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

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A street with historic buildings, a church steeple, and autumn foliage.

Keene

Flights
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 - Tue, Jan 26
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jan 21 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Tue, Jan 26, priced at $112 found 5 days ago
Thu, Jan 7 - Thu, Jan 14
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 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 4 days ago
Thu, Jan 21 - Thu, Jan 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$122 Roundtrip, found 9 hours ago
$122
Roundtrip
found 9 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 9 hours ago
Sun, Nov 8 - Thu, Nov 12
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 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 4 days ago
Wed, Oct 28 - Sat, Oct 31
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$155 Roundtrip, found 3 days ago
$155
Roundtrip
found 3 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 3 days ago
Fri, Nov 6 - Mon, Nov 16
MYR
Myrtle Beach Intl.
MHT
Manchester-Boston Regional
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Nov 6 from Myrtle Beach Intl. to Manchester-Boston Regional, returning Mon, Nov 16, priced at $193 found 1 day ago
Tue, Jan 12 - Tue, Jan 19
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jan 12 from Tampa Intl. to Manchester-Boston Regional, returning Tue, Jan 19, priced at $222 found 1 day ago
Sat, Oct 10 - Thu, Oct 15
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 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 2 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
TPALondonderryNovember 8 to November 16$229
DENWorcesterSeptember 23 to September 30$272
MCOWorcesterNovember 5 to November 9$283
CLTWorcesterSeptember 19 to September 20$290
TPAWorcesterOctober 2 to October 13$295
PHLWorcesterSeptember 23 to September 29$299
CLTLondonderryNovember 2 to December 29$317
RDUWorcesterOctober 14 to October 18$327
DCAWorcesterSeptember 6 to September 12$357
PHLLondonderrySeptember 30 to October 7$449
LGALondonderrySeptember 14 to September 18$478
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RDULondonderryAugust 30 to September 3$201
TPALondonderryAugust 28 to September 5$334
DCALondonderryAugust 28 to August 30$409
MCOLondonderryAugust 29 to August 30$430
MCOWorcesterAugust 30 to September 6$438
DCAWorcesterAugust 28 to August 31$452
CLTLondonderryAugust 29 to September 5$476
PHLLondonderryAugust 30 to September 6$504
DENLondonderryAugust 30 to August 31$534
PHLWorcesterAugust 28 to September 4$964
ATLWorcesterAugust 28 to August 30$1,025
*Prices include taxes and fees

Best Cheshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Aurora Inn & Cottages
2.0-star property

The Aurora Inn & Cottages

Oct 16 - Oct 18

2 night stay

Pittsburgh (PIT) to Manchester (MHT)

JetBlue Airways • Non-stop roundtrip • Coach
Price was $715, price is now $553 per person
$553
per person
found 1 day ago
Mountain View Grand Resort & Spa
4.0-star property

Mountain View Grand Resort & Spa

Sep 2 - Sep 7

5 night stay

Austin (AUS) to Manchester (MHT)

American Airlines • Non-stop • Coach

Manchester (MHT) to Austin (AUS)

JetBlue Airways • Non-stop • Coach
Price was $1,441, price is now $1,081 per person
$1,081
per person
found 1 day ago
The Shire Woodstock
3.0-star property

The Shire Woodstock

Oct 22 - Oct 25

3 night stay

Pittsburgh (PIT) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,603, price is now $1,212 per person
$1,212
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 $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 $1,025. 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.