Flights To Cheshire County - Cheap Flights Starting at CA $490

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A street with historic buildings, a church steeple, and autumn foliage.

Keene

Flights
Keene

How Much Does it Cost To Fly To Cheshire County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Nov 6 - Fri, Nov 13
YYZ
Pearson Intl.
MHT
Manchester-Boston Regional
CA $918 Roundtrip, found 2 days ago
CA $918
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 6 from Pearson Intl. to Manchester-Boston Regional, returning Fri, Nov 13, priced at CA $918 found 2 days ago
Fri, Nov 6 - Fri, Nov 13
YYZ
Pearson Intl.
MHT
Manchester-Boston Regional
CA $968 Roundtrip, found 2 days ago
CA $968
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 6 from Pearson Intl. to Manchester-Boston Regional, returning Fri, Nov 13, priced at CA $968 found 2 days ago
Fri, Nov 6 - Fri, Nov 13
YYZ
Pearson Intl.
MHT
Manchester-Boston Regional
CA $994 Roundtrip, found 2 days ago
CA $994
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 6 from Pearson Intl. to Manchester-Boston Regional, returning Fri, Nov 13, priced at CA $994 found 2 days ago
Fri, Nov 6 - Fri, Nov 13
YYZ
Pearson Intl.
MHT
Manchester-Boston Regional
CA $1,020 Roundtrip, found 2 days ago
CA $1,020
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 6 from Pearson Intl. to Manchester-Boston Regional, returning Fri, Nov 13, priced at CA $1,020 found 2 days ago
Sat, Oct 17 - Thu, Nov 5
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $1,029 Roundtrip, found 6 days ago
CA $1,029
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Sat, Oct 17 from Pearson Intl. to Worcester Regional, returning Thu, Nov 5, priced at CA $1,029 found 6 days ago
Fri, Nov 6 - Fri, Nov 13
YYZ
Pearson Intl.
MHT
Manchester-Boston Regional
CA $1,045 Roundtrip, found 2 days ago
CA $1,045
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 6 from Pearson Intl. to Manchester-Boston Regional, returning Fri, Nov 13, priced at CA $1,045 found 2 days ago
Tue, Nov 24 - Sun, Nov 29
YYZ
Pearson Intl.
MHT
Manchester-Boston Regional
CA $1,054 Roundtrip, found 19 hours ago
CA $1,054
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Tue, Nov 24 from Pearson Intl. to Manchester-Boston Regional, returning Sun, Nov 29, priced at CA $1,054 found 19 hours ago
Fri, Nov 6 - Fri, Nov 13
YYZ
Pearson Intl.
MHT
Manchester-Boston Regional
CA $1,060 Roundtrip, found 2 days ago
CA $1,060
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 6 from Pearson Intl. to Manchester-Boston Regional, returning Fri, Nov 13, priced at CA $1,060 found 2 days ago
OriginDestinationTravel datesFlights from*
MCOLondonderryNovember 7 to November 11CA $259
TPALondonderryJanuary 15 to January 18CA $385
MCOWorcesterOctober 24 to October 31CA $614
LGAWorcesterOctober 30 to October 31CA $858
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
TPALondonderryOctober 16 to October 18CA $824
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn
2.0-star property

Deerfield Valley Inn

Oct 23 - Oct 26

3 night stay

Montreal (YUL) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was CA $1,322, price is now CA $1,257 per person
CA $1,257
per person
found 1 day ago
Sinclair Inn Bed and Breakfast
4.0-star property

Sinclair Inn Bed and Breakfast

Dec 19 - Dec 22

3 night stay

Toronto (YYZ) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,462, price is now CA $1,330 per person
CA $1,330
per person
found 1 day ago
1846 Inn and Tavern
3.0-star property

1846 Inn and Tavern

Oct 23 - Oct 26

3 night stay

Montreal (YUL) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was CA $1,583, price is now CA $1,489 per person
CA $1,489
per person
found 1 day ago
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Travelers ❤️ These Cheshire County 🏨

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Redfern Arts Center are located nearby.
Opens in a new windowBest Western Plus Keene Hotel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
7/10 Good! (1,002 reviews)
"The bed was very comfortable but the hotel was an absolute dirty dump!"

Reviewed on Oct 9, 2026

Opens in a new windowDays Inn by Wyndham Keene NH
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
8.6/10 Excellent! (1,002 reviews)
"The room was clean. Staff was very friendly. The breakfast was OK. Exactly what I needed."

Reviewed on Oct 10, 2026

Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
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Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive West Chesterfield NH
Book a stay at this business-friendly hotel in West Chesterfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Opens in a new windowRiverside Hotel, an Ascend Collection Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Cheshire County?
Travelers booked a roundtrip flight to Cheshire County for as little as CA $259 during the last seven days. If you find a bargain, act quick. Cheap deals don't stick around for long! This price was available on Travelocity for flights to Cheshire County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Cheshire County?
For your best chance at scoring a superb flight deal, time your vacation sometime during November. According to Travelocity's direct flight demand from January to December last year, it's the cheapest period to hop on a plane to Cheshire County.
How can I check my flight status to Cheshire County?
There are a few useful ways to track your flight status. You can find all the important info in our "Trips" portal, which is located at the top right of our homepage. Sign in or create a new account in seconds — you can then access and make changes to your bookings whenever you want to. For those on the go, the Travelocity app can also help you check the status of your flight to Cheshire County, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Cheshire County?
Here are our tips — book well in advance, avoid peak season and be flexible with your dates. If you don't have a specific date in mind, search for your flight to Cheshire County on Travelocity and click on "Flexible dates" above your results. This will help you find any cheaper tickets on a nearby day. CA $259 was the best price for a roundtrip flight to Cheshire County in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Cheshire County with Travelocity?
An awesome vacation is just a click away when you organize your trip with Travelocity. With competitive deals on cheap family flights, hotels, activities and rental cars, we make it simple to find the best prices for you. You can also use our 24/7 customer assistance and free cancellation policies on most hotels during every stage of the process. Wander with us and score your cheap flights to Cheshire County today.
What are the most popular flight routes to Cheshire County?
Whether you're organizing a short trip or a lengthy vacation, we can help you find your flight to Cheshire County. Main flight routes to this destination include:

  • Philadelphia, PA (PHL-Philadelphia Intl.) to Manchester-Boston Regional Airport (MHT) - 645 flights a month.
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Manchester-Boston Regional Airport (MHT) - 624 flights a month.
  • Washington, DC (IAD-Washington Dulles Intl.) to Manchester-Boston Regional Airport (MHT) - 424 flights a month.

How much is a flight to Cheshire County on average?
Get your next trip off to the best start by nabbing a fantastic deal with Travelocity. In the last seven days, roundtrip flights to Cheshire County cost between CA $259 and CA $1,060. Have a look at our site and lock in an airfare that's within your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.