Flights To Cheshire County - Cheap Flights Starting at CA $93

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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.

Wed, Nov 4 - Sat, Nov 14
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $219 Roundtrip, found 1 day ago
CA $219
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Nov 4 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at CA $219 found 1 day ago
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $237 Roundtrip, found 2 hours ago
CA $237
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Dec 5 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Dec 12, priced at CA $237 found 2 hours ago
Sat, Sep 12 - Sat, Sep 19
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $256 Roundtrip, found 2 days ago
CA $256
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Sep 12 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Sep 19, priced at CA $256 found 2 days ago
Wed, Nov 4 - Sat, Nov 14
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $319 Roundtrip, found 1 day ago
CA $319
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at CA $319 found 1 day ago
Wed, Nov 4 - Sat, Nov 14
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $319 Roundtrip, found 1 day ago
CA $319
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Nov 4 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at CA $319 found 1 day ago
Sat, Sep 12 - Sat, Sep 19
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $344 Roundtrip, found 2 days ago
CA $344
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Sep 19, priced at CA $344 found 2 days ago
Sat, Sep 12 - Sat, Sep 19
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $345 Roundtrip, found 2 days ago
CA $345
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 12 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Sep 19, priced at CA $345 found 2 days ago
Thu, Nov 12 - Mon, Nov 16
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
CA $382 Roundtrip, found 2 days ago
CA $382
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Nov 12 from Tampa Intl. to Manchester-Boston Regional, returning Mon, Nov 16, priced at CA $382 found 2 days ago
Mon, Sep 21 - Mon, Sep 28
YOW
Macdonald-Cartier Intl.
ORH
Worcester Regional
CA $891 Roundtrip, found 1 day ago
CA $891
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Sep 21 from Macdonald-Cartier Intl. to Worcester Regional, returning Mon, Sep 28, priced at CA $891 found 1 day ago
Mon, Sep 21 - Mon, Sep 28
YOW
Macdonald-Cartier Intl.
ORH
Worcester Regional
CA $904 Roundtrip, found 1 day ago
CA $904
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Sep 21 from Macdonald-Cartier Intl. to Worcester Regional, returning Mon, Sep 28, priced at CA $904 found 1 day ago
Mon, Sep 21 - Mon, Sep 28
YOW
Macdonald-Cartier Intl.
ORH
Worcester Regional
CA $936 Roundtrip, found 1 day ago
CA $936
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Sep 21 from Macdonald-Cartier Intl. to Worcester Regional, returning Mon, Sep 28, priced at CA $936 found 1 day ago
Mon, Sep 21 - Mon, Sep 28
YOW
Macdonald-Cartier Intl.
ORH
Worcester Regional
CA $984 Roundtrip, found 1 day ago
CA $984
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Sep 21 from Macdonald-Cartier Intl. to Worcester Regional, returning Mon, Sep 28, priced at CA $984 found 1 day ago
OriginDestinationTravel datesFlights from*
MCOLondonderryNovember 4 to November 14CA $219
TPALondonderryNovember 12 to November 16CA $382
ATLWorcesterNovember 6 to November 8CA $429
RDULondonderrySeptember 10 to September 13CA $482
MCOWorcesterOctober 14 to October 18CA $530
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt.Sunapee
2.0-star property

Hideaway Inn Mt.Sunapee

Aug 27 - Aug 31

4 night stay

Montreal (YMQ) to Manchester (MHT)

Porter Airlines • Roundtrip • Coach
Price was CA $1,270, price is now CA $1,080 per person
CA $1,080
per person
found 1 day ago
Cold Spring Plymouth Resort
3.5-star property

Cold Spring Plymouth Resort

Oct 9 - Oct 13

4 night stay

Detroit (DTT) to Manchester (MHT)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,526, price is now CA $1,259 per person
CA $1,259
per person
found 21 hours ago
Mountain View Grand Resort & Spa
4.0-star property

Mountain View Grand Resort & Spa

Aug 27 - Aug 31

4 night stay

Montreal (YMQ) to Manchester (MHT)

Porter Airlines • Roundtrip • Coach
Price was CA $1,724, price is now CA $1,424 per person
CA $1,424
per person
found 1 day ago
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Travelers ❤️ These Cheshire County 🏨

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.
Opens in a new windowKeene Elm City Hotel, an Ascend Collection 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! (1,004 reviews)
"The room smelled of mold and urine and the floor carpet felt wet. Would not recommend this property."

Reviewed on Aug 22, 2026

Opens in a new windowDays Inn by Wyndham Keene NH
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
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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.
9.6/10 Exceptional! (679 reviews)
"Over all, pleasant stay. The balcony and balcony chairs need regular cleaning. Room and bathroom were fine. No coffee downstairs. Cheese and crackers, chips or candy available for sale at the desk or a vending machine would be nice."

Reviewed on Aug 18, 2026

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 $219 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 $219 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 $219 and CA $984. 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.