Chesterfield Holidays from £147

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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.
Holiday Inn Ellesmere Port by IHG
Bennetts Hotel
Delta Hotels Worsley Park Country Club
INNSiDE by Meliá Manchester

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.

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

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 £73 per night from 1 Mar to 2 Mar
£73
1 Mar - 2 Mar
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Staff friendliness

Reviewed on 28 Jan 2026

Ringwood Hall Hotel & Spa
WILDES INNS

WILDES INNS

4 out of 5
Worksop Road Chesterfield England
Fully refundableReserve now, pay when you stay
The price is £80 per night from 22 Feb to 23 Feb
£80
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Room was nice and clean and bed was comfortable. All the staff were nice and helpful and breakfast was good (plenty of choice)

Reviewed on 8 Feb 2026

WILDES INNS
Twin Oaks Hotel

Twin Oaks Hotel

3 out of 5
Church Lane Chesterfield England
The price is £62 per night from 15 Feb to 16 Feb
£62
15 Feb - 16 Feb
includes taxes & fees
8.6/10 Excellent! (441 reviews)
Clean room and bathroom. Comfy bed. Shame there is no heating in the bathroom, as very cold when showering. Tv is a bit old. Staff are nice and food is very good.

Reviewed on 25 Jan 2026

Twin Oaks Hotel
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.

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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. Flight-inclusive packages are ATOL protected.