Title: Chester Holidays 2025 from $395 | Expedia.co.uk [Hotels in Chester](https://expedia.co.uk/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Holiday Rentals in Chester](https://expedia.co.uk/Chester-Holiday-Rentals.d6005399.Travel-Guide-HolidayRentals)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d6005399.Car-Hire-Guide) ![](https://images.trvl-media.com/place/6005399/400cb5cc-e1d2-4765-9a2f-8870b6e8f711.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester Holidays ## Book a Hotel + Flight or Car together to unlock savings Photo by Elizabeth Massa Peroulakis - ## 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 Chester Holiday Our holiday packages to Chester allow you to create your own adventure. Tailor your getaway to your needs and interests and make every moment count in this fantastic city. There's a whole load to see during a trip to Chester, including [Becket Land Trust Historic Quarry](https://www.expedia.co.uk/Becket-Land-Trust-Historic-Quarry-Becket.d553248621532666600.Attraction) and [Chester Town Hall](https://www.expedia.co.uk/Chester-Town-Hall-Chester.d553248621532666604.Attraction). Check out Expedia's wide range of travel options and book your ultimate holiday to Chester today. ## Chester Essential Information | Language | English | | --- | --- | | Currency | U.S dollars | | Closest Airport | Bradley Intl. Airport (BDL) | | Population | 630 | | Max Temp Winter | \\-1.11ºC | | Max Temp Summer | 24ºC | | Top Sights | [Blandford Ski Area](https://www.expedia.co.uk/Blandford-Ski-Area-Blandford.d553248621532666606.Attraction), [Maple Corner Farm Cross Country Ski Area](https://www.expedia.co.uk/Maple-Corner-Farm-Cross-Country-Ski-Area-Granville.d553248621532666041.Attraction) and [Chester Town Hall](https://www.expedia.co.uk/Chester-Town-Hall-Chester.d553248621532666604.Attraction) | ## Top hotels in Chester ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr, Pittsfield, MA Fully refundableReserve now, pay when you stay £93 21 Sept - 22 Sept includes taxes & fees 8.8/10 Excellent! (646 reviews) "Excellent location. Friendly staff." Reviewed on 17 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F09%2F2025&endDate=22%2F09%2F2025&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6005399) ![La Quinta Inn & Suites by Wyndham Springfield MA](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Springfield MA 100 Congress Street, Springfield, MA Fully refundableReserve now, pay when you stay £100 19 Oct - 20 Oct includes taxes & fees 8/10 Very Good! (1,265 reviews) "Overall a great stay for a quick business overnight. Downfall was the shower head in bathroom had extremely low water pressure (basically non existent) and made a horrible clunking noise. Perhaps the mixing valve was broken. Found this out in morning of." Reviewed on 16 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=18056&PinnedHotelID=18056&HadPinnedHotel=true®ionId=6005399) ![Red Roof Inn PLUS+ West Springfield](https://images.trvl-media.com/lodging/1000000/30000/27100/27090/23b7c14f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Red Roof Inn PLUS+ West Springfield 1254 Riverdale Street, West Springfield, MA Fully refundableReserve now, pay when you stay £75 5 Oct - 6 Oct includes taxes & fees 6.8/10 (1,013 reviews) "Excellent overall!" Reviewed on 13 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=27090&PinnedHotelID=27090&HadPinnedHotel=true®ionId=6005399) [See all 830 properties in Chester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F09%2F2025&endDate=22%2F09%2F2025®ionId=6005399) 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) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes ### Accommodation - [3 Star Hotels in The Berkshires](https://www.expedia.co.uk/3Star-The-Berkshires-Hotels.s30-0-d6047665.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Berkshires](https://www.expedia.co.uk/4Star-The-Berkshires-Hotels.s40-0-d6047665.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Western Massachusetts](https://www.expedia.co.uk/4Star-Western-Massachusetts-Hotels.s40-0-d6234063.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Worthington](https://www.expedia.co.uk/5Star-Worthington-Hotels.s50-0-d6005428.Travel-Guide-Filter-Hotels) - [Becket Hotels](https://www.expedia.co.uk/Becket-Hotels.d6005395.Travel-Guide-Hotels) - [Blandford Hotels](https://www.expedia.co.uk/Blandford-Hotels.d80625.Travel-Guide-Hotels) - [Chesterfield Hotels](https://www.expedia.co.uk/Chesterfield-Hotels.d89029.Travel-Guide-Hotels) - [Huntington Hotels](https://www.expedia.co.uk/Huntington-Hotels.d6005407.Travel-Guide-Hotels) - [Hotels near Jacob's Pillow](https://www.expedia.co.uk/Jacobs-Pillow-Hotels.0-l553248621532666599-0.Travel-Guide-Filter-Hotels) - 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[Flights from Russell](https://www.expedia.co.uk/lp/flights/6005415/flights-from-russell) - [Flights from Western Massachusetts](https://www.expedia.co.uk/lp/flights/6234063/flights-from-western-massachusetts) ### Packages - [Ashfield Lake](https://www.expedia.co.uk/Ashfield-Lake-Ashfield.d553248621532666614.Attraction) - [Ashuwillticook Rail Trail Holidays](https://www.expedia.co.uk/Ashuwillticook-Rail-Trail.d811531152953708544.Holidays-City-Breaks) - [Visit Becket](https://www.expedia.co.uk/Becket.dx6005395) - [Blandford Ski Area](https://www.expedia.co.uk/Blandford-Ski-Area-Blandford.d553248621532666606.Attraction) - [Visit Blandford](https://www.expedia.co.uk/Blandford.dx80625) - [Chesterfield Gorge](https://www.expedia.co.uk/Chesterfield-Gorge-Chesterfield.d553248621532666609.Attraction) - [Conway Holidays](https://www.expedia.co.uk/Conway.d6285365.Holidays-City-Breaks) - [Cummington Holidays](https://www.expedia.co.uk/Cummington.d183324.Holidays-City-Breaks) - [Granville Holidays](https://www.expedia.co.uk/Granville.d6005404.Holidays-City-Breaks) - [Great Barrington Holidays](https://www.expedia.co.uk/Great-Barrington.d110336.Holidays-City-Breaks) - [Hoffman's Pottery](https://www.expedia.co.uk/Hoffmans-Pottery-West-Stockbridge.d553248621532665251.Attraction) - [Housatonic River Walk](https://www.expedia.co.uk/Housatonic-River-Walk-Great-Barrington.d553248621532665241.Attraction) - [Housatonic Holidays](https://www.expedia.co.uk/Housatonic.d3000441135.Holidays-City-Breaks) - [Lake Mansfield Park](https://www.expedia.co.uk/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Attraction) - [Lanesborough Holidays](https://www.expedia.co.uk/Lanesborough.d6005408.Holidays-City-Breaks) - [Lenox Holidays](https://www.expedia.co.uk/Lenox.d8587.Holidays-City-Breaks) - [Magnolia Bluffs Casino](https://www.expedia.co.uk/Magnolia-Bluffs-Casino-Sheffield.d553248621532644877.Attraction) - [Monterey Holidays](https://www.expedia.co.uk/Monterey.d6005411.Holidays-City-Breaks) - [Norman Rockwell Museum](https://www.expedia.co.uk/Norman-Rockwell-Museum-Stockbridge.d6091839.Attraction) - [Otis Holidays](https://www.expedia.co.uk/Otis.d6005412.Holidays-City-Breaks) - [Russell Holidays](https://www.expedia.co.uk/Russell.d6005415.Holidays-City-Breaks) - [Savoy Holidays](https://www.expedia.co.uk/Savoy.d6005417.Holidays-City-Breaks) - [South Deerfield Holidays](https://www.expedia.co.uk/South-Deerfield.d159873.Holidays-City-Breaks) - [Southampton Holidays](https://www.expedia.co.uk/Southampton.d6005419.Holidays-City-Breaks) - [Southfield Holidays](https://www.expedia.co.uk/Southfield.d6339785.Holidays-City-Breaks) - [Swift River](https://www.expedia.co.uk/Swift-River-Massachusetts.d681613380051832832.Attraction) - [Tanglewood Music Center](https://www.expedia.co.uk/Tanglewood-Music-Center-Lenox.d503292.Attraction) - [The Berkshires Holidays](https://www.expedia.co.uk/The-Berkshires.d6047665.Holidays-City-Breaks) - [Visit The Berkshires](https://www.expedia.co.uk/The-Berkshires.dx6047665) - [Ventfort Hall Mansion and Gilded Age Museum](https://www.expedia.co.uk/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Attraction) - [Western Massachusetts Holidays](https://www.expedia.co.uk/Western-Massachusetts.d6234063.Holidays-City-Breaks) - [Visit Western Massachusetts](https://www.expedia.co.uk/Western-Massachusetts.dx6234063) - [Westfield Holidays](https://www.expedia.co.uk/Westfield.d10439.Holidays-City-Breaks) - [Windsor Holidays](https://www.expedia.co.uk/Windsor.d6005427.Holidays-City-Breaks) ### Cars - [Car hire near The Berkshires](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-The-Berkshires.d6047665.Car-Hire-Guide) ### Holiday Homes - [Becket Holiday Rentals](https://www.expedia.co.uk/Becket-Holiday-Rentals.d6005395.Travel-Guide-HolidayRentals) - [Peru Holiday Rentals](https://www.expedia.co.uk/Peru-Holiday-Rentals.d553248634999167831.Travel-Guide-HolidayRentals) - [The Berkshires Holiday Rentals](https://www.expedia.co.uk/The-Berkshires-Holiday-Rentals.d6047665.Travel-Guide-HolidayRentals) - [Western Massachusetts Holiday Rentals](https://www.expedia.co.uk/Western-Massachusetts-Holiday-Rentals.d6234063.Travel-Guide-HolidayRentals) \* 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 ![QR code to download the app](data:image/png;base64,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)