Title:  Cheap Flights from Winchester - Expedia.ca

  

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# Cheap Flights from Winchester

-   [Roundtrip](?flightType=roundtrip)
-   [One-way](?flightType=oneway)
-   [Multi-city](?flightType=multicity)

### Travellers

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

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## 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
    

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## 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)

Tue, Oct 28 - Sat, Nov 1

BOS

Boston

ATL

Atlanta

CA $121

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ATL,departure:28/10/2025TANYT&leg2=from:ATL,to:BOS,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:120.86&airProductToken=AQpcCi0IzpYBEgQxMzAxGMGTASDlWii0yvsCMIPM-wI4UEAAWAFqAlJQcgZQQTE0TlIKKwjOlgESAzEzMBjlWiDgXCjxzfsCMObO-wI4UEABWAFqAlJQcgZQQTE0TlIKLwotCM6WARIEMTQ4MBjgXCDBkwEoy_r7AjDq-_sCOFVAAFgBagJTRHIGVUExNFYyEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Fri, Oct 31 - Sat, Nov 1

BOS

Boston

FLL

Fort Lauderdale

CA $122

Roundtrip

found 1 day ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:FLL,departure:31/10/2025TANYT&leg2=from:FLL,to:BOS,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:121.29&airProductToken=AQovCi0IzpYBEgQxMzAxGMGTASDlWijY7vsCMKrw-wI4R0AAWAFqAlJQcgZHQTE0TlIKLwotCM6WARIEMTMwMBjlWiDBkwEomvT7AjDe9fsCOEdAAFgBagJSUHIGR0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Mon, Oct 27 - Fri, Oct 31

BOS

Boston

MIA

Miami

CA $122

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:27/10/2025TANYT&leg2=from:MIA,to:BOS,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:121.29&airProductToken=AQovCi0IzpYBEgQxNjcwGMGTASCMAiiGwPsCMODB-wI4R0AAWAFqAlJQcgZHQTE0TlIKLwotCM6WARIEMTY2ORiMAiDBkwEoiOv7AjDM7PsCOEdAAFgBagJSUHIGR0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Mon, Nov 3 - Sat, Nov 8

BOS

Boston

MCO

Orlando

CA $135

Roundtrip

found 1 day ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MCO,departure:03/11/2025TANYT&leg2=from:MCO,to:BOS,departure:08/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:134.87&airProductToken=AQovCi0IzpYBEgQyMjAyGMGTASDMcCi3jfwCMPuO_AI4R0AAWAFqAlJQcgZHQTIxTlIKLwotCM6WARIEMjIwMRjMcCDBkwEoksT8AjDFxfwCOFdAAFgBagJSUHIGV0EyMVYyEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Mon, Oct 27 - Fri, Oct 31

BDL

Hartford

FLL

Fort Lauderdale

CA $151

Roundtrip

found 16 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BDL,to:FLL,departure:27/10/2025TANYT&leg2=from:FLL,to:BDL,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:150.59&airProductToken=AQotCisIzpYBEgQxNzQ3GOFYIOVaKI7B-wIwzML7AjhVQABYAWoCU0RyBVVBN05SCi4KLAjOlgESBDE3NDYY5Vog4Vgooez7AjDX7fsCOFVAAFgBagJTRHIGVUExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ)

![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif)

Wed, Oct 29 - Wed, Nov 5

PSM

Portsmouth

MCO

Orlando

CA $156

Roundtrip

found 1 day ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSM,to:MCO,departure:29/10/2025TANYT&leg2=from:MCO,to:PSM,departure:05/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:155.76&airProductToken=AQosCioIzbABEgM4NDcYz2QgzHAostT7AjCC1vsCOEJAAFgBagJOT3IFQk5PMDAKLAoqCM2wARIDODQ2GMxwIM9kKMSk_AIw-6X8AjhCQABYAWoCTk9yBUJOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ)

![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif)

Sat, Dec 6 - Sat, Dec 13

PSM

Portsmouth

RSW

Fort Myers

CA $156

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSM,to:RSW,departure:06/12/2025TANYT&leg2=from:RSW,to:PSM,departure:13/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:155.78&airProductToken=AQotCisIzbABEgM3ODEYz2Qg0bQBKMWD_wIwqoX_AjhBQABYAWoCTk9yBUFOTzAwCi0KKwjNsAESAzc4MBjRtAEgz2QoutD_AjD90f8COENAAFgBagJOT3IFQ05PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Wed, Nov 12 - Sat, Nov 15

BOS

Boston

TPA

Tampa

CA $164

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:TPA,departure:12/11/2025TANYT&leg2=from:TPA,to:BOS,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:163.20&airProductToken=AQoiCiAIwmwSBDExOTEYwZMBIPMDKJXy_AIw3fP8AjhMQABYAQogCh4IwmwSAjkyGPMDIMGTASiUkf0CMMOS_QI4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE)

![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif)

Mon, Dec 8 - Wed, Dec 17

BDL

Hartford

MCO

Orlando

CA $167

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MCO,departure:08/12/2025TANYT&leg2=from:MCO,to:BDL,departure:17/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:166.98&airProductToken=AQosCioIzbABEgM1NzgY4VggzHAotpf_AjDAmf8COEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDNTIzGMxwIOFYKP37_wIwpf3_AjhCQABYAWoCTk9yBUJOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ)

![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif)

Tue, Oct 28 - Tue, Nov 4

ALB

Albany

RSW

Fort Myers

CA $175

Roundtrip

found 1 day ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALB,to:RSW,departure:28/10/2025TANYT&leg2=from:RSW,to:ALB,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:174.53&airProductToken=AQotCisIzbABEgM3NDUY4Aog0bQBKMHJ-wIw2sv7AjhCQABYAWoCTk9yBUJOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ)

![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif)

Sat, Jan 31 - Sat, Feb 7

MHT

Manchester

MCO

Orlando

CA $178

Roundtrip

found 18 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MHT,to:MCO,departure:31/01/2026TANYT&leg2=from:MCO,to:MHT,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:177.16&airProductToken=AQotCisIzbABEgM4MTcY7JkBIMxwKNn5gwMwq_uDAzhCQABYAWoCTk9yBUJOTzAwCi0KKwjNsAESAzgxNhjMcCDsmQEo0caEAzCRyIQDOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN)

![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif)

Sun, Dec 7 - Thu, Dec 11

ALB

Albany

MCO

Orlando

CA $183

Roundtrip

found 2 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALB,to:MCO,departure:07/12/2025TANYT&leg2=from:MCO,to:ALB,departure:11/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:182.42&airProductToken=AQosCioIzbABEgM4NTUY4AogzHAokYz_AjCVjv8COEVAAFgBagJOT3IFRU5PMDAKLAoqCM2wARIDODU0GMxwIOAKKO-2_wIw6bj_AjhCQABYAWoCTk9yBUJOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Fri, Jan 23 - Mon, Jan 26

BDL

Hartford

TPA

Tampa

CA $192

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BDL,to:TPA,departure:23/01/2026TANYT&leg2=from:TPA,to:BDL,departure:26/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:191.20&airProductToken=AQouCiwIwmwSAzUzMxjhWCDzAyismoMDMO2bgwM4TEAAWAFqAkROcghQSTJRVUVMMQovCi0IwmwSBDE1MzQY8wMg4Vgo4L6DAzCGwIMDOExAAFgBagJETnIIUEkyUVVFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Mon, Nov 10 - Thu, Nov 13

BOS

Boston

RSW

Fort Myers

CA $192

Roundtrip

found 1 day ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:RSW,departure:10/11/2025TANYT&leg2=from:RSW,to:BOS,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:191.20&airProductToken=AQokCiIIxJgBEgQyNDU0GMGTASDRtAEopN38AjCB3_wCOEVAAFgBCiQKIgjEmAESBDI0NTQY0bQBIMGTASiagf0CMNWC_QI4RUAAWAESCggBEAEYASoCREwYASIECAEQASgEMAE)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Mon, Dec 8 - Mon, Dec 15

ALB

Albany

FLL

Fort Lauderdale

CA $195

Roundtrip

found 6 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALB,to:FLL,departure:08/12/2025TANYT&leg2=from:FLL,to:ALB,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:194.40&airProductToken=AQovCi0IwmwSBDEwODcY4Aog5Voo7JT_AjC0lv8COExAAFgBagJETnIIUEkyUVJFTDEKLwotCMJsEgQxMDg4GOVaIOAKKKTo_wIw2en_AjhMQABYAWoCRE5yCFBJMlFSRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Thu, Jan 22 - Thu, Jan 29

MHT

Manchester

RSW

Fort Myers

CA $200

Roundtrip

found 12 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MHT,to:RSW,departure:22/01/2026TANYT&leg2=from:RSW,to:MHT,departure:29/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:199.80&airProductToken=AQoxCi8IwmwSBDEzNDkY7JkBING0ASjOkoMDMKmUgwM4TEAAWAFqAkROcghQSTJRUkVMMQoxCi8IwmwSBDEzNTAY0bQBIOyZASjB44MDMIDlgwM4TEAAWAFqAkROcghQSTJRUkVMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Thu, Oct 23 - Fri, Oct 31

BOS

Boston

LAS

Las Vegas

CA $204

Roundtrip

found 6 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:LAS,departure:23/10/2025TANYT&leg2=from:LAS,to:BOS,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:203.98&airProductToken=AQpbCiwIzpYBEgQyMzAxGMGTASChAyiRkfsCMLiS-wI4VUAAWAFqAlNEcgVVQTdOUgorCM6WARIDMTIxGKEDIIuQASi7lPsCMK-W-wI4VUABWAFqAlNEcgVVQTdOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Mon, Nov 24 - Wed, Dec 3

PVD

Providence

FLL

Fort Lauderdale

CA $207

Roundtrip

found 6 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PVD,to:FLL,departure:24/11/2025TANYT&leg2=from:FLL,to:PVD,departure:03/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:206.20&airProductToken=AQouCiwIwmwSAzU5NxivHSDlWij39v0CMLj4_QI4TEAAWAFqAkROcghQSTdRQkVMMQovCi0IwmwSBDExOTYY5Vogrx0ortz-AjDe3f4COExAAFgBagJETnIIUEkyUVVFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Fri, Oct 31 - Fri, Nov 7

MHT

Manchester

FLL

Fort Lauderdale

CA $212

Roundtrip

found 9 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MHT,to:FLL,departure:31/10/2025TANYT&leg2=from:FLL,to:MHT,departure:07/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:211.60&airProductToken=AQowCi4IwmwSBDEzNDMY7JkBIOVaKKjs-wIw8u37AjhMQABYAWoCRE5yCFBJNFFSRUwxCjAKLgjCbBIEMTM0NBjlWiDsmQEojL38AjDHvvwCOExAAFgBagJETnIIUEk0UVJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB)

![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif)

Tue, Oct 28 - Tue, Nov 4

BDL

Hartford

RSW

Fort Myers

CA $217

Roundtrip

found 8 hours ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BDL,to:RSW,departure:28/10/2025TANYT&leg2=from:RSW,to:BDL,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:216.69&airProductToken=AQppCjIIwYIBEgQyNjIyGOFYIOKaASjlyPsCMOXJ-wI4QkAAWAFqBUJBU0lDcghPVUFKWlNCVgozCMGCARIEMTkzMBjimgEg0bQBKOnK-wIw3cv7AjhCQAFYAWoFQkFTSUNyCE9VQUpaU0JWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw)

## Flights from Winchester: Essential Travel Information

| Cheapest flight from Winchester | CA $121 (roundtrip) |
| --- | --- |
| Best airlines to fly from Winchester | Spirit Airlines, Breeze Airways, JetBlue Airways, Delta, American Airlines |
| Cheapest month to fly from Winchester | October |
| Winchester IATA code | EEN |
| Winchester Country/State | New Hampshire |
| Airline ticket deals from Winchester | CA $121 - CA $217 |

## 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 $121. You'll often find the best deals in October. 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 $121. 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, Breeze Airways, JetBlue Airways, Delta, American Airlines. 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 October, 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 $121 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 October 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 $121 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.