Title: Chesterfield Vacation Packages & Trips 2026 from CA $1,311 | Expedia.ca [Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d4599.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d4599.Travel-Guide-VacationRentals)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d4599.Car-Rental-Guide) ![](https://images.trvl-media.com/place/4599/a72e522b-c47a-4a9e-a5b6-fbb0d4a35b67.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesterfield Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Bolsover-Castle-Chesterfield.d6162892.Vacation-Attraction), [Chesterfield Market](https://www.expedia.ca/Chesterfield-Market-Chesterfield.d6162900.Vacation-Attraction) and [Barrow Hill Roundhouse Railway Centre](https://www.expedia.ca/Barrow-Hill-Roundhouse-Railway-Centre-Chesterfield.d553248621532493112.Vacation-Attraction) 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. ![Holiday Inn Express Manchester City Centre Arena by IHG](https://images.trvl-media.com/lodging/5000000/4520000/4513300/4513278/23351fb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Manchester City Centre Arena by IHG Manchester City Centre CA $1,311 per person Feb 25 - Mar 2 found 7 hours ago Roundtrip flight included Montreal (YUL) to Manchester (MAN) 8.6/10 Excellent! (1,122 reviews) Friendly staff, clean room, only down side tables to close together for breakfast, Reviewed on Dec 14, 2025 ![Opfa Property](https://images.trvl-media.com/lodging/122000000/121830000/121825100/121825077/ec7a2e7f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Opfa Property CA $2,697 per person Feb 26 - Mar 2 found 7 hours ago Roundtrip flight included Montreal (YUL) to Manchester (MAN) No reviews ![Manchester High St](https://images.trvl-media.com/lodging/123000000/122730000/122720600/122720583/d35f0980_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Manchester High St Manchester City Centre CA $1,522 per person Feb 25 - Mar 2 found 7 hours ago Roundtrip flight included Montreal (YUL) to Manchester (MAN) No reviews ![Manchester Portland By Sunday](https://images.trvl-media.com/lodging/1000000/20000/19400/19309/47c1cb25_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Manchester Portland By Sunday Manchester City Centre CA $1,408 per person Feb 25 - Mar 2 found 7 hours ago Roundtrip flight included Montreal (YUL) to Manchester (MAN) 8.4/10 Very Good! (1,445 reviews) Very nice staff. Don't use the laundry service - too expensive. Room was warm because you set it yourself. Reviewed on Dec 9, 2025 ![DoubleTree by Hilton Manchester - Piccadilly](https://images.trvl-media.com/lodging/2000000/1680000/1671600/1671525/fa6419fb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Manchester - Piccadilly Manchester City Centre CA $1,661 per person Feb 25 - Mar 2 found 7 hours ago Roundtrip flight included Montreal (YUL) to Manchester (MAN) 9/10 Wonderful! (1,002 reviews) Our room was very clean and comfortable and the staff was amazing. Reviewed on Dec 14, 2025 ## Ready to book your vacation to Chesterfield? Choose your dates ## Chesterfield Hotel Deals ![Ringwood Hall Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/28100/28073/bd05248f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ringwood Hall Hotel & Spa Chesterfield Road Chesterfield England Fully refundableReserve now, pay when you stay CA $127 CA $153 total Jan 7 - Jan 8, 2026 includes taxes & fees 8/10 Very Good! (988 reviews) Bed was extremely comfortable and quiet and warm room but the carpet in the disabled room 117 was in need of renewing dirty marks and did not feel clean.the shower head and attachment were broken and hence I had a bad shower.the exit from this part of the building was not lit up well and i found ... Reviewed on Dec 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=28073&PinnedHotelID=28073&HadPinnedHotel=true®ionId=4599) ![WILDES INNS](https://images.trvl-media.com/lodging/4000000/3750000/3748600/3748598/d7bf94b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### WILDES INNS Worksop Road Chesterfield England Fully refundableReserve now, pay when you stay 8.6/10 Excellent! (1,002 reviews) Great hotel will stop again Reviewed on Dec 11, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=3748598&PinnedHotelID=3748598&HadPinnedHotel=true®ionId=4599) [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=3748598&PinnedHotelID=3748598&HadPinnedHotel=true®ionId=4599) ![Olde House, Chesterfield by Marston's Inns](https://images.trvl-media.com/lodging/34000000/33110000/33108600/33108591/74745ec5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Olde House, Chesterfield by Marston's Inns Loundsley Green Rd Chesterfield England Fully refundableReserve now, pay when you stay 9/10 Wonderful! (321 reviews) Suited our needs perfectly Reviewed on Dec 8, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=33108591&PinnedHotelID=33108591&HadPinnedHotel=true®ionId=4599) [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=33108591&PinnedHotelID=33108591&HadPinnedHotel=true®ionId=4599) [See all 5,253 properties in Chesterfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=4599) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### What to do in Chesterfield ![Small-Group Derbyshire, the Peak District & Poole's Cavern](https://mediaim.expedia.com/localexpert/2220906/369785c6-a2cb-4504-9a08-cbb33bf86144.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Idyllic England: Derbyshire & the Peak District from Manchester CA $102 per adult **90%** of travellers recommend [](https://expedia.ca/things-to-do/idyllic-england-derbyshire-the-peak-district-from-manchester.a2220906.activity-details) ![A fun and different way to see Sheffield](https://mediaim.expedia.com/localexpert/5248401/65504be5-a0b6-4f9b-8d60-389337f3d207.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fun, Flexible Treasure Hunt Around Sheffield with Cryptic Clues & Hidden Gems CA $28 per adult [](https://expedia.ca/things-to-do/fun.a5248401.activity-details) ![Bar and Club entry Night Pass to multiple venues in Sheffield](https://mediaim.expedia.com/localexpert/45072796/b3e11c46-04fc-4b54-b5cc-f3c07b569f03.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bar and Club entry Night Pass to multiple venues in Sheffield CA $18 per adult [](https://expedia.ca/things-to-do/bar-and-club-entry-night-pass-to-multiple-venues-in-sheffield.a45072796.activity-details) [See all activities in Chesterfield](https://expedia.ca/things-to-do/search?rid=4599) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app