Title: Cheap Flights from Winchester - Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights from Winchester - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000447144.Destination-Travel-Guides) ## Popular airlines from Winchester - ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada - ![WestJet](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WS.svg) WestJet - ![Flair Airlines](https://a.travel-assets.com/air/airlines/f8_sq.svg) Flair Airlines - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![Porter Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_PD.svg) Porter Airlines - ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheapest flights from Winchester These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Dec 6 - Fri, Dec 12 BOS Boston MCO Orlando CA $111 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MCO,departure:06/12/2025TANYT&leg2=from:MCO,to:BOS,departure:12/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:110.88&airProductToken=AQovCi0IzpYBEgQxNDgzGMGTASDMcCiHhP8CMNOF_wI4UEAAWAFqAlJQcgZQQTIxTlIKLgosCM6WARIDODkwGMxwIMGTASiwwf8CMOfC_wI4V0AAWAFqAlJQcgZXQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Nov 15 - Wed, Nov 19 BOS Boston ATL Atlanta CA $120 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ATL,departure:15/11/2025TANYT&leg2=from:ATL,to:BOS,departure:19/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:119.90&airProductToken=AQpcCiwIzpYBEgMxMjYYwZMBIOVaKKSR_QIw9ZL9AjhQQABYAWoCUlByBlBBMTROUgosCM6WARIEMjMyMhjlWiDgXCiMlf0CMICW_QI4UEABWAFqAlJQcgZQQTE0TlIKXAosCM6WARIEMjI1NBjgXCDlWijBw_0CMK_E_QI4UEAAWAFqAlJQcgZQQTE0TlIKLAjOlgESAzg1MBjlWiDBkwEok8X9AjDLxv0COFBAAVgBagJSUHIGUEExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Nov 15 - Wed, Nov 19 BOS Boston FLL Fort Lauderdale CA $121 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:FLL,departure:15/11/2025TANYT&leg2=from:FLL,to:BOS,departure:19/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:120.77&airProductToken=AQouCiwIzpYBEgMxMjYYwZMBIOVaKKSR_QIw9ZL9AjhHQABYAWoCUlByBkdBMTROUgouCiwIzpYBEgM4NTAY5VogwZMBKJPF_QIwy8b9AjhHQABYAWoCUlByBkdBMTROUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sun, Feb 1 - Sat, Feb 7 BOS Boston MIA Miami CA $137 Roundtrip found 22 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:01/02/2026TANYT&leg2=from:MIA,to:BOS,departure:07/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:136.64&airProductToken=AQovCi0IzpYBEgQzMDUxGMGTASCMAijQgYQDMKSDhAM4R0AAWAFqAlJQcgZHQTE0TlIKLgosCM6WARIDNzYxGIwCIMGTASjyxYQDML7HhAM4R0AAWAFqAlJQcgZHQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Mon, Feb 2 - Fri, Feb 6 PVD Providence RSW Fort Myers CA $148 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PVD,to:RSW,departure:02/02/2026TANYT&leg2=from:RSW,to:PVD,departure:06/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:147.10&airProductToken=AQowCi4IwmwSBDE4OTEYrx0g0bQBKPSJhAMwv4uEAzhMQABYAWoCRE5yCFBJNFFCRUwxCjAKLgjCbBIEMTg5MhjRtAEgrx0o3rqEAzCNvIQDOExAAFgBagJETnIIUEk0UUJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Nov 15 - Wed, Nov 19 PSM Portsmouth MCO Orlando CA $149 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSM,to:MCO,departure:15/11/2025TANYT&leg2=from:MCO,to:PSM,departure:19/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:148.12&airProductToken=AQosCioIzbABEgM4NDcYz2QgzHAojpT9AjDelf0COEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDODQ2GMxwIM9kKK-__QIw5sD9AjhCQABYAWoCTk9yBUJOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Jan 17 - Sat, Jan 24 PSM Portsmouth RSW Fort Myers CA $170 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSM,to:RSW,departure:17/01/2026TANYT&leg2=from:RSW,to:PSM,departure:24/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:169.04&airProductToken=AQotCisIzbABEgM3ODEYz2Qg0bQBKNTbggMwxN2CAzhBQABYAWoCTk9yBUFOTzAwCi0KKwjNsAESAzc4MBjRtAEgz2QozKiDAzCMqoMDOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sun, Nov 9 - Thu, Nov 13 ALB Albany MCO Orlando CA $173 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALB,to:MCO,departure:09/11/2025TANYT&leg2=from:MCO,to:ALB,departure:13/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:172.88&airProductToken=AQosCioIzbABEgM4NTUY4AogzHAokdH8AjCV0_wCOERAAFgBagJOT3IFRE5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Jan 24 - Sat, Jan 31 MHT Manchester MCO Orlando CA $177 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MHT,to:MCO,departure:24/01/2026TANYT&leg2=from:MCO,to:MHT,departure:31/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:176.66&airProductToken=AQotCisIzbABEgM4MTcY7JkBIMxwKPmqgwMwy6yDAzhBQABYAWoCTk9yBUFOTzAwCi0KKwjNsAESAzgxNhjMcCDsmQEo8feDAzCx-YMDOEJAAFgBagJOT3IFQk5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Dec 6 - Fri, Dec 12 BOS Boston RSW Fort Myers CA $177 Roundtrip found 10 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:RSW,departure:06/12/2025TANYT&leg2=from:RSW,to:BOS,departure:12/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:177.00&airProductToken=AQowCi4IwmwSAzE2NRjBkwEg0bQBKKyD_wIwhYX_AjhMQABYAWoCRE5yCFBJMlFVT0wxCjEKLwjCbBIEMjE2NhjRtAEgwZMBKInE_wIwx8X_AjhMQABYAWoCRE5yCFBJMlFVRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Mon, Nov 17 - Sat, Nov 22 BDL Hartford MCO Orlando CA $180 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MCO,departure:17/11/2025TANYT&leg2=from:MCO,to:BDL,departure:22/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:179.67&airProductToken=AQosCioIzbABEgM4NTkY4VggzHAoyK39AjDPr_0COEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDNTIzGMxwIOFYKN3i_QIwheT9AjhEQABYAWoCTk9yBUROTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Feb 27 - Mon, Mar 2 BOS Boston TPA Tampa CA $187 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:TPA,departure:27/02/2026TANYT&leg2=from:TPA,to:BOS,departure:02/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:186.84&airProductToken=AQovCi0IzpYBEgQzNzY4GMGTASDzAyjAqYYDMI2rhgM4R0AAWAFqAlJQcgZHQTE0TlIKLwotCM6WARIEMzc2NRjzAyDBkwEosMWGAzDcxoYDOEdAAFgBagJSUHIGR0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Dec 2 - Wed, Dec 10 ALB Albany FLL Fort Lauderdale CA $195 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALB,to:FLL,departure:02/12/2025TANYT&leg2=from:FLL,to:ALB,departure:10/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:194.40&airProductToken=AQohCh8IwmwSBDEwODcY4Aog5VoorNH-AjD00v4COExAAFgBCiEKHwjCbBIEMTA4OBjlWiDgCiinsP8CMNyx_wI4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Jan 10 - Sat, Jan 17 ALB Albany RSW Fort Myers CA $198 Roundtrip found 9 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALB,to:RSW,departure:10/01/2026TANYT&leg2=from:RSW,to:ALB,departure:17/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:197.56&airProductToken=AQotCisIzbABEgM3NzkY4Aog0bQBKLuJggMwjYuCAzhBQABYAWoCTk9yBUFOTzAwCi0KKwjNsAESAzc3OBjRtAEg4AoosNaCAzDz14IDOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Dec 3 - Mon, Dec 15 MHT Manchester FLL Fort Lauderdale CA $198 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MHT,to:FLL,departure:03/12/2025TANYT&leg2=from:FLL,to:MHT,departure:15/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:197.60&airProductToken=AQoiCiAIwmwSBDEzNDMY7JkBIOVaKPLf_gIwveH-AjhMQABYAQoiCiAIwmwSBDEzNDQY5Vog7JkBKL3o_wIw-On_AjhMQABYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, Feb 8 - Wed, Feb 25 BDL Hartford TPA Tampa CA $202 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BDL,to:TPA,departure:08/02/2026TANYT&leg2=from:TPA,to:BDL,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:201.20&airProductToken=AQogCh4IwmwSAzUzMxjhWCDzAyiszoQDMO3PhAM4TEAAWAEKQAoeCMJsEgMyMjYY8wMgqVEogZKGAzCok4YDOExAAFgBCh4IwmwSAzY3NRipUSDhWCijlIYDMOWUhgM4TEABWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Mon, Dec 15 - Wed, Dec 24 BDL Hartford FLL Fort Lauderdale CA $202 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BDL,to:FLL,departure:15/12/2025TANYT&leg2=from:FLL,to:BDL,departure:24/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:201.70&airProductToken=AQovCi0IwmwSBDEyNTkY4Vgg5Voo0ej_AjCR6v8COExAAFgBagJETnIIUEkyUVVFTDEKLgosCMJsEgM0NjAY5Vog4Vgo886AAzCo0IADOExAAFgBagJETnIIUEkyUVVFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Fri, Jan 23 - Wed, Feb 4 PVD Providence MCO Orlando CA $207 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PVD,to:MCO,departure:23/01/2026TANYT&leg2=from:MCO,to:PVD,departure:04/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:206.07&airProductToken=AQpaCisIzbABEgM3NTQYrx0g8aABKOuegwMw5p-DAzhBQABYAWoCTk9yBUFOTzAwCisIzbABEgM4NTUY8aABIMxwKKmggwMwmaGDAzhBQAFYAWoCTk9yBUFOTzAwCiwKKgjNsAESAzcxNxjMcCCvHSifo4QDMM2khAM4QkAAWAFqAk5PcgVCTk8wMBIKCAEQARgBKgJNWBgBIgQIARABKAIoAygEMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, Nov 9 - Fri, Nov 14 BDL Hartford MIA Miami CA $249 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MIA,departure:09/11/2025TANYT&leg2=from:MIA,to:BDL,departure:14/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.10&airProductToken=AQozCjEIwYIBEgQxMjQwGOFYIIwCKL3N_AIwh8_8AjhCQABYAWoFQkFTSUNyCE83REpaU0JYCjMKMQjBggESBDEyNTYYjAIg4Vgo7Yz9AjCojv0COEJAAFgBagVCQVNJQ3IIT1VESlpTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 5 - Tue, Jan 13 ALB Albany MIA Miami CA $304 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALB,to:MIA,departure:05/01/2026TANYT&leg2=from:MIA,to:ALB,departure:13/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:303.30&airProductToken=AQpECiAIxJgBEgQ1MjY4GOAKIMsBKP7SgQMww9OBAzhFQABYAQogCMSYARIEMTM3NxjLASCMAiiw1IEDMILWgQM4RUABWAEKRAogCMSYARIEMTI2MRiMAiDgXCj7qYIDMPeqggM4RUAAWAEKIAjEmAESBDExMzcY4Fwg4AooqquCAzCyrIIDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ## Flights from Winchester: Essential Travel Information | Cheapest flight from Winchester | CA $111 (roundtrip) | | --- | --- | | Best airlines to fly from Winchester | Spirit Airlines, JetBlue Airways, Breeze Airways, American Airlines, Delta | | Cheapest month to fly from Winchester | December | | Winchester IATA code | EEN | | Winchester Country/State | New Hampshire | | Airline ticket deals from Winchester | CA $111 - CA $304 | ## How to find cheap flights from Winchester #### How much is a flight from Winchester? Flights from Winchester are available at a range of prices. Attractive deals include one-way fares and roundtrip fares from CA $111. You'll often find the best deals in December. With Expedia, explore offers from multiple airlines and plan your journey effortlessly, ensuring you secure the perfect flight at a competitive price. #### How can I find cheap flights from Winchester? Discovering affordable flights from Winchester has never been easier, thanks to Expedia. We present a simple solution for comparing fares to a multitude of destinations, with one-way deals and roundtrip offers from CA $111. After choosing an enticing deal, enhance your search with our filters and sort by 'Price (Lowest)' to find the most economical and suitable options. Begin your journey with us today and relish the simplicity of securing cost-effective flights. #### How can I get the best deal on flights from Winchester? For the best deal on flights from Winchester, flexibility is key. Utilize our 'Show flexible dates' feature on Expedia to compare prices for different dates, and you may find deals when such offers are present. Remember, direct flights from Winchester could come with a higher price tag, and different airlines' baggage policies might affect the total cost. Stay tuned with our latest offers to make the most of your travel budget. #### What is the best airline to fly with from Winchester? With Expedia, finding the best airline for your journey from Winchester is a breeze. We offer options from 20 different airlines, including Spirit Airlines, JetBlue Airways, Breeze Airways, American Airlines, Delta. Whether you prioritize price, comfort, or loyalty programs, we have a fit for your travel needs. #### What is the best month to fly from Winchester? The best month to fly from Winchester is typically December, as it often offers great deals. If you're looking to save on your journey, start your search with Expedia. We provide options to filter for the lowest possible prices, including those from one-way and roundtrip from CA $111 fares. However, remember that airfare can fluctuate based on the time of year and ticket availability. #### When is the best time to book/buy flights from Winchester? Secure the best savings with Expedia. Data suggests that booking flights from Winchester three weeks in advance can save you up to 20%. Also, consider flying in December for the best rates. Stay updated with us for the latest data and savings advice. #### Are there any last-minute flights from Winchester? With Expedia, finding last-minute flights from Winchester has never been easier. We offer you a chance to explore the best deals from 20 airlines. Even if you're planning to travel immediately, you can access a variety of options, including one-way and roundtrip from CA $111 fares. Start exploring now and seize the top offers available over the next two weeks. Rest assured, you can find a perfect flight even at the last minute. #### Why book with Expedia? Choose Expedia for unbeatable prices, exceptional value, and substantial savings. We offer a wide selection of routes from Winchester, with flight options from 20 airlines, including one-way deals . Customize your journey to suit your needs and achieve even more savings by bundling your flight with a hotel or car hire. Start planning your trip with us today and earn rewards points with every booking. #### Can I change/cancel my flight? Absolutely, at Expedia, you can change or cancel your flight. However, fees and refund policies depend on your flight agreement, as each airline has distinct rules for exchanges and refunds. For detailed information, check your itinerary or visit our customer service portal. To maximize flexibility, opt for flights with no change fees using our 'Flexible change policies' filter. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars ### Lodging - [4 Star Hotels in Keene](https://www.expedia.ca/4Star-Keene-Hotels.s40-0-d6057413.Travel-Guide-Filter-Hotels) - [Hotels near Asbury United Methodist Church](https://www.expedia.ca/Asbury-United-Methodist-Church-Hotels.0-l6265749-0.Travel-Guide-Filter-Hotels) - [Castles in Cheshire County](https://www.expedia.ca/Cheshire-County-Castles.d553248635976430851-aaCastles.Travel-Guide-Accommodation) - [B&B in Chesterfield](https://www.expedia.ca/Chesterfield-Bed-And-Breakfast.d6052872-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chesterfield Hotels](https://www.expedia.ca/Chesterfield-Hotels.d6052872.Travel-Guide-Hotels) - [Inns in Chesterfield](https://www.expedia.ca/Chesterfield-Inns.d6052872-aaInns.Travel-Guide-Accommodation) - [Resorts in Chesterfield](https://www.expedia.ca/Chesterfield-Resort-Hotels.d6052872-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Colonial Theatre](https://www.expedia.ca/Colonial-Theatre-Hotels.0-l553248621532666941-0.Travel-Guide-Filter-Hotels) - [Guest Houses in East Swanzey](https://www.expedia.ca/East-Swanzey-Guest-Houses.d553248635976384897-aaGuestHouses.Travel-Guide-Accommodation) - [Farmstay in Fitzwilliam](https://www.expedia.ca/Fitzwilliam-Agritourism.d104340-aaAgritourism.Travel-Guide-Accommodation) - [Fitzwilliam Hotels](https://www.expedia.ca/Fitzwilliam-Hotels.d104340.Travel-Guide-Hotels) - [Lodges in Fitzwilliam](https://www.expedia.ca/Fitzwilliam-Lodges.d104340-aaLodges.Travel-Guide-Accommodation) - [Luxury Hotels in Hinsdale](https://www.expedia.ca/Hinsdale-Hotels-Luxury-Hotel.0-0-d3000447021-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hinsdale Hotels](https://www.expedia.ca/Hinsdale-Hotels.d3000447021.Travel-Guide-Hotels) - [Hotels near Historic Main Street](https://www.expedia.ca/Historic-Main-Street-Hotels.0-l6337582-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Keene](https://www.expedia.ca/Keene-Apart-Hotels.d6057413-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Keene](https://www.expedia.ca/Keene-Bed-And-Breakfast.d6057413-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Keene](https://www.expedia.ca/Keene-Cabins.d6057413-aaCabins.Travel-Guide-Accommodation) - [Chalets in Keene](https://www.expedia.ca/Keene-Chalets.d6057413-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Keene](https://www.expedia.ca/Keene-Guest-Houses.d6057413-aaGuestHouses.Travel-Guide-Accommodation) - [Hostels in Keene](https://www.expedia.ca/Keene-Hostels.d6057413-aaHostels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Keene](https://www.expedia.ca/Keene-Hotels-Adults-Only-Resorts.0-0-d6057413-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Keene](https://www.expedia.ca/Keene-Hotels-Beach-Hotel.0-0-d6057413-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Keene](https://www.expedia.ca/Keene-Hotels-Cheap-Hotels.0-0-d6057413-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Keene](https://www.expedia.ca/Keene-Hotels-Hotel-With-Early-Check-In.0-0-d6057413-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Keene](https://www.expedia.ca/Keene-Hotels-Hotel-With-Pool.0-0-d6057413-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Keene](https://www.expedia.ca/Keene-Hotels-Hotels-With-Free-Parking.0-0-d6057413-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Keene](https://www.expedia.ca/Keene-Hotels-Hotels-With-Kitchenettes.0-0-d6057413-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Keene](https://www.expedia.ca/Keene-Hotels-Luxury-Hotel.0-0-d6057413-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Keene](https://www.expedia.ca/Keene-Hotels-Spa-Hotel.0-0-d6057413-tSpaHotel.Travel-Guide-Filter-Hotels) - [Keene Hotels](https://www.expedia.ca/Keene-Hotels.d6057413.Travel-Guide-Hotels) - [Inns in Keene](https://www.expedia.ca/Keene-Inns.d6057413-aaInns.Travel-Guide-Accommodation) - [Motels in Keene](https://www.expedia.ca/Keene-Motels.d6057413-aaMotels.Travel-Guide-Accommodation) - [Resorts in Keene](https://www.expedia.ca/Keene-Resort-Hotels.d6057413-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Keene State College](https://www.expedia.ca/Keene-State-College-Hotels.0-l553248621533117511-0.Travel-Guide-Filter-Hotels) - [Villas in Keene](https://www.expedia.ca/Keene-Villas.d6057413-aaVillas.Travel-Guide-Accommodation) - [Hotels near Laurel Lake](https://www.expedia.ca/Laurel-Lake-Hotels.0-l553248635976195216-0.Travel-Guide-Filter-Hotels) - [Richmond Hotels](https://www.expedia.ca/Richmond-Hotels.d553248634999245866.Travel-Guide-Hotels) - [Chalets in Spofford](https://www.expedia.ca/Spofford-Chalets.d6267420-aaChalets.Travel-Guide-Accommodation) - [Spofford Hotels](https://www.expedia.ca/Spofford-Hotels.d6267420.Travel-Guide-Hotels) - [Hotels near Stonewall Farm](https://www.expedia.ca/Stonewall-Farm-Hotels.0-l553248621532666932-0.Travel-Guide-Filter-Hotels) - [Castles in Swanzey](https://www.expedia.ca/Swanzey-Castles.d6348108-aaCastles.Travel-Guide-Accommodation) - [Cheap Hotels in Swanzey](https://www.expedia.ca/Swanzey-Hotels-Cheap-Hotels.0-0-d6348108-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Swanzey](https://www.expedia.ca/Swanzey-Hotels-Luxury-Hotel.0-0-d6348108-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Swanzey Hotels](https://www.expedia.ca/Swanzey-Hotels.d6348108.Travel-Guide-Hotels) - [Motels in Swanzey](https://www.expedia.ca/Swanzey-Motels.d6348108-aaMotels.Travel-Guide-Accommodation) - [B&B in Troy](https://www.expedia.ca/Troy-Bed-And-Breakfast.d183587-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Troy](https://www.expedia.ca/Troy-Chalets.d183587-aaChalets.Travel-Guide-Accommodation) - [Cheap Hotels in Troy](https://www.expedia.ca/Troy-Hotels-Cheap-Hotels.0-0-d183587-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Troy](https://www.expedia.ca/Troy-Hotels-Hotel-With-Pool.0-0-d183587-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Troy Hotels](https://www.expedia.ca/Troy-Hotels.d183587.Travel-Guide-Hotels) - [Lodges in Troy](https://www.expedia.ca/Troy-Lodges.d183587-aaLodges.Travel-Guide-Accommodation) - [Rv Parks in Troy](https://www.expedia.ca/Troy-RV-Parks.d183587-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Troy](https://www.expedia.ca/Troy-Resort-Hotels.d183587-aaResortHotels.Travel-Guide-Accommodation) - [B&B in West Chesterfield](https://www.expedia.ca/West-Chesterfield-Bed-And-Breakfast.d183592-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Spa Hotels in West Chesterfield](https://www.expedia.ca/West-Chesterfield-Hotels-Spa-Hotel.0-0-d183592-tSpaHotel.Travel-Guide-Filter-Hotels) - [West Chesterfield Hotels](https://www.expedia.ca/West-Chesterfield-Hotels.d183592.Travel-Guide-Hotels) - [Inns in West Chesterfield](https://www.expedia.ca/West-Chesterfield-Inns.d183592-aaInns.Travel-Guide-Accommodation) - [Resorts in West Chesterfield](https://www.expedia.ca/West-Chesterfield-Resort-Hotels.d183592-aaResortHotels.Travel-Guide-Accommodation) ### Flights - [Flights to Keene](https://www.expedia.ca/Cheap-Flights-To-Keene.d6057413.Travel-Guide-Flights) - [Flights to Spofford](https://www.expedia.ca/Cheap-Flights-To-Spofford.d6267420.Travel-Guide-Flights) - [Flights from Lebanon](https://www.expedia.ca/lp/flights/2041/flights-from-lebanon) - [Flights from New Hampshire](https://www.expedia.ca/lp/flights/231/flights-from-new-hampshire) - [Flights from Acworth](https://www.expedia.ca/lp/flights/3000421385/flights-from-acworth) - [Flights from Alstead](https://www.expedia.ca/lp/flights/3000421387/flights-from-alstead) - [Flights from Canaan](https://www.expedia.ca/lp/flights/3000446830/flights-from-canaan) - [Flights from Canterbury](https://www.expedia.ca/lp/flights/3000446832/flights-from-canterbury) - [Flights from Hollis](https://www.expedia.ca/lp/flights/3000447020/flights-from-hollis) - [Flights from Marlborough](https://www.expedia.ca/lp/flights/3000447046/flights-from-marlborough) - [Flights from Mason](https://www.expedia.ca/lp/flights/3000447047/flights-from-mason) - [Flights from Raymond](https://www.expedia.ca/lp/flights/3000447089/flights-from-raymond) - [Flights from Stoddard](https://www.expedia.ca/lp/flights/3000447111/flights-from-stoddard) - [Flights from Westmoreland](https://www.expedia.ca/lp/flights/3000447140/flights-from-westmoreland) - [Flights from Brookline](https://www.expedia.ca/lp/flights/553248634998736702/flights-from-brookline) - [Flights from Nelson](https://www.expedia.ca/lp/flights/553248634999089107/flights-from-nelson) - [Flights from Lempster](https://www.expedia.ca/lp/flights/553248634999089825/flights-from-lempster) - [Flights from Hill](https://www.expedia.ca/lp/flights/553248634999212469/flights-from-hill) - [Flights from Dartmouth-Lake Sunapee Region](https://www.expedia.ca/lp/flights/553248635975748853/flights-from-dartmouth-lake-sunapee-region) - [Flights from Etna](https://www.expedia.ca/lp/flights/553248635975876283/flights-from-etna) - [Flights from Peterborough](https://www.expedia.ca/lp/flights/55898/flights-from-peterborough) - [Flights from Manchester](https://www.expedia.ca/lp/flights/6025582/flights-from-manchester) - [Flights from Danbury](https://www.expedia.ca/lp/flights/6052729/flights-from-danbury) - [Flights from Southern New Hampshire](https://www.expedia.ca/lp/flights/6057417/flights-from-southern-new-hampshire) - [Flights from Hooksett](https://www.expedia.ca/lp/flights/6084353/flights-from-hooksett) - [Flights from Nashua](https://www.expedia.ca/lp/flights/6167/flights-from-nashua) - [Flights from Grafton](https://www.expedia.ca/lp/flights/6348406/flights-from-grafton) - [Flights from Wilmot](https://www.expedia.ca/lp/flights/6350217/flights-from-wilmot) - [Flights from Salem](https://www.expedia.ca/lp/flights/6603/flights-from-salem) - [Flights from Concord](https://www.expedia.ca/lp/flights/6656/flights-from-concord) - [Flights from Claremont](https://www.expedia.ca/lp/flights/89784/flights-from-claremont) - [Flights from Dublin](https://www.expedia.ca/lp/flights/98112/flights-from-dublin) - [Flights from Boston (BOS) to Keene (EEN)](https://www.expedia.ca/lp/flights/bos/een/boston-to-keene) - [Flights from Las Vegas (LAS) to Keene (EEN)](https://www.expedia.ca/lp/flights/las/een/las-vegas-to-keene) - [Flights from West Palm Beach (PBI) to Keene (EEN)](https://www.expedia.ca/lp/flights/pbi/een/west-palm-beach-to-keene) - [Flights from Tampa (TPA) to Keene (EEN)](https://www.expedia.ca/lp/flights/tpa/een/tampa-to-keene) ### Packages - [Visit Cheshire County](https://www.expedia.ca/Cheshire-County.dx553248635976430851) - [Visit Keene](https://www.expedia.ca/Keene.dx6057413) - [Visit West Chesterfield](https://www.expedia.ca/West-Chesterfield.dx183592) ### Cars - [Alamo Rent A Car Rental Cars in Keene](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Keene.d6057413-c6.Car-Rental-Guide-Suppliers) - [Car rental Keene](https://www.expedia.ca/Car-Rentals-In-Keene.d6057413.Car-Rental-Guide) \*Available to Expedia members.