Reviewed on 16 Feb,2025

WILDES INNS
See all 5,091 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.

Frequently asked questions

How much does a Chesterfield holiday package cost?
Offering great value package deals from S$1,286 on Expedia, you’ll be surprised at how little a holiday 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 hoping to snag a cheap Chesterfield holiday package, consider travelling in January, April and September. You’ll generally find better prices on flights and accommodation during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Chesterfield?
Dedicate at least 2 days for your Chesterfield holiday in order to enjoy everything that makes this destination special. Stroll around popular areas, including Spital and Hasland. Then check out top sights like Pomegranate Theatre and Chesterfield Museum & Art Gallery. With a well-organised itinerary, you can keep busy with room for some rest time too. Want to travel outside of Chesterfield? Consider an excursion or two.
Is it worth booking a holiday package to Chesterfield?
Chesterfield has all the ingredients you need for an amazing getaway — 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 traveled, there’s plenty to experience on your Chesterfield holiday.
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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can customise 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 holiday 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. Pick your dates: The things you plan to do in Chesterfield and your favourite season can help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and experiences. Your hotel will probably be the biggest expense during your trip to Chesterfield.
  3. Determine how many days away: Start by compiling a list of the attractions you’d like to get to in Chesterfield. Then, estimate how long you’ll need at each, along with any travel time.
  4. Bundle your accommodation and airfare: After you’ve settled on your dates and duration, lock in the ideal Chesterfield holiday package for you.

Popular places to visit

Poolsbrook Country Park

Explore the great outdoors at Poolsbrook Country Park, a lovely green space in Staveley. Visit the spas and cosy cafes in this relaxing area.

Poolsbrook Country Park

What to do in Chesterfield

Small-Group Derbyshire, the Peak District & Poole's Cavern

Idyllic England: Derbyshire & the Peak District from Manchester

S$87
per adult
84% of travellers recommend
Idyllic England: Derbyshire & the Peak District from Manchester
Private Shopping Tour from Sheffield to Outlet East Midlands

Private Shopping Tour from Sheffield to Outlet East Midlands

S$155
per adult
Private Shopping Tour from Sheffield to Outlet East Midlands
Private Shopping Tour from Sheffield to Designer Outlet York

Private Shopping Tour from Sheffield to Designer Outlet York

S$281
per adult
Private Shopping Tour from Sheffield to Designer Outlet York
See all activities in Chesterfield

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.