Flights To Cheshire County - Cheap Flights Starting at CA $471

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Cheshire County's top cities

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.

Mon, Aug 17 - Thu, Aug 20
YVR
Vancouver Intl.
MHT
Manchester-Boston Regional
CA $877 Roundtrip, found 1 day ago
CA $877
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 17 from Vancouver Intl. to Manchester-Boston Regional, returning Thu, Aug 20, priced at CA $877 found 1 day ago
Fri, Jul 17 - Thu, Jul 30
YVR
Vancouver Intl.
MHT
Manchester-Boston Regional
CA $879 Roundtrip, found 18 hours ago
CA $879
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Fri, Jul 17 from Vancouver Intl. to Manchester-Boston Regional, returning Thu, Jul 30, priced at CA $879 found 18 hours ago
Mon, Aug 17 - Thu, Aug 20
YVR
Vancouver Intl.
MHT
Manchester-Boston Regional
CA $919 Roundtrip, found 1 day ago
CA $919
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 17 from Vancouver Intl. to Manchester-Boston Regional, returning Thu, Aug 20, priced at CA $919 found 1 day ago
Mon, Aug 17 - Thu, Aug 20
YVR
Vancouver Intl.
MHT
Manchester-Boston Regional
CA $921 Roundtrip, found 1 day ago
CA $921
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 17 from Vancouver Intl. to Manchester-Boston Regional, returning Thu, Aug 20, priced at CA $921 found 1 day ago
Fri, Jul 17 - Thu, Jul 30
YVR
Vancouver Intl.
MHT
Manchester-Boston Regional
CA $963 Roundtrip, found 18 hours ago
CA $963
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Fri, Jul 17 from Vancouver Intl. to Manchester-Boston Regional, returning Thu, Jul 30, priced at CA $963 found 18 hours ago
Mon, Aug 17 - Thu, Aug 20
YVR
Vancouver Intl.
MHT
Manchester-Boston Regional
CA $1,005 Roundtrip, found 1 day ago
CA $1,005
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 17 from Vancouver Intl. to Manchester-Boston Regional, returning Thu, Aug 20, priced at CA $1,005 found 1 day ago
Mon, Aug 17 - Thu, Aug 20
YVR
Vancouver Intl.
MHT
Manchester-Boston Regional
CA $1,009 Roundtrip, found 1 day ago
CA $1,009
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 17 from Vancouver Intl. to Manchester-Boston Regional, returning Thu, Aug 20, priced at CA $1,009 found 1 day ago
Mon, Mar 15 - Fri, Mar 19
YVR
Vancouver Intl.
MHT
Manchester-Boston Regional
CA $1,013 Roundtrip, found 1 day ago
CA $1,013
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Mar 15 from Vancouver Intl. to Manchester-Boston Regional, returning Fri, Mar 19, priced at CA $1,013 found 1 day ago
OriginDestinationTravel datesFlights from*
MCOLondonderryJune 17 to June 29CA $299
TPAWorcesterJuly 16 to July 20CA $446
RDULondonderryAugust 6 to August 16CA $453
DCAWorcesterJune 11 to June 13CA $573
CLTLondonderryJune 29 to July 4CA $664
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCOLondonderryMay 30 to June 6CA $312
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Grand Summit Resort, A Vail Resorts Property
3.0-star property

Grand Summit Resort, A Vail Resorts Property

Aug 2 - Aug 9

7 night stay

Toronto (YYZ) to Springfield (VSF)

Air Canada • Roundtrip • Coach
Price was CA $1,196, price is now CA $1,004 per person
CA $1,004
per person
found 1 day ago
Latchis Hotel
2.5-star property

Latchis Hotel

Aug 2 - Aug 9

7 night stay

Toronto (YYZ) to Springfield (VSF)

Air Canada • Roundtrip • Coach
Price was CA $1,319, price is now CA $1,009 per person
CA $1,009
per person
found 1 day ago
Chalet 239
2.0-star property

Chalet 239

Jun 30 - Jul 5

5 night stay

Toronto (YYZ) to Springfield (VSF)

Delta • Non-stop roundtrip • Coach
Price was CA $1,351, price is now CA $1,144 per person
CA $1,144
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Toronto to Cheshire County
View all trips

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.
8.4/10 Very Good! (1,001 reviews)
"Bueno"

Reviewed on May 22, 2026

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! (1,000 reviews)
"The property was ok. It was an older property and I get that. The property owners were polite and nice. It needs a clean up and refurbished. My room was missing two florescent light bulbs in the bathroom. There was only one dull bulbs in the bathroom. I had to soap up and shave in the mirror in the ..."

Reviewed on May 20, 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! (1,004 reviews)
"Really friendly, helpful and accommodating staff. Clean and well maintained. Would definitely stay here again!"

Reviewed on May 20, 2026

Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
8.8/10 Excellent! (385 reviews)
"Clean rooms, good location, easy parking, excellent service!"

Reviewed on May 7, 2026

Opens in a new windowHampton Inn & Suites Keene
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 $299 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 August. 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 $299 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 $299 and CA $1,013. 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.