Title: Cheshire Travel Guide: Best of Cheshire, Massachusetts Travel 2025 | Expedia.co.uk [Hotels in Cheshire](https://expedia.co.uk/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Holiday Rentals in Cheshire](https://expedia.co.uk/Cheshire-Holiday-Rentals.d6005398.Travel-Guide-HolidayRentals)[Flights to Cheshire](https://expedia.co.uk/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Cheshire Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Cheshire.d6005398.Car-Hire-Guide)[Cheshire Holidays](https://expedia.co.uk/Cheshire.d6005398.Holidays-City-Breaks) # Cheshire Travel Guide ## Tourist Guide ![Photo by Ed Gaffny](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Ed Gaffny](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg) ![Photo by Chris Addams](https://mediaim.expedia.com/destination/2/fa88c56ac508d2b7e0956184ee96b6cf.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Chris Addams](https://mediaim.expedia.com/destination/2/fa88c56ac508d2b7e0956184ee96b6cf.jpg) ![Photo by Chris Addams](https://mediaim.expedia.com/destination/2/fca6f90b8c90b2ba024338672184667a.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Chris Addams](https://mediaim.expedia.com/destination/2/fca6f90b8c90b2ba024338672184667a.jpg) ![Photo by Chris Addams](https://mediaim.expedia.com/destination/2/53a79e170bf1208fd67dbef187d0ba8f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Chris Addams](https://mediaim.expedia.com/destination/2/53a79e170bf1208fd67dbef187d0ba8f.jpg) ![Photo by Chris Addams](https://mediaim.expedia.com/destination/2/0bbeb5c343ebcf670623da277b2a855b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Chris Addams](https://mediaim.expedia.com/destination/2/0bbeb5c343ebcf670623da277b2a855b.jpg) ## Visit Cheshire Things to do - Top hotels in Cheshire - Top Holiday Rentals in Cheshire ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd, Williamstown, MA £94 28 Sept - 29 Sept includes taxes & fees Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,006 reviews) "Quiet, clean, beautifully landscaped- such a comfy bed!" Reviewed on 13 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=6005398) ![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 £94 28 Sept - 29 Sept includes taxes & fees Stay at this 3-star golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ... 8.8/10 Excellent! (646 reviews) "Excellent location. Friendly staff." Reviewed on 17 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6005398) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 190 Meadow Street, South Lee, MA £114 28 Sept - 29 Sept includes taxes & fees Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business centre and a snack bar/deli. Our guests praise the helpful staff ... 9/10 Wonderful! (733 reviews) "What a gem!" Reviewed on 20 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=20875006&PinnedHotelID=20875006&HadPinnedHotel=true®ionId=6005398) [See all 997 properties in Cheshire](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=26%2F09%2F2025&endDate=27%2F09%2F2025®ionId=6005398) 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. ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd, Williamstown, MA Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,006 reviews) "Quiet, clean, beautifully landscaped- such a comfy bed!" Reviewed on 13 Sept 2025 [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jiminy Peak Mountain Resort 37 Corey Rd, Hancock, MA Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular ... 8.2/10 Very Good! (977 reviews) "Absolutely beautiful" Reviewed on 17 Sept 2025 [](https://expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Huttopia Berkshires 312 Kittle Rd, Williamstown, MA Stay at this campsite in Williamstown. Enjoy free parking, breakfast (surcharge) and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ... 10/10 Exceptional! (4 reviews) "Great Time! Beautiful new tents with all the items you need to Glamp with from silverware to tupperware. Comfy beds and comforter! Everyone was so nice and you know they love what they do! Next fall/foiliage camping in the trapper with the wood stove !" Reviewed on 25 Aug 2025 [](https://expedia.co.uk/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) [See all properties in Cheshire](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6005398&sort=VACATION_RENTAL) 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. ## Check Cheshire hotel availability [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-25&endDate=2025-09-26) [Tonight](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-25&endDate=2025-09-26) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-25&endDate=2025-09-26) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-25&endDate=2025-09-26)[25 Sept - 26 Sept](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-25&endDate=2025-09-26) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-26&endDate=2025-09-27) [Tomorrow night](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-26&endDate=2025-09-27) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-26&endDate=2025-09-27) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-26&endDate=2025-09-27)[26 Sept - 27 Sept](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-09-26&endDate=2025-09-27) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025) [This weekend](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025)[26 Sept - 28 Sept](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=26%2F09%2F2025&endDate=28%2F09%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [Next weekend](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025)[3 Oct - 5 Oct](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) ### Popular places to visit #### St Mary's of the Assumption Church St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views or seek out its ski slopes. [](https://expedia.co.uk/St-Marys-Of-The-Assumption-Church-Cheshire.d553248621532665539.Attraction) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - [Adams Hotels](https://www.expedia.co.uk/Adams-Hotels.d6005393.Travel-Guide-Hotels) - [Guest Houses in Ashuwillticook Rail Trail](https://www.expedia.co.uk/Ashuwillticook-Rail-Trail-Guest-Houses.d811531152953708544-aaGuestHouses.Travel-Guide-Accommodation) - [Cummington Hotels](https://www.expedia.co.uk/Cummington-Hotels.d183324.Travel-Guide-Hotels) - [Dalton Hotels](https://www.expedia.co.uk/Dalton-Hotels.d6911.Travel-Guide-Hotels) - [Berkshire County Hotels](https://www.expedia.co.uk/Destinations-In-Berkshire-County.d553248635083901436.Hotel-Destinations) - [Drury Hotels](https://www.expedia.co.uk/Drury-Hotels.d3000748865.Travel-Guide-Hotels) - [Florida Hotels](https://www.expedia.co.uk/Florida-Hotels.d553248634999031091.Travel-Guide-Hotels) - [Hancock Hotels](https://www.expedia.co.uk/Hancock-Hotels.d112303.Travel-Guide-Hotels) - 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[Hotels with Indoor Pools in Lenox](https://www.expedia.co.uk/Lenox-Hotels-Hotels-With-Indoor-Pools.0-0-d8587-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Lenox](https://www.expedia.co.uk/Lenox-Hotels-Luxury-Hotel.0-0-d8587-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Lenox Hotels](https://www.expedia.co.uk/Lenox-Hotels.d8587.Travel-Guide-Hotels) - [Hotels near Mount Greylock](https://www.expedia.co.uk/Mount-Greylock-Hotels.0-l6091829-0.Travel-Guide-Filter-Hotels) - [New Ashford Hotels](https://www.expedia.co.uk/New-Ashford-Hotels.d183333.Travel-Guide-Hotels) - [North Adams Hotels](https://www.expedia.co.uk/North-Adams-Hotels.d9137.Travel-Guide-Hotels) - [Lodges in October Mountain State Forest](https://www.expedia.co.uk/October-Mountain-State-Forest-Lodges.d6339856-aaLodges.Travel-Guide-Accommodation) - [Peru Hotels](https://www.expedia.co.uk/Peru-Hotels.d553248634999167831.Travel-Guide-Hotels) - [Cheap Hotels in Pittsfield](https://www.expedia.co.uk/Pittsfield-Hotels-Budget-Hotels.0-0-d9478-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Pittsfield Hotels](https://www.expedia.co.uk/Pittsfield-Hotels.d9478.Travel-Guide-Hotels) - [B&B in Savoy](https://www.expedia.co.uk/Savoy-Bed-And-Breakfasts.d6005417-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [Hilton Hotels in Savoy](https://www.expedia.co.uk/Savoy-Hotels-Hilton-Hotels.0-0-d6005417--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Savoy Hotels](https://www.expedia.co.uk/Savoy-Hotels.d6005417.Travel-Guide-Hotels) - [Washington Hotels](https://www.expedia.co.uk/Washington-Hotels.d553248634998690770.Travel-Guide-Hotels) - [Hotels near Williams College Museum of Art](https://www.expedia.co.uk/Williams-College-Museum-Of-Art-Hotels.0-l6091837-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Williamstown](https://www.expedia.co.uk/Williamstown-Hotels-Gay-Friendly-Hotel.0-0-d7859-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Williamstown](https://www.expedia.co.uk/Williamstown-Hotels-Luxury-Hotel.0-0-d7859-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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[Flights to Williamstown](https://www.expedia.co.uk/Cheap-Flights-To-Williamstown.d7859.Travel-Guide-Flights) - [Flights from Peru](https://www.expedia.co.uk/lp/flights/553248634999167831/flights-from-peru) - [Flights from Hinsdale](https://www.expedia.co.uk/lp/flights/6005406/flights-from-hinsdale) - [Flights from Plainfield](https://www.expedia.co.uk/lp/flights/6005414/flights-from-plainfield) - [Flights from Windsor](https://www.expedia.co.uk/lp/flights/6005427/flights-from-windsor) - [Flights from Lenox](https://www.expedia.co.uk/lp/flights/8587/flights-from-lenox) - [Flights from North Adams](https://www.expedia.co.uk/lp/flights/9137/flights-from-north-adams) - [Flights from Pittsfield](https://www.expedia.co.uk/lp/flights/9478/flights-from-pittsfield) - [Flights from New York (JFK) to Pittsfield (PSF)](https://www.expedia.co.uk/lp/flights/jfk/psf/new-york-to-pittsfield) - [Visit Amherst](https://www.expedia.co.uk/Amherst.dx5948) - [Ashuwillticook Rail Trail Holidays](https://www.expedia.co.uk/Ashuwillticook-Rail-Trail.d811531152953708544.Holidays-City-Breaks) - [Visit Ashuwillticook Rail Trail](https://www.expedia.co.uk/Ashuwillticook-Rail-Trail.dx811531152953708544) - [Visit Becket](https://www.expedia.co.uk/Becket.dx6005395) - [Visit Berkshire County](https://www.expedia.co.uk/Berkshire-County.dx553248635083901436) - [Visit Blandford](https://www.expedia.co.uk/Blandford.dx80625) - [Visit Colrain](https://www.expedia.co.uk/Colrain.dx91560) - [Cummington Holidays](https://www.expedia.co.uk/Cummington.d183324.Holidays-City-Breaks) - [Visit Cummington](https://www.expedia.co.uk/Cummington.dx183324) - [Drury Holidays](https://www.expedia.co.uk/Drury.d3000748865.Holidays-City-Breaks) - [Visit East Longmeadow](https://www.expedia.co.uk/East-Longmeadow.dx6005400) - [Visit Goshen](https://www.expedia.co.uk/Goshen.dx109585) - [Visit Great Barrington](https://www.expedia.co.uk/Great-Barrington.dx110336) - [Visit Greenfield](https://www.expedia.co.uk/Greenfield.dx8027) - [Hancock Holidays](https://www.expedia.co.uk/Hancock.d112303.Holidays-City-Breaks) - [Visit Hancock](https://www.expedia.co.uk/Hancock.dx112303) - [Lanesborough Holidays](https://www.expedia.co.uk/Lanesborough.d6005408.Holidays-City-Breaks) - [Lenox Holidays](https://www.expedia.co.uk/Lenox.d8587.Holidays-City-Breaks) - [Visit Lenox](https://www.expedia.co.uk/Lenox.dx8587) - [Visit Longmeadow](https://www.expedia.co.uk/Longmeadow.dx6005409) - [Visit Mill River](https://www.expedia.co.uk/Mill-River.dx3000748895) - [New Ashford Holidays](https://www.expedia.co.uk/New-Ashford.d183333.Holidays-City-Breaks) - [North Adams Public Library](https://www.expedia.co.uk/North-Adams-Public-Library-North-Adams.d553248621532666701.Attraction) - [Visit North Adams](https://www.expedia.co.uk/North-Adams.dx9137) - [Visit Northampton](https://www.expedia.co.uk/Northampton.dx9187) - [Visit Orange](https://www.expedia.co.uk/Orange.dx6348110) - [Visit Pittsfield](https://www.expedia.co.uk/Pittsfield.dx9478) - [Visit Sandisfield](https://www.expedia.co.uk/Sandisfield.dx6005416) - [Savoy Holidays](https://www.expedia.co.uk/Savoy.d6005417.Holidays-City-Breaks) - [Visit Shelburne Falls](https://www.expedia.co.uk/Shelburne-Falls.dx6294302) - [Visit Southampton](https://www.expedia.co.uk/Southampton.dx6005419) - [Visit Springfield](https://www.expedia.co.uk/Springfield.dx6047669) - [Visit Stockbridge](https://www.expedia.co.uk/Stockbridge.dx162575) - [Visit Sunderland](https://www.expedia.co.uk/Sunderland.dx3000441543) - [Visit The Berkshires](https://www.expedia.co.uk/The-Berkshires.dx6047665) - [Visit Turners Falls](https://www.expedia.co.uk/Turners-Falls.dx6005422) - [Visit West Stockbridge](https://www.expedia.co.uk/West-Stockbridge.dx173346) - [Visit Western Massachusetts](https://www.expedia.co.uk/Western-Massachusetts.dx6234063) - [Williams College](https://www.expedia.co.uk/Williams-College-Williamstown.d6091833.Attraction) - [Visit Williamstown](https://www.expedia.co.uk/Williamstown.dx7859) - [Windsor Holidays](https://www.expedia.co.uk/Windsor.d6005427.Holidays-City-Breaks) - [Car hire Adams](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Adams.d6005393.Car-Hire-Guide) - [Car hire Lenox](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lenox.d8587.Car-Hire-Guide) - [Car hire near Pittsfield State Forest](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield-State-Forest.d6339854.Car-Hire-Guide) - [Car hire Pittsfield](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield.d9478.Car-Hire-Guide) - [Car hire Williamstown](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Williamstown.d7859.Car-Hire-Guide) - [Florida Holiday Rentals](https://www.expedia.co.uk/Florida-Holiday-Rentals.d553248634999031091.Travel-Guide-HolidayRentals) - [Peru Holiday Rentals](https://www.expedia.co.uk/Peru-Holiday-Rentals.d553248634999167831.Travel-Guide-HolidayRentals) - Cities near Cheshire - Places of interest - [Tanglewood Music Center](https://expedia.co.uk/Tanglewood-Music-Center-Lenox.d503292.Attraction) - [Williams College](https://expedia.co.uk/Williams-College-Williamstown.d6091833.Attraction) - [Green Mountain National Forest](https://expedia.co.uk/Green-Mountain-National-Forest-Vermont.d6115904.Attraction) - [Norman Rockwell Museum](https://expedia.co.uk/Norman-Rockwell-Museum-Stockbridge.d6091839.Attraction) - [Ventfort Hall Mansion and Gilded Age Museum](https://expedia.co.uk/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Attraction) ![](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. 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