Cheap Flights to Cheshire County from $61 (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.

Tue, Dec 8 - Tue, Dec 15
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Dec 8 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Tue, Dec 15, priced at $132 found 6 days ago
Tue, Jan 12 - Tue, Jan 19
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Jan 12 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Tue, Jan 19, priced at $137 found 5 days ago
Thu, Jan 21 - Thu, Jan 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jan 21 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Jan 28, priced at $142 found 1 day ago
Sun, Aug 23 - Thu, Aug 27
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$146 Roundtrip, found 4 days ago
$146
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Aug 23 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Aug 27, priced at $146 found 4 days ago
Wed, Sep 30 - Sat, Oct 3
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$150 Roundtrip, found 14 hours ago
$150
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Wed, Sep 30 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Oct 3, priced at $150 found 14 hours ago
Thu, Sep 17 - Thu, Oct 15
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$217 Roundtrip, found 22 hours ago
$217
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Thu, Sep 17 from Tampa Intl. to Manchester-Boston Regional, returning Thu, Oct 15, priced at $217 found 22 hours ago
Sat, Aug 15 - Tue, Aug 18
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$234 Roundtrip, found 5 hours ago
$234
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Aug 15 from Orlando Intl. to Manchester-Boston Regional, returning Tue, Aug 18, priced at $234 found 5 hours ago
Wed, Sep 9 - Sat, Sep 12
PNS
Pensacola Intl.
MHT
Manchester-Boston Regional
$239 Roundtrip, found 14 hours ago
$239
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, Sep 9 from Pensacola Intl. to Manchester-Boston Regional, returning Sat, Sep 12, priced at $239 found 14 hours ago
OriginDestinationTravel DatesFlights From*
MCOLondonderrySeptember 23 to October 3$150
LGAWorcesterAugust 4 to August 7$156
DCALondonderryAugust 26 to September 1$193
TPALondonderrySeptember 17 to October 15$217
DCAWorcesterAugust 27 to August 29$248
ATLLondonderrySeptember 17 to September 22$258
MCOWorcesterSeptember 19 to September 26$272
DENWorcesterAugust 7 to August 15$279
DENLondonderrySeptember 12 to September 17$281
CLTLondonderryAugust 17 to August 31$289
TPAWorcesterJuly 24 to July 26$319
PHLLondonderryAugust 31 to September 3$355
PHLWorcesterAugust 10 to August 17$357
CLTWorcesterOctober 14 to October 17$398
ATLWorcesterJuly 22 to July 29$528
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RDULondonderryJuly 12 to July 23$287
LGAWorcesterJuly 10 to July 12$338
DCALondonderryJuly 11 to July 13$346
MCOWorcesterJuly 10 to July 15$382
MCOLondonderryJuly 12 to July 17$417
TPALondonderryJuly 10 to November 12$464
DCAWorcesterJuly 10 to July 14$466
CLTLondonderryJuly 11 to July 16$546
ATLLondonderryJuly 12 to July 14$617
PHLLondonderryJuly 12 to July 14$777
ATLWorcesterJuly 10 to July 12$1,258
*Prices include taxes and fees

Best Cheshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Village of Loon Mountain Fixed Rooms
2.0-star property

The Village of Loon Mountain Fixed Rooms

Sep 11 - Sep 13

2 night stay

Baltimore (BWI) to Manchester (MHT)

Delta • Coach

Manchester (MHT) to Baltimore (BWI)

Southwest Airlines • Coach
Price was $534, price is now $393 per person
$393
per person
found 16 hours ago
The Centennial
4.0-star property

The Centennial

Sep 17 - Sep 24

7 night stay

Orlando (MCO) to Manchester (MHT)

Breeze Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,293, price is now $764 per person
$764
per person
found 1 day ago
Exeter Inn
3.5-star property

Exeter Inn

Oct 2 - Oct 5

3 night stay

Philadelphia (PHL) to Manchester (MHT)

JetBlue Airways • Roundtrip • Coach
Price was $672, price is now $506 per person
$506
per person
found 1 day ago
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See all available trips from Baltimore to Cheshire County
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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! (1,010 reviews)
"The only thing we didn’t like was the mattress. Not firm enough."

Reviewed on Jul 6, 2026

Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
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! (1,006 reviews)
"Great staff. Clean and comfortable. Fantastic breakfast. Loved the Andes mints."

Reviewed on Jul 6, 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! (1,004 reviews)
"Pros: + Air conditioned + Free parking + Free breakfast + Free wifi + Nice people + Cheapest hotel in Keene Cons: - Half of the outlets in the room didn't work - No pool Overall a good deal."

Reviewed on Jul 7, 2026

Opens in a new windowDays Inn by Wyndham Keene NH
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Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonial Theatre and Central Square are located nearby.
8.6/10 Excellent! (1,002 reviews)
"Perfect location"

Reviewed on Jul 5, 2026

Opens in a new windowCourtyard by Marriott Keene Downtown
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 $132 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 December. 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. $132 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 $132 and $1,258. 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.