Cheap Flights to Cheshire County from $52 (2026/2027)

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Keene

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Keene
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Jaffrey

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Jaffrey

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.

Thu, Jan 7 - Thu, Jan 14
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$112 Roundtrip, found 8 hours ago
$112
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Thu, Jan 7 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Jan 14, priced at $112 found 8 hours ago
Thu, Jan 7 - Thu, Jan 14
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jan 7 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Jan 14, priced at $117 found 6 days ago
Thu, Jan 21 - Thu, Jan 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$122 Roundtrip, found 13 hours ago
$122
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Jan 28, priced at $122 found 13 hours ago
Sun, Nov 8 - Thu, Nov 12
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$127 Roundtrip, found 6 days ago
$127
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Nov 8 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Nov 12, priced at $127 found 6 days ago
Wed, Oct 28 - Sat, Oct 31
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$155 Roundtrip, found 5 days ago
$155
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Oct 28 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Oct 31, priced at $155 found 5 days ago
Sat, Dec 5 - Sat, Dec 12
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$178 Roundtrip, found 4 days ago
$178
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Dec 5 from Southwest Florida Intl. to Manchester-Boston Regional, returning Sat, Dec 12, priced at $178 found 4 days ago
Tue, Jan 12 - Tue, Jan 19
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Jan 12 from Tampa Intl. to Manchester-Boston Regional, returning Tue, Jan 19, priced at $222 found 3 days ago
Sat, Oct 10 - Thu, Oct 15
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$257 Roundtrip, found 4 days ago
$257
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Oct 10 from Orlando Intl. to Manchester-Boston Regional, returning Thu, Oct 15, priced at $257 found 4 days ago
OriginDestinationTravel DatesFlights From*
RDULondonderryNovember 8 to November 12$127
MCOLondonderryOctober 28 to October 31$155
DCALondonderryOctober 14 to October 20$196
LGAWorcesterOctober 28 to October 29$213
TPALondonderrySeptember 13 to September 17$268
DENWorcesterSeptember 23 to September 30$272
MCOWorcesterNovember 5 to November 9$283
CLTWorcesterSeptember 10 to September 13$294
TPAWorcesterOctober 2 to October 13$295
PHLWorcesterSeptember 23 to September 29$299
ATLWorcesterSeptember 29 to October 6$307
DCAWorcesterSeptember 25 to September 27$308
CLTLondonderryNovember 2 to December 29$317
PHLLondonderrySeptember 30 to October 7$449
RDUWorcesterNovember 20 to November 22$637
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RDULondonderryAugust 30 to September 3$201
MCOLondonderryAugust 29 to September 2$346
DCALondonderryAugust 28 to August 30$409
TPALondonderryAugust 30 to September 6$425
CLTLondonderryAugust 29 to August 30$551
PHLLondonderryAugust 28 to August 30$560
MCOWorcesterAugust 29 to September 5$575
ATLWorcesterAugust 28 to August 30$589
PHLWorcesterAugust 28 to September 4$964
*Prices include taxes and fees

Best Cheshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Attitash Mountain Village
3.0-star property

Attitash Mountain Village

Sep 26 - Oct 2

6 night stay

Pittsburgh (PIT) to Manchester (MHT)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,284, price is now $749 per person
$749
per person
found 6 hours ago
The Village of Loon Mountain Fixed Rooms
2.0-star property

The Village of Loon Mountain Fixed Rooms

Sep 26 - Oct 2

6 night stay

Pittsburgh (PIT) to Manchester (MHT)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,416, price is now $929 per person
$929
per person
found 6 hours ago
The Village of Loon Mountain
3.0-star property

The Village of Loon Mountain

Sep 26 - Oct 2

6 night stay

Pittsburgh (PIT) to Manchester (MHT)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,246, price is now $908 per person
$908
per person
found 6 hours ago
Don't see what you're looking for?
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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.
8.6/10 Excellent! (1,013 reviews)
"The room was clean and stocked with the amenities expected, including a fridge and a microwave. Staff was very helpful and kind on check in. Breakfast was a standard continental. Not the best food but there was an array of options."

Reviewed on Aug 24, 2026

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! (1,006 reviews)
"Room was clean , but shower didn't work. Kleenex dispenser empty in bathroom. Too late and tired to call in someone to fix."

Reviewed on Aug 25, 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.
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 $112 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 January. 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. $112 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 $112 and $964. 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.
How long is the average flight to Cheshire County?
Below are a handful of leading direct flights to Cheshire County including their average flight duration:

  • Philadelphia, PA (PHL-Philadelphia Intl.) to Manchester-Boston Regional Airport (MHT) - 1 hour and 27 minutes
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Manchester-Boston Regional Airport (MHT) - 2 hours and 12 minutes
  • Washington, DC (IAD-Washington Dulles Intl.) to Manchester-Boston Regional Airport (MHT) - 1 hour and 41 minutes

What can I expect on a flight to Cheshire County?
That all depends on where you're leaving from and which air carrier you're traveling with. You'll likely find all sorts of flights to Cheshire County, from business class trips to cheap flights for family vacations. If a flight is classed as long haul, the airline will typically provide entertainment and hot meals as well as games for the youngsters.