Chesterfield Holidays from £157

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Your Chesterfield Holiday

A great way to experience this exciting city is with a tailor-made Chesterfield holiday package. Base yourself in the neighbourhood 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 holiday plans into motion!

Top Chesterfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Broadfield Park Hotel Rochdale

Broadfield Park Hotel Rochdale

Save 100% on your flight
£157
per person
23 Oct - 26 Oct
found 24 hours ago
Return flight included
Belfast (BFS) to Manchester (MAN)
6.8/10 (386 reviews)
Treehouse Hotel Manchester

Treehouse Hotel Manchester

Manchester City Centre
Save 100% on your flight
£342
per person
4 Dec - 6 Dec
found 1 day ago
Return flight included
Belfast (BFS) to Manchester (MAN)
9.4/10 Exceptional! (869 reviews)
Milverton Court by OYO

Milverton Court by OYO

Save 100% on your flight
£222
per person
23 Oct - 26 Oct
found 24 hours ago
Return flight included
Belfast (BFS) to Manchester (MAN)
7/10 Good! (24 reviews)
The Internet was down when I checked. Which was sorted promptly and a member of staff came to let me know. It was remote check in . No staff to see. But the staff was efficient and polite. The room was clean, comfortable and seamed to have been recently refurbished. It was above a restaurant that I never found to be open. There was a bar on site that was quiet and never disturbed me. My only issue with the area was I struggle to get food that I as okay with As I can have a delicate stomach. I'm not sure on afghan food. But a busy food street 15 min walk way.

Reviewed on 11 Sept 2026

Forty Seven Hotel Manchester, WorldHotels Crafted

Forty Seven Hotel Manchester, WorldHotels Crafted

Manchester City Centre
Save 100% on your flight
£255
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Belfast (BFS) to Manchester (MAN)
8.8/10 Excellent! (247 reviews)
Don’t order breakfast it’s a basket. I was charged a commission amount which was incorrect, but was resolved . No milk to make hot drink in your room . Little things matter

Reviewed on 7 Sept 2026

Timann Place

Timann Place

Save 100% on your flight
£176
per person
23 Oct - 26 Oct
found 24 hours ago
Return flight included
Belfast (BFS) to Manchester (MAN)
6/10 (1 review)

Things to do in and around Chesterfield

Chesterfield offers a delightful blend of outdoor activities and scenic beauty, perfect for adventure seekers. Explore picturesque walks and cycling opportunities, while also enjoying fishing spots around the area. The town features a variety of recreational spaces, shopping centres, and malls, ensuring ample options for leisure and exploration. With its charming scenery, Chesterfield is an ideal destination for those who love sightseeing and nature.

Shopping

Chesterfield Market offers a vibrant atmosphere with a variety of local stalls perfect for gifts and souvenirs. If you're up for a drive, visit Meadowhall Shopping Centre, 19.3km away, for a larger selection, or Denby Pottery, 24.1km away, known for its exquisite ceramics.

Recreation

At Ponds Forge International Sports Centre, enjoy a range of wellness activities including swimming and leisure facilities, perfect for unwinding. Experience the vibrant atmosphere of Sheffield City Hall for a lively concert, or immerse yourself in culture and romance at the Hotel Van Dyk Theater, ideal for family outings.

Adventure

Experience the thrill of hot air ballooning with Virgin Balloon Flights, located 16.1km from Chesterfield, offering breathtaking views. For family fun, visit The Play Arena, 14.5km away, filled with arcade excitement. Alternatively, embark on the Sheffield Round Walk, also 16.1km out, for stunning outdoor scenery.

Nightlife

For a lively nightlife experience in Chesterfield, visit Ye Olde Trip to Jerusalem and The Hemlock Stone, both offering romantic vibes and entertainment just a short distance away. Alternatively, Goffs UK provides a vibrant atmosphere for an enjoyable night out, adding to the town's diverse nightlife scene.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Chesterfield

Chesterfield offers a delightful blend of outdoor adventures and rich history, making it an ideal destination for those seeking culture and family experiences. Visitors can explore the scenic Chesterfield Canal, delve into local history at the Chesterfield Museum, and enjoy the charm of urban parks and historic buildings. Whether you're wandering through historic houses or enjoying the picturesque scenery, Chesterfield promises an enriching getaway for everyone.

  • Chatsworth House: Nestled 12.9km from Chesterfield, Chatsworth House is a magnificent historic estate renowned for its stunning architecture and exquisite gardens. Visitors can immerse themselves in rich cultural heritage while exploring opulent rooms filled with art and antiques.
  • Bolsover Castle: Located within Chesterfield, Bolsover Castle offers a romantic glimpse into the past with its impressive ruins and enchanting gardens. The castle's fascinating history and beautiful views make it a perfect spot for leisurely exploration.
  • Hardwick Hall: Situated in Chesterfield, Hardwick Hall is a remarkable historic building famed for its striking Elizabethan architecture. Visitors can enjoy its beautifully designed interiors and learn about the intriguing stories behind its creation.

Best time to go to Chesterfield

The best time to visit Chesterfield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly cloudy with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.3°F (3.5°C)Light RainMostly CloudyAverageSlightly Low
February39.4°F (4.1°C)No RainMostly CloudyAverageSlightly Low
March42.3°F (5.7°C)No RainMostly CloudyAverageSlightly Low
April46.2°F (7.9°C)No RainMostly CloudySlightly HighSlightly High
May51.8°F (11.0°C)Light RainMostly CloudyAverageAverage
June57.2°F (14.0°C)Light RainMostly CloudyAverageSlightly High
July60.8°F (16.0°C)Light RainMostly CloudySlightly HighSlightly High
August60.3°F (15.7°C)Light RainMostly CloudyAverageAverage
September56.5°F (13.6°C)No RainMostly CloudySlightly HighAverage
October50.7°F (10.4°C)Light RainMostly CloudySlightly LowAverage
November44.1°F (6.7°C)Light RainMostly CloudySlightly LowAverage
December40.1°F (4.5°C)Light RainMostly CloudySlightly LowAverage

Tips to save on your trip to Chesterfield

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chesterfield.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Chesterfield.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Chesterfield Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
East Midlands Airport (EMA)
Population
113,100
Max Temp Winter
7ºC
Max Temp Summer
18ºC
Top Sights
Bolsover Castle, Hotel Van Dyk Theatre and Barrow Hill Roundhouse Railway Centre

Top hotels in Chesterfield

WILDES INNS

WILDES INNS

Worksop Road Chesterfield England
Fully refundableReserve now, pay when you stay
£69
29 Sept - 30 Sept
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"Window was broken and couldn't close it. Toilet seat was loose and wobbly. Lamps didnt work in the room. Luckily we wasn't in the room long as we were just there for a wedding."

Reviewed on 18 Sept 2026

WILDES INNS
Ringwood Hall Hotel & Spa, BW Signature Collection

Ringwood Hall Hotel & Spa, BW Signature Collection

Chesterfield Road Chesterfield England
Fully refundableReserve now, pay when you stay
£77
4 Oct - 5 Oct
includes taxes & fees
8/10 Very good! (1,000 reviews)
"We were put in a separate lodge to the main hotel which was a bit of a walk away from the main building over a fairly rough path. The room was clean and well kept, the bathroom had a large two seater bath with a separate shower. The shower though had no where to put and soap or bottles, could have ..."

Reviewed on 16 Sept 2026

Ringwood Hall Hotel & Spa, BW Signature Collection
Garner Hotel Chesterfield North by IHG

Garner Hotel Chesterfield North by IHG

3 Tallys End Chesterfield England
Fully refundable
£42
4 Oct - 5 Oct
includes taxes & fees
Garner Hotel Chesterfield North by IHG
See all 5,811 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.

The Advantages of Chesterfield Weekend Breaks

Discover a different side of the British Isles with a weekend break in Chesterfield. Take short breaks away from home and enjoy some quality time in a beautiful place. You’ll come back feeling refreshed and inspired. You can have an action-packed Chesterfield weekend break or get some peace with a relaxing holiday. Whatever experience you’re looking for, find it with our deals on hotels in Chesterfield.

Cheap Weekend Breaks to Chesterfield

There are lots of ways to take cheap weekend breaks to Chesterfield. Expedia offers deals on car hires and hotel rooms and covers trips for all kinds of travellers. The best way to save is with our holiday packages in Chesterfield. First, choose your car hire and hotel reservation. Then we’ll bundle them together into one discounted price. Solo explorers, couples, families, and groups of friends can discover budget solutions for their weekend breaks. Once you arrive, enjoy some of the fun things to do, many of which are free or cheap to experience  

Chesterfield Romantic Weekend Breaks

Couples love taking romantic weekend breaks in Chesterfield. Whisking your lover away for a romantic Chesterfield weekend break is the perfect opportunity to make new memories together. Expedia offers all kinds of hotel options, so you can find romantic hotels in Chesterfield and choose the best place for you. Check out our deals on beautiful properties, and you’ll save even more when you choose to package your hotel reservation with a car hire.

Family Weekend Breaks in Chesterfield

Set some time aside to experience family weekend breaks in Chesterfield. There are plenty of excellent family-friendly hotels in Chesterfield within our selection of hotels. You can also find a place to call home in one of the holiday rentals in Chesterfield. With accommodation, activities, and adventure all waiting, there’s never been a better time to plan Chesterfield family weekend breaks.

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

Stay near popular Chesterfield attractions

A historic castle with stone walls, multiple towers, and a set of stone steps leading up to the entrance.
Photo by Barbara Croft

Bolsover Castle

9.6/10 (22 reviews)
You can find out about the history of Bolsover with a stop at Bolsover Castle. Visit the spas and lively bars in this relaxing area.
See properties
A large, historic building with multiple windows and a prominent entrance.
Photo by Phil Betesta

Hardwick Hall

9.6/10 (45 reviews)
You can find out about the history of Ault Hucknall when you stop by Hardwick Hall. Visit the lively bars or top-notch restaurants in this relaxing area.
See properties

Chesterfield Market

8.4/10 (29 reviews)
You can do some window-shopping at Chesterfield Market during your visit to Chesterfield. Visit the spas and lively bars in this culturally rich area.
See properties

Queen's Park

9.0/10 (10 reviews)
Explore the great outdoors at Queen's Park, a lovely green space in Chesterfield. Visit the spas and lively bars in this family-friendly area.
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Barrow Hill Roundhouse Railway Centre

9.0/10 (4 reviews)
You can spend an afternoon browsing the exhibits at Barrow Hill Roundhouse Railway Centre in Brimington. Make time to visit the area's spas or simply enjoy its lively bars.
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Hotel Van Dyk Theater

8.8/10 (3 reviews)
You can get tickets for a performance at Hotel Van Dyk Theater during your stay in Clowne. Visit the spas and top-notch restaurants in this relaxing area.
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Poolsbrook Country Park

10.0/10 (1 review)
Explore the great outdoors at Poolsbrook Country Park, a lovely green space in Staveley. Visit the spas and lively bars in this relaxing area.
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SMH Group Stadium

Catch an event at SMH Group Stadium during your trip to Chesterfield. Savour the top-notch restaurants and lively bars while in town.
See properties

What to do in Chesterfield

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

Idyllic England: Derbyshire & the Peak District from Manchester

£74
per adult
90% of travellers recommend
Idyllic England: Derbyshire & the Peak District from Manchester
A fun and different way to see Sheffield

Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems

£15
per adult
Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems
Lost in Beauty: Chatsworth & Peak District from Manchester

Lost in Beauty: Chatsworth & Peak District from Manchester

£119
per adult
Lost in Beauty: Chatsworth & Peak District from Manchester
See all activities in Chesterfield

Frequently asked questions

Why should I book my Chesterfield holiday with Expedia?
With exceptional-value airfares, hotel and car hire options all in one place, Expedia makes arranging your Chesterfield getaway a cinch. Plus, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Choose from fantastic properties, add flights and/or a hire car (and maybe also some exciting activities!) and get incredible prices. Need to change your plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, head over to our Customer Service Portal link.
When is the best time of year to holiday in Chesterfield?
Love sightseeing but don't like crowds? Lock in your Chesterfield getaway for May, July and December. Typically, it's a lot quieter than in February, March and June. Organise your trip to Chesterfield according to what type of holiday you're looking for. January is the coolest time of year, when average daytime temperatures are 3ºC. In July, the warmest month, you'll experience averages of 16ºC during the day.
What are the top hotels for my holiday in Chesterfield?
Many visitors to Chesterfield often stay in Tupton. ibis Chesterfield North - Barlborough and ibis Chesterfield Centre – Market Town are popular options in this neighbourhood. But it's not the only exciting place in town! Wingerworth is another fantastic area and where you'll find Van Dyk by Wildes and Casa Hotel.
How do I get a cheap holiday to Chesterfield?
Bundle your bookings with Expedia to save on your next getaway. With over 400 partner airlines and 321,000 hotels across the globe, your Chesterfield holiday can be tailored exactly to suit your budget. With all those extra pounds, why not throw in a few awesome activities and tours? It's an easy way to unlock even more bargains. Your dream getaway to Chesterfield is closer than you thought! Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Chesterfield holiday?
There are lots of places to check out while on your holiday in Chesterfield. Chatsworth House, Bolsover Castle, Hardwick Hall and Chatsworth House Labyrinth are a few of this city's top attractions.
What is the best area to stay in when on holiday in Chesterfield?
If you plan to check out Bolsover Castle, save yourself the hassle of commuting and lock in a stay nearby. It's one of the best attractions in Chesterfield.
Do I need a visa for my Chesterfield holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and reason for your visit, whether it be for tourism or work, will determine if you'll need a visa for Chesterfield. Also double-check that your passport is up to date and has a minimum of six months validity remaining beyond the date of your return. Finalise all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Chesterfield holiday?
Do some research into the types of clothing people in Chesterfield wear, and consider browsing social media fashion pages for inspiration. You'll want to create a versatile wardrobe with pieces that work for your destination and showcase your unique style. Pack your luggage with confidence by checking the local weather conditions in Chesterfield. July brings the warmest temperatures, with daytime averages of 16ºC, while January days average 3ºC, making it the coolest month.
What does an Expedia Chesterfield holiday include?
Expedia has everything you need to plan your Chesterfield getaway, but how your package is structured is up to you. Choose from any combination of flights, hotels and hire cars. Looking for some activities or tours to fill in your time? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a holiday package to suit your needs. Discover a wide range of property types and pick one that fits your group size and travel needs. The most in-demand holiday rentals here are cottages and private holiday homes. With Expedia, it's easy to tailor your Chesterfield retreat just the way you like.
Does Expedia offer Book Now, Pay Later Chesterfield holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Consider one of these flexible payment options:
  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's easy instalment plans. If paying just a small amount each month sounds right for you, choose this option during the checkout process.
  • No-deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.
Can I choose my airline with a Chesterfield Expedia holiday?
Yes, and with over 400 airlines to select from worldwide, you're not short on choice. Have a look through the available options and see which airline best fits your budget and needs.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.