Cheap Flights to Cheshire County from $56 (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 21 - Sun, Jan 24
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$112 Roundtrip, found 4 hours ago
$112
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Jan 24, priced at $112 found 4 hours ago
Thu, Jan 21 - Thu, Jan 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$117 Roundtrip, found 15 hours ago
$117
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Jan 28, priced at $117 found 15 hours ago
Thu, Jan 21 - Thu, Jan 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$122 Roundtrip, found 15 hours ago
$122
Roundtrip
found 15 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 15 hours ago
Wed, Dec 9 - Wed, Dec 16
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$137 Roundtrip, found 22 hours ago
$137
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Wed, Dec 9 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Dec 16, priced at $137 found 22 hours ago
Wed, Jan 27 - Tue, Feb 2
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jan 27 from Southwest Florida Intl. to Manchester-Boston Regional, returning Tue, Feb 2, priced at $153 found 1 day ago
Tue, Nov 10 - Wed, Nov 11
FLL
Fort Lauderdale - Hollywood Intl.
MHT
Manchester-Boston Regional
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Nov 10 from Fort Lauderdale - Hollywood Intl. to Manchester-Boston Regional, returning Wed, Nov 11, priced at $173 found 1 day ago
Thu, Dec 3 - Sat, Dec 12
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Dec 3 from Southwest Florida Intl. to Manchester-Boston Regional, returning Sat, Dec 12, priced at $207 found 1 day ago
Thu, Dec 3 - Sat, Dec 12
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Dec 3 from Southwest Florida Intl. to Manchester-Boston Regional, returning Sat, Dec 12, priced at $207 found 1 day ago
Fri, Jan 8 - Sun, Jan 17
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa Intl. to Manchester-Boston Regional, returning Sun, Jan 17, priced at $209 found 2 days ago
Wed, Nov 4 - Wed, Nov 11
CLT
Charlotte-Douglas Intl.
MHT
Manchester-Boston Regional
$325 Roundtrip, found 15 hours ago
$325
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Charlotte-Douglas Intl. to Manchester-Boston Regional, returning Wed, Nov 11, priced at $325 found 15 hours ago
OriginDestinationTravel DatesFlights From*
RDULondonderryJanuary 12 to January 17$107
TPALondonderryJanuary 8 to January 17$209
DCALondonderryNovember 23 to November 24$225
ATLLondonderryNovember 14 to November 17$257
TPAWorcesterNovember 4 to November 5$272
DCAWorcesterNovember 19 to November 22$287
LGAWorcesterOctober 26 to October 30$297
CLTLondonderryNovember 4 to November 11$325
ATLWorcesterOctober 26 to October 30$335
PHLLondonderryDecember 11 to December 14$366
MCOWorcesterDecember 4 to December 7$366
DENWorcesterOctober 29 to November 1$372
CLTWorcesterOctober 26 to October 29$389
RDUWorcesterDecember 23 to December 28$392
PHLWorcesterOctober 29 to October 31$466
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DCALondonderryOctober 10 to October 17$364
LGAWorcesterOctober 11 to October 12$384
MCOWorcesterOctober 11 to October 19$407
MCOLondonderryOctober 10 to October 17$409
TPALondonderryOctober 11 to December 8$489
DCAWorcesterOctober 10 to October 13$506
RDULondonderryOctober 11 to October 15$509
ATLLondonderryOctober 11 to October 15$575
CLTLondonderryOctober 10 to October 12$599
PHLLondonderryOctober 10 to October 12$608
DENLondonderryOctober 11 to October 18$734
PHLWorcesterOctober 10 to October 18$800
LGALondonderryOctober 10 to October 11$861
*Prices include taxes and fees

Best Cheshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts Pollard Brook
3.0-star property

InnSeason Resorts Pollard Brook

Nov 10 - Nov 14

4 night stay

Dallas (DFW) to Manchester (MHT)

Delta • Roundtrip • Coach
Price was $649, price is now $508 per person
$508
per person
found 1 day ago
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Jan 2 - Jan 9

7 night stay

Dallas (DFW) to Springfield (VSF)

American Airlines • Non-stop • Coach

Springfield (VSF) to Dallas (DFW)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,779, price is now $1,330 per person
$1,330
per person
found 6 hours ago
1846 Inn and Tavern
3.0-star property

1846 Inn and Tavern

Jan 2 - Jan 9

7 night stay

Dallas (DFW) to Springfield (VSF)

American Airlines • Non-stop • Coach

Springfield (VSF) to Dallas (DFW)

Southwest Airlines • Non-stop • Coach
Price was $1,487, price is now $1,165 per person
$1,165
per person
found 6 hours ago
Don't see what you're looking for?
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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.
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.
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.
9.6/10 Exceptional! (693 reviews)
"great views of the river and the room was very clean. Strange parking lot, Everyone at the hotel was very helpful 9/10"

Reviewed on Oct 8, 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 $107 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. $107 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 $107 and $861. 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.