Title: Chesterfield Holidays 2026 from £998 | Expedia.co.uk [Hotels in Chesterfield](https://expedia.co.uk/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Holiday Rentals in Chesterfield](https://expedia.co.uk/Chesterfield-Holiday-Rentals.d89029.Travel-Guide-HolidayRentals)[Chesterfield Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chesterfield.d89029.Car-Hire-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesterfield Holidays from £998 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected #### Your Chesterfield Holiday Skip the stress of organising your next big adventure with a Chesterfield holiday package. Whether you're in town for its art, food, architecture or something else, this city offers countless exciting experiences to delve into. A trip to Chesterfield is an excellent opportunity to take in the sights. Check out renowned attractions like [Chesterfield Gorge](https://www.expedia.co.uk/Chesterfield-Gorge-Chesterfield.d553248621532666609.Attraction), [Swift River](https://www.expedia.co.uk/Swift-River-Massachusetts.d681613380051832832.Attraction) and [Petticoat Hill](https://www.expedia.co.uk/Petticoat-Hill-Williamsburg.d553248621532666673.Attraction). Your perfect Chesterfield holiday is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your style. ## Top Chesterfield Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Boston North Shore](https://images.trvl-media.com/lodging/1000000/20000/15400/15355/46b6ba4c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Boston North Shore £998 per person 8 Jun - 15 Jun found 22 hours ago Return flight included London (LHR) to Boston (BOS) 8.2/10 Very Good! (2,401 reviews) Clean room, friendly staff Reviewed on 4 Apr 2026 ![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/ee935931_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars The Boxer West End Save 100% on your flight £1,873 per person 25 Jun - 30 Jun found 1 day ago Return direct flight included Birmingham (BHX) to Boston (BOS) 8.8/10 Excellent! (1,426 reviews) Location, location, location! Breakfast is top notch. The entire staff was helpful and friendly. Reviewed on 3 Apr 2026 ![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Hastings Park, Relais & Chateaux - Boston Save 100% on your flight £1,409 per person 20 Jun - 25 Jun found 1 day ago Return flight included London (LHR) to Boston (BOS) 9.6/10 Exceptional! (252 reviews) Excellent experience- clean and very helpful staff Reviewed on 9 Mar 2026 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f081d391_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay Save 100% on your flight £2,580 per person 25 Jun - 30 Jun found 1 day ago Return direct flight included Birmingham (BHX) to Boston (BOS) 9.6/10 Exceptional! (248 reviews) The photos doesn’t give this place justice. Reviewed on 24 Mar 2026 ![Hyatt Regency Boston/Cambridge](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/944dfde2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Boston/Cambridge MIT £1,290 per person 8 Jun - 15 Jun found 22 hours ago Return flight included London (LHR) to Boston (BOS) 9/10 Wonderful! (2,275 reviews) Beautiful state of the art hotel... staff was great, room was nice, even great TV.... can't wait to return here Reviewed on 6 Apr 2026 ## Chesterfield Essential Information | Language | English | | --------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 1,200 | | Max Temp Winter | 2ºC | | Max Temp Summer | 27ºC | | Top Sights | [Academy of Music Theatre](https://www.expedia.co.uk/Academy-Of-Music-Theater-Northampton.d6070271.Attraction), [Historic Northampton](https://www.expedia.co.uk/Historic-Northampton-Northampton.d553248621532666662.Attraction) and [Calvin Theatre](https://www.expedia.co.uk/Calvin-Theater-Northampton.d6213809.Attraction) | ## Top hotels in Chesterfield ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### D. Hotel Suites & Spa 1 Country Club Rd Holyoke MA Fully refundableReserve now, pay when you stay £108 21 Apr - 22 Apr includes taxes & fees 9.4/10 Exceptional! (2,228 reviews) ❤️ Reviewed on 6 Apr 2026 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F04%2F2026&endDate=22%2F04%2F2026&selected=849303&PinnedHotelID=849303&HadPinnedHotel=true®ionId=89029) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundableReserve now, pay when you stay £90 6 May - 7 May includes taxes & fees 9/10 Wonderful! (895 reviews) Love that place. Does need a little sprucing up. Staff great and accomodating Reviewed on 5 Apr 2026 [](https://expedia.co.uk/Hotel-Search?startDate=06%2F05%2F2026&endDate=07%2F05%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=89029) ![Comfort Inn & Suites Hadley - Amherst](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/f0e51cc3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Hadley - Amherst 400 Russell St Hadley MA Fully refundable £113 14 Apr - 15 Apr includes taxes & fees 9.2/10 Wonderful! (1,009 reviews) Excellent breakfast for a quick unexpected benefit Reviewed on 5 Apr 2026 [](https://expedia.co.uk/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=558078&PinnedHotelID=558078&HadPinnedHotel=true®ionId=89029) [See all 515 properties in Chesterfield](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F04%2F2026&endDate=08%2F04%2F2026®ionId=89029) 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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Popular places to visit #### Chesterfield Gorge Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area. [](https://expedia.co.uk/Chesterfield-Gorge-Chesterfield.d553248621532666609.Attraction) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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