Title: Cheap flights from Winchester, NH - Expedia.com ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap flights from Winchester, NH - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers 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 [Winchester Travel Guide](https://expedia.com/Winchester.dx3000447144)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d3000447144.Destination-Travel-Guides) ## Popular airlines from Winchester - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines - ![](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\* - ![](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\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheapest flights from Winchester These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sun, Mar 1 - Thu, Mar 5 BDL Hartford MCO Orlando $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MCO,departure:3/1/2026TANYT&leg2=from:MCO,to:BDL,departure:3/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDE2ODMY4VggzHAo4sCGAzCYwoYDOEVAAFgBagRQQ18xcgdLMjFEWFMyCjAKLgjGchIEMTY4NBjMcCDhWCi454YDMOnohgM4RUAAWAFqBFBDXzFyB0syMURYUzISDAgBEAEYASoCRjkyABgBIgQIARABKAIoAzAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 3 - Tue, Mar 10 BOS Boston FLL Fort Lauderdale $68 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:FLL,departure:3/3/2026TANYT&leg2=from:FLL,to:BOS,departure:3/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:67.38&airProductToken=AQoxCi8IzpYBEgQyMjMxGMGTASDlWiju1YYDMMvXhgM4V0AAWAFqAlJQcghXMjFTWUJWMgowCi4IzpYBEgM3NDMY5VogwZMBKKClhwMw4KaHAzhXQABYAWoCUlByCFcyMVNZQlYyEgwIARABGAEqAk5LMgAYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 3 - Wed, Mar 4 BOS Boston MIA Miami $70 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:3/3/2026TANYT&leg2=from:MIA,to:BOS,departure:3/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:69.38&airProductToken=AQoxCi8IzpYBEgQzMDMzGMGTASCMAija1YYDMLjXhgM4V0AAWAFqAlJQcghXMjFTWUJWMgovCi0IzpYBEgQzMDMyGIwCIMGTASjt3oYDMLnghgM4V0AAWAFqAlJQcgZXQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 3 - Wed, Mar 4 BOS Boston MCO Orlando $74 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MCO,departure:3/3/2026TANYT&leg2=from:MCO,to:BOS,departure:3/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:73.38&airProductToken=AQovCi0IzpYBEgQyODgyGMGTASDMcCin04YDMPbUhgM4V0AAWAFqAlJQcgZXVFJHQzYKLwotCM6WARIEMTYxNBjMcCDBkwEowOGGAzD14oYDOFdAAFgBagJSUHIGV0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sun, Apr 5 - Thu, Apr 9 BDL Hartford MIA Miami $77 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MIA,departure:4/5/2026TANYT&leg2=from:MIA,to:BDL,departure:4/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:76.96&airProductToken=AQowCi4IxnISBDI2NTMY4VggjAIoxMmJAzCEy4kDOEVAAFgBagRQQ18xcgdaMDdEWFM5CjAKLgjGchIEMjY1NBiMAiDhWCjN9IkDMI32iQM4RUAAWAFqBFBDXzFyB0syMVJYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sun, Feb 22 - Sun, Mar 1 BDL Hartford ATL Atlanta $80 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:ATL,departure:2/22/2026TANYT&leg2=from:ATL,to:BDL,departure:3/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:79.96&airProductToken=AQowCi4IxnISBDEzMDUY4Vgg4Fwo7-6FAzCc8IUDOEVAAFgBagRQQ18xcgdaMDdZWFM5CjAKLgjGchIEMTMwNhjgXCDhWCiIvIYDMJi9hgM4RUAAWAFqBFBDXzFyB1owN1lYUzkSDAgBEAEYASoCRjkyABgBIgQIARABKAIoAzAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Mar 4 - Wed, Mar 11 BOS Boston RSW Fort Myers $94 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:RSW,departure:3/4/2026TANYT&leg2=from:RSW,to:BOS,departure:3/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:93.38&airProductToken=AQowCi4IzpYBEgQzMjcxGMGTASDRtAEotNuGAzCR3YYDOEdAAFgBagJSUHIGR1RSR0QxCi8KLQjOlgESAzI2OBjRtAEgwZMBKParhwMws62HAzhHQABYAWoCUlByBkdUUkdEMRIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, May 30 - Sat, Jun 6 PSM Portsmouth MCO Orlando $94 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PSM,to:MCO,departure:5/30/2026TANYT&leg2=from:MCO,to:PSM,departure:6/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:93.50&airProductToken=AQosCioIzbABEgM4NDcYz2QgzHAonLOOAzDqtI4DOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDODQ2GMxwIM9kKJqAjwMw1IGPAzhBQABYAWoCTk9yBUFOTzAwEgwIARABGAEqAk1YMgAYASIECAEQASgCKAMoBDAN) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Aug 22 - Sat, Aug 29 ALB Albany RSW Fort Myers $102 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ALB,to:RSW,departure:8/22/2026TANYT&leg2=from:RSW,to:ALB,departure:8/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:101.22&airProductToken=AQotCisIzbABEgM3NzkY4Aog0bQBKK7klQMwgOaVAzhBQABYAWoCTk9yBUFOTzAwCi0KKwjNsAESAzc3OBjRtAEg4Aooo7GWAzDmspYDOEFAAFgBagJOT3IFQU5PMDASDAgBEAEYASoCTVgyABgBIgQIARABKAIoAygEMA0) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Fri, Sep 11 - Mon, Sep 14 PVD Providence TPA Tampa $107 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PVD,to:TPA,departure:9/11/2026TANYT&leg2=from:TPA,to:PVD,departure:9/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:106.22&airProductToken=AQosCioIzbABEgM3MTgYrx0g8wMo3b-XAzCiwZcDOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDNzE5GPMDIK8dKKrjlwMw4uSXAzhCQABYAWoCTk9yBUJOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Feb 28 - Wed, Mar 4 PVD Providence FLL Fort Lauderdale $110 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PVD,to:FLL,departure:2/28/2026TANYT&leg2=from:FLL,to:PVD,departure:3/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:109.22&airProductToken=AQosCioIzbABEgM3MzAYrx0g5VoogrKGAzCitIYDOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDNzMxGOVaIK8dKJLfhgMwmOGGAzhDQABYAWoCTk9yBUNOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Feb 24 - Thu, Feb 26 BOS Boston SJU San Juan $111 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:SJU,departure:2/24/2026TANYT&leg2=from:SJU,to:BOS,departure:2/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:110.99&airProductToken=AQovCi0IzpYBEgQzOTA4GMGTASCyogEo_YeGAzD0iYYDOFdAAFgBagJSUHIFV0E3TlIKLwotCM6WARIEMzkwNxiyogEgwZMBKPKbhgMw_J2GAzhXQABYAWoCUlByBVdBN05SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Sep 5 - Sat, Sep 12 MHT Manchester RSW Fort Myers $112 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MHT,to:RSW,departure:9/5/2026TANYT&leg2=from:RSW,to:MHT,departure:9/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:111.22&airProductToken=AQouCiwIzbABEgM3ODMY7JkBING0ASj__ZYDMNb_lgM4QUAAWAFqAk5PcgVBTk8wMAouCiwIzbABEgM3ODIY0bQBIOyZASj4ypcDMLfMlwM4QUAAWAFqAk5PcgVBTk8wMBIKCAEQARgBKgJNWBgBIgQIARABKAIoAygEMA0) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Mon, Aug 24 - Wed, Aug 26 PVD Providence RSW Fort Myers $112 Roundtrip found 5 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PVD,to:RSW,departure:8/24/2026TANYT&leg2=from:RSW,to:PVD,departure:8/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:111.22&airProductToken=AQotCisIzbABEgM3MTIYrx0g0bQBKJj1lQMw4_aVAzhCQABYAWoCTk9yBUJOTzAwCi0KKwjNsAESAzcxMxjRtAEgrx0ow46WAzD_j5YDOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Wed, Aug 26 - Tue, Sep 1 PVD Providence MCO Orlando $112 Roundtrip found 13 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PVD,to:MCO,departure:8/26/2026TANYT&leg2=from:MCO,to:PVD,departure:9/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:111.22&airProductToken=AQosCioIzbABEgM3MTYYrx0gzHAo3YuWAzCWjZYDOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDNzE3GMxwIK8dKIXSlgMwttOWAzhCQABYAWoCTk9yBUJOTzAwEgwIARABGAEqAk1YMgAYASIECAEQASgCKAMoBDAN) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Mon, Aug 24 - Wed, Aug 26 BDL Hartford TPA Tampa $122 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:TPA,departure:8/24/2026TANYT&leg2=from:TPA,to:BDL,departure:8/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:121.22&airProductToken=AQosCioIzbABEgM1MzIY4Vgg8wMo7fWVAzCp95UDOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDNTMzGPMDIOFYKJ6PlgMwzpCWAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Mar 28 - Tue, Mar 31 ORH Worcester RSW Fort Myers $123 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORH,to:RSW,departure:3/28/2026TANYT&leg2=from:RSW,to:ORH,departure:3/31/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:122.49&airProductToken=AQoiCiAIwmwSBDI4MzMYrjwg0bQBKPbsiAMwue6IAzhMQABYAQoiCiAIwmwSBDI4MzQY0bQBIK48KMOMiQMw-o2JAzhMQABYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Mar 31 - Sat, Apr 4 ORH Worcester MCO Orlando $123 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORH,to:MCO,departure:3/31/2026TANYT&leg2=from:MCO,to:ORH,departure:4/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:122.49&airProductToken=AQouCiwIwmwSAzk4NxiuPCDMcCixjYkDMOmOiQM4TEAAWAFqAkROcghQSTJRVUVMMQouCiwIwmwSAzQ4OBjMcCCuPCjLuIkDMPq5iQM4TEAAWAFqAkROcghQSTJRVUVMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sun, Apr 26 - Thu, Apr 30 ALB Albany MCO Orlando $130 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ALB,to:MCO,departure:4/26/2026TANYT&leg2=from:MCO,to:ALB,departure:4/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:129.01&airProductToken=AQovCi0I15wBEgMxNzgY4AogzHAotrSLAzDqtYsDOFZAAFgBagNXR0FyB1ZMTlZIMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Apr 11 - Sat, Apr 18 PSM Portsmouth RSW Fort Myers $137 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PSM,to:RSW,departure:4/11/2026TANYT&leg2=from:RSW,to:PSM,departure:4/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:136.28&airProductToken=AQotCisIzbABEgM3ODEYz2Qg0bQBKJiMigMwiI6KAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ## Flights from Winchester: Essential Travel Information | Cheapest flight from Winchester | $56 (roundtrip) | | ------------------------------------- | --------------------------------------------------------------------------------------- | | Best airlines to fly from Winchester | Frontier Airlines, Spirit Airlines, Breeze Airways, JetBlue Airways, Southwest Airlines | | Cheapest month to fly from Winchester | March | | Winchester IATA code | EEN | | Winchester Country/State | New Hampshire | | Airline ticket deals from Winchester | $56 - $137 | ## How to Find Cheap Flights from Winchester, NH #### How much is a flight from Winchester? This week, flights from Winchester are available between $56 – $137\. #### How to find cheap flights from Winchester? Expedia makes it easy to compare cheap flights from Winchester to many destinations. Check out excellent deals on domestic and international flights from Winchester. Once you select an offer, use our filters and sort by “Price (Lowest)” to see some of the cheapest and suitable options. #### How can I get the best deal on flights from Winchester? On Expedia, you have some of best airline ticket deals at your fingertips. Whether it’s a beach escape with your partner, a family vacation with your kids, or business trip with colleagues, these low airline ticket prices mean more savings for you. An excellent strategy for finding some of the best deals on flights from Winchester is to be flexible with your dates. Within each offer, you can compare prices for similar timeframes using our “Show flexible dates” feature. Depending on your destination, direct flights from Winchester may be more expensive. Airlines with strict bag policies or fees can also impact your costs. #### What is the best airline to fly from Winchester? At Expedia, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Winchester with: Frontier Airlines, Spirit Airlines, Breeze Airways, JetBlue Airways, Southwest Airlines. #### What is the best month to fly from Winchester? One of the cheapest times to fly from Winchester airport(s) is March, based on the current list of flights available now. Prices on plane tickets vary considerably throughout the year due to availability and seasonal demand. #### Are there any last-minute flights from Winchester? Expedia is the place to find last-minute flights from Winchester, making it easy for you to compare prices on flights in the near future for different combinations of travel dates and from multiple airlines. We source some of the best deals for you and display some of the best offers available over the next 2 weeks. #### Why book your ticket with Expedia? Booking flights from Winchester with Expedia is the obvious choice to get low prices, save money, and see more value from every dollar spent. We show you some of the best deals happening right now and provide a vast inventory of airlines and flight routes to choose from, so you can find some of the cheapest flights from Winchester. You can customize your journey to your timeline, route preferences, budget, rewards programs, and more. #### Can I change/cancel my flight? Some flights can be changed or canceled, but fees and refunds will depend on the unique terms of your flight agreement. Airlines have different rules and restrictions for exchanging or refunding flights. For more information, go to your itinerary or visit our [customer service portal](https://www.expedia.com/service/). We recommend choosing flights with no change fees for the most flexibility. Filter by “Flexible change policies” to see flights with no change fees. \*Data specialists from both ARC and Expedia Group analysed ARC's global flight data to distil actionable information to help people save money on travel. While it's impossible to guarantee when to find the lowest prices, after examining the variables, we were able to observe trends. Analysis based on ARC, round-trip flight data between 1 October 2017 - 30 September 2018 for Economy and Premium cabin ATPs on a global basis. \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals ### Lodging - [Ashuelot Hotels ](https://www.expedia.com/Ashuelot-Hotels.d3000421398.Travel-Guide-Hotels) - [Vacation Homes in Ashuelot ](https://www.expedia.com/Ashuelot-Private-Vacation-Homes.d3000421398-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Hinsdale Hotels ](https://www.expedia.com/Hinsdale-Hotels.d3000447021.Travel-Guide-Hotels) - [Cottages in Hinsdale ](https://www.expedia.com/Hinsdale-Cottages.d3000447021-aaCottages.Travel-Guide-Accommodation) - [4 Star Hotels in Hinsdale ](https://www.expedia.com/4Star-Hinsdale-Hotels.s40-0-d3000447021.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Hinsdale ](https://www.expedia.com/5Star-Hinsdale-Hotels.s50-0-d3000447021.Travel-Guide-Filter-Hotels) - [B&B in Hinsdale ](https://www.expedia.com/Hinsdale-Bed-And-Breakfast.d3000447021-aaBedAndBreakfast.Travel-Guide-Accommodation) - [3 Star Hotels in Hinsdale ](https://www.expedia.com/3Star-Hinsdale-Hotels.s30-0-d3000447021.Travel-Guide-Filter-Hotels) - [Motels in Hinsdale ](https://www.expedia.com/Hinsdale-Motels.d3000447021-aaMotels.Travel-Guide-Accommodation) - [Richmond Hotels ](https://www.expedia.com/Richmond-Hotels.d553248634999245866.Travel-Guide-Hotels) - [Cottages in Spofford ](https://www.expedia.com/Spofford-Cottages.d6267420-aaCottages.Travel-Guide-Accommodation) - [Spofford Hotels ](https://www.expedia.com/Spofford-Hotels.d6267420.Travel-Guide-Hotels) - [B&B in Spofford ](https://www.expedia.com/Spofford-Bed-And-Breakfast.d6267420-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Spofford ](https://www.expedia.com/Spofford-Motels.d6267420-aaMotels.Travel-Guide-Accommodation) - [3 Star Hotels in Spofford ](https://www.expedia.com/3Star-Spofford-Hotels.s30-0-d6267420.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Spofford ](https://www.expedia.com/Spofford-Cabins.d6267420-aaCabins.Travel-Guide-Accommodation) - [Apartments in Spofford ](https://www.expedia.com/Spofford-Apartments.d6267420-aaApartments.Travel-Guide-Accommodation) - [Lodges in Spofford ](https://www.expedia.com/Spofford-Lodges.d6267420-aaLodges.Travel-Guide-Accommodation) - [Vacation Homes in Spofford ](https://www.expedia.com/Spofford-Private-Vacation-Homes.d6267420-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Swanzey Hotels ](https://www.expedia.com/Swanzey-Hotels.d6348108.Travel-Guide-Hotels) - [Vacation Homes in Swanzey ](https://www.expedia.com/Swanzey-Private-Vacation-Homes.d6348108-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [B&B in Swanzey ](https://www.expedia.com/Swanzey-Bed-And-Breakfast.d6348108-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Swanzey ](https://www.expedia.com/Swanzey-Motels.d6348108-aaMotels.Travel-Guide-Accommodation) - [Cabin Rentals in Swanzey ](https://www.expedia.com/Swanzey-Cabins.d6348108-aaCabins.Travel-Guide-Accommodation) - [Pet-friendly Hotels in Swanzey ](https://www.expedia.com/Swanzey-Hotels-Pet-Friendly-Hotel.0-0-d6348108-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Swanzey ](https://www.expedia.com/4Star-Swanzey-Hotels.s40-0-d6348108.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Swanzey ](https://www.expedia.com/Swanzey-Hotels-Romantic-Hotel.0-0-d6348108-tRomanticHotel.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Swanzey ](https://www.expedia.com/3Star-Swanzey-Hotels.s30-0-d6348108.Travel-Guide-Filter-Hotels) - [Cottages in Swanzey ](https://www.expedia.com/Swanzey-Cottages.d6348108-aaCottages.Travel-Guide-Accommodation) - [Chesterfield Hotels ](https://www.expedia.com/Chesterfield-Hotels.d6052872.Travel-Guide-Hotels) - [Hotels near Asbury United Methodist Church ](https://www.expedia.com/Asbury-United-Methodist-Church-Hotels.0-l6265749-0.Travel-Guide-Filter-Hotels) - [Hotels near Madame Sherri Forest ](https://www.expedia.com/Madame-Sherri-Forest-Hotels.0-l553248621587477429-0.Travel-Guide-Filter-Hotels) - [Hotels near Madame Sherris Castle Ruins ](https://www.expedia.com/Madame-Sherris-Castle-Ruins-Hotels.0-l6273836-0.Travel-Guide-Filter-Hotels) - [Hotels near Chesterfield Gorge Natural Area ](https://www.expedia.com/Chesterfield-Gorge-Natural-Area-Hotels.0-l553248621587477426-0.Travel-Guide-Filter-Hotels) - [Hotels near Rhododendron State Park ](https://www.expedia.com/Rhododendron-State-Park-Hotels.0-l553248621532667357-0.Travel-Guide-Filter-Hotels) - [Hotels near Wantastiquet Mountain ](https://www.expedia.com/Wantastiquet-Mountain-Hotels.0-l553248635947261159-0.Travel-Guide-Filter-Hotels) - [Hotels near Spofford Lake ](https://www.expedia.com/Spofford-Lake-Hotels.0-l6265753-0.Travel-Guide-Filter-Hotels) - [Hotels near Dillant-Hopkins ](https://www.expedia.com/Dillant-Hopkins-Airport-Hotels.0-aEEN-0.Travel-Guide-Filter-Hotels) ### Flights - [Flights from Hinsdale ](https://www.expedia.com/lp/flights/3000447021/flights-from-hinsdale) - [Flights to Hinsdale ](https://www.expedia.com/Cheap-Flights-To-Hinsdale.d3000447021.Travel-Guide-Flights) - [Flights from Swanzey ](https://www.expedia.com/lp/flights/6348108/flights-from-swanzey) - [Flights to Swanzey ](https://www.expedia.com/Cheap-Flights-To-Swanzey.d6348108.Travel-Guide-Flights) - [Flights from Dillant-Hopkins ](https://www.expedia.com/lp/airports/een/flights-from-dillant-hopkins-airport) - [Flights from San Diego (SAN) to Keene (EEN) ](https://www.expedia.com/lp/flights/san/een/san-diego-to-keene) - [Flights from Manchester (MHT) to Keene (EEN) ](https://www.expedia.com/lp/flights/mht/een/manchester-to-keene) - [Flights from Boston (BOS) to Keene (EEN) ](https://www.expedia.com/lp/flights/bos/een/boston-to-keene) - [Flights from New York (NYC) to Keene (EEN) ](https://www.expedia.com/lp/flights/nyc/een/new-york-to-keene) - [Flights from Hartford (BDL) to Keene (EEN) ](https://www.expedia.com/lp/flights/bdl/een/hartford-to-keene) - [Flights from Portland (PDX) to Keene (EEN) ](https://www.expedia.com/lp/flights/pdx/een/portland-to-keene) - [Flights from Burlington (BTV) to Keene (EEN) ](https://www.expedia.com/lp/flights/btv/een/burlington-to-keene) - [Flights from Philadelphia (PHL) to Keene (EEN) ](https://www.expedia.com/lp/flights/phl/een/philadelphia-to-keene) - [Flights from Detroit (DTW) to Keene (EEN) ](https://www.expedia.com/lp/flights/dtw/een/detroit-to-keene) - [Flights from Orlando (MCO) to Keene (EEN) ](https://www.expedia.com/lp/flights/mco/een/orlando-to-keene) - [Flights from Denver (DEN) to Keene (EEN) ](https://www.expedia.com/lp/flights/den/een/denver-to-keene) - [Flights from Charlotte (CLT) to Keene (EEN) ](https://www.expedia.com/lp/flights/clt/een/charlotte-to-keene) - [Flights from Chicago (ORD) to Keene (EEN) ](https://www.expedia.com/lp/flights/ord/een/chicago-to-keene) - [Flights from Los Angeles (LAX) to Keene (EEN) ](https://www.expedia.com/lp/flights/lax/een/los-angeles-to-keene) - [Flights from Fort Myers (RSW) to Keene (EEN) ](https://www.expedia.com/lp/flights/rsw/een/fort-myers-to-keene) - [Flights from Washington (DCA) to Keene (EEN) ](https://www.expedia.com/lp/flights/dca/een/washington-to-keene) - [Flights from Baltimore (BWI) to Keene (EEN) ](https://www.expedia.com/lp/flights/bwi/een/baltimore-to-keene) - [Flights from Montreal (YUL) to Keene (EEN) ](https://www.expedia.com/lp/flights/yul/een/montreal-to-keene) - [Flights from San Francisco (SFO) to Keene (EEN) ](https://www.expedia.com/lp/flights/sfo/een/san-francisco-to-keene) - [Flights to Dillant-Hopkins ](https://www.expedia.com/Cheap-Flights-To-Dillant-Hopkins.d6027555.Travel-Guide-Flights) - [Flights from Tampa (TPA) to Keene (EEN) ](https://www.expedia.com/lp/flights/tpa/een/tampa-to-keene) - [Flights from Springfield (VSF) to Keene (EEN) ](https://www.expedia.com/lp/flights/vsf/een/springfield-to-keene) - [Flights from Buffalo (BUF) to Keene (EEN) ](https://www.expedia.com/lp/flights/buf/een/buffalo-to-keene) - [Flights from New York (LGA) to Keene (EEN) ](https://www.expedia.com/lp/flights/lga/een/new-york-to-keene) - [Flights from Cincinnati (CVG) to Keene (EEN) ](https://www.expedia.com/lp/flights/cvg/een/cincinnati-to-keene) - [Flights from Washington (IAD) to Keene (EEN) ](https://www.expedia.com/lp/flights/iad/een/washington-to-keene) - [Flights from Jacksonville (JAX) to Keene (EEN) ](https://www.expedia.com/lp/flights/jax/een/jacksonville-to-keene) - [Flights from West Palm Beach (PBI) to Keene (EEN) ](https://www.expedia.com/lp/flights/pbi/een/west-palm-beach-to-keene) - [Flights from Albany (ALB) to Keene (EEN) ](https://www.expedia.com/lp/flights/alb/een/albany-to-keene) - [Flights from Troy ](https://www.expedia.com/lp/flights/183587/flights-from-troy) - [Flights from Trenton (TTN) to Keene (EEN) ](https://www.expedia.com/lp/flights/ttn/een/trenton-to-keene) - [Flights from Milwaukee (MKE) to Keene (EEN) ](https://www.expedia.com/lp/flights/mke/een/milwaukee-to-keene) - [Flights from Louisville (SDF) to Keene (EEN) ](https://www.expedia.com/lp/flights/sdf/een/louisville-to-keene) - [Flights from Harrisburg (MDT) to Keene (EEN) ](https://www.expedia.com/lp/flights/mdt/een/harrisburg-to-keene) - [Flights from Chicago (MDW) to Keene (EEN) ](https://www.expedia.com/lp/flights/mdw/een/chicago-to-keene) - [Flights from Indianapolis (IND) to Keene (EEN) ](https://www.expedia.com/lp/flights/ind/een/indianapolis-to-keene) - [Flights from West Chesterfield ](https://www.expedia.com/lp/flights/183592/flights-from-west-chesterfield) ### Packages - [Visit Ashuelot ](https://www.expedia.com/Ashuelot.dx3000421398) - [Visit Hinsdale ](https://www.expedia.com/Hinsdale.dx3000447021) - [Visit Spofford ](https://www.expedia.com/Spofford.dx6267420) - [Visit Swanzey ](https://www.expedia.com/Swanzey.dx6348108) - [Visit Chesterfield ](https://www.expedia.com/Chesterfield.dx6052872) - [Madame Sherri Forest ](https://www.expedia.com/Madame-Sherri-Forest-West-Chesterfield.d553248621587477429.Vacation-Attraction) - [Madame Sherris Castle Ruins ](https://www.expedia.com/Madame-Sherris-Castle-Ruins-West-Chesterfield.d6273836.Vacation-Attraction) - [Rhododendron State Park ](https://www.expedia.com/Rhododendron-State-Park-New-Hampshire.d553248621532667357.Vacation-Attraction) - [Spofford Lake ](https://www.expedia.com/Spofford-Lake-Spofford.d6265753.Vacation-Attraction) ### Cars - [Car rentals near Hinsdale ](https://www.expedia.com/Car-Rentals-In-Hinsdale.d3000447021.Car-Rental-Guide) - [Car rentals near East Swanzey ](https://www.expedia.com/Car-Rentals-In-East-Swanzey.d553248635976384897.Car-Rental-Guide) - [Car rentals near Spofford ](https://www.expedia.com/Car-Rentals-In-Spofford.d6267420.Car-Rental-Guide) - [Car rentals near Swanzey ](https://www.expedia.com/Car-Rentals-In-Swanzey.d6348108.Car-Rental-Guide) - [Car rentals near Chesterfield ](https://www.expedia.com/Car-Rentals-In-Chesterfield.d6052872.Car-Rental-Guide) - [Car rentals near Madame Sherris Castle Ruins ](https://www.expedia.com/Car-Rentals-In-Madame-Sherris-Castle-Ruins.d6273836.Car-Rental-Guide) - [Car rentals near Rhododendron State Park ](https://www.expedia.com/Car-Rentals-In-Rhododendron-State-Park.d553248621532667357.Car-Rental-Guide) - [Car rentals near Spofford Lake ](https://www.expedia.com/Car-Rentals-In-Spofford-Lake.d6265753.Car-Rental-Guide) - [Car rental Swanzey Airport (EEN) ](https://www.expedia.com/Car-Rentals-In-Dillant-Hopkins.d6027555.Car-Rental-Guide) ### Vacation Rentals - [Ashuelot Vacation Rentals ](https://www.expedia.com/Ashuelot-Vacation-Rentals.d3000421398.Travel-Guide-VacationRentals) - [Spofford Vacation Rentals ](https://www.expedia.com/Spofford-Vacation-Rentals.d6267420.Travel-Guide-VacationRentals) \*Available to One Key members.