Flights To Cheshire County - Cheap Flights Starting at CA $238

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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.

Tue, Jun 16 - Wed, Jun 17
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $538 Roundtrip, found 4 hours ago
CA $538
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Worcester Regional, returning Wed, Jun 17, priced at CA $538 found 4 hours ago
Tue, Jun 16 - Wed, Jun 17
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $580 Roundtrip, found 4 hours ago
CA $580
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Worcester Regional, returning Wed, Jun 17, priced at CA $580 found 4 hours ago
Tue, Jun 16 - Wed, Jun 17
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $585 Roundtrip, found 4 hours ago
CA $585
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Worcester Regional, returning Wed, Jun 17, priced at CA $585 found 4 hours ago
Tue, Jun 16 - Wed, Jun 17
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $594 Roundtrip, found 4 hours ago
CA $594
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Worcester Regional, returning Wed, Jun 17, priced at CA $594 found 4 hours ago
Tue, Jun 16 - Wed, Jun 17
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $641 Roundtrip, found 4 hours ago
CA $641
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Worcester Regional, returning Wed, Jun 17, priced at CA $641 found 4 hours ago
Tue, Jun 16 - Wed, Jun 17
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $649 Roundtrip, found 4 hours ago
CA $649
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Worcester Regional, returning Wed, Jun 17, priced at CA $649 found 4 hours ago
Tue, Jun 16 - Wed, Jun 17
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $678 Roundtrip, found 4 hours ago
CA $678
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Worcester Regional, returning Wed, Jun 17, priced at CA $678 found 4 hours ago
Tue, Jun 16 - Wed, Jun 17
YYZ
Pearson Intl.
ORH
Worcester Regional
CA $691 Roundtrip, found 4 hours ago
CA $691
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Worcester Regional, returning Wed, Jun 17, priced at CA $691 found 4 hours 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
The Inn at Thorn Hill & Spa
4.0-star property

The Inn at Thorn Hill & Spa

Jun 6 - Jun 9

3 night stay

Toronto (YYZ) to Manchester (MHT)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,364, price is now CA $1,190 per person
CA $1,190
per person
found 24 hours 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.
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
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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 June. 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 $691. 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.