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.

Wed, Sep 16 - Sat, Sep 19
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 16 from Southwest Florida Intl. to Manchester-Boston Regional, returning Sat, Sep 19, priced at $127 found 1 day ago
Tue, Jan 26 - Sun, Jan 31
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jan 26 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Jan 31, priced at $137 found 1 day ago
Thu, Mar 4 - Tue, Mar 9
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$142 Roundtrip, found 1 hour ago
$142
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Mar 4 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Tue, Mar 9, priced at $142 found 1 hour ago
Wed, Sep 16 - Sat, Sep 19
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$142 Roundtrip, found 5 days ago
$142
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Sep 16 from Southwest Florida Intl. to Manchester-Boston Regional, returning Sat, Sep 19, priced at $142 found 5 days ago
Wed, Sep 16 - Sat, Sep 26
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$146 Roundtrip, found 9 hours ago
$146
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Sep 26, priced at $146 found 9 hours ago
Sun, Nov 8 - Sun, Nov 15
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$147 Roundtrip, found 8 hours ago
$147
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Sun, Nov 8 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Nov 15, priced at $147 found 8 hours ago
Fri, Oct 9 - Tue, Oct 13
FLL
Fort Lauderdale - Hollywood Intl.
MHT
Manchester-Boston Regional
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Oct 9 from Fort Lauderdale - Hollywood Intl. to Manchester-Boston Regional, returning Tue, Oct 13, priced at $167 found 5 days ago
Fri, Jul 24 - Fri, Jul 31
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$229 Roundtrip, found 5 days ago
$229
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jul 24 from Orlando Intl. to Manchester-Boston Regional, returning Fri, Jul 31, priced at $229 found 5 days ago
Thu, Aug 13 - Sat, Aug 22
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 13 from Tampa Intl. to Manchester-Boston Regional, returning Sat, Aug 22, priced at $250 found 1 day ago
Fri, Oct 2 - Sun, Oct 4
FLL
Fort Lauderdale - Hollywood Intl.
ORH
Worcester Regional
$253 Roundtrip, found 1 day ago
$253
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Oct 2 from Fort Lauderdale - Hollywood Intl. to Worcester Regional, returning Sun, Oct 4, priced at $253 found 1 day ago
OriginDestinationTravel DatesFlights From*
MCOLondonderrySeptember 16 to September 26$146
LGAWorcesterAugust 3 to August 4$181
DCALondonderryAugust 4 to August 6$216
ATLLondonderrySeptember 16 to September 23$252
MCOWorcesterSeptember 11 to September 13$253
TPALondonderryAugust 23 to August 29$263
RDUWorcesterAugust 3 to August 4$268
CLTLondonderryOctober 17 to October 19$282
ATLWorcesterSeptember 5 to September 12$307
TPAWorcesterAugust 17 to September 2$309
DCAWorcesterAugust 28 to August 31$315
CLTWorcesterOctober 14 to October 17$398
PHLLondonderrySeptember 18 to September 20$451
LGALondonderryAugust 26 to August 30$452
PHLWorcesterAugust 28 to September 2$655
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RDULondonderryJuly 19 to July 23$309
MCOLondonderryJuly 18 to July 22$359
DCALondonderryJuly 18 to July 20$404
MCOWorcesterJuly 18 to August 1$436
CLTLondonderryJuly 18 to July 25$472
DCAWorcesterJuly 18 to July 19$569
TPAWorcesterJuly 18 to August 1$746
*Prices include taxes and fees

Best Cheshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Centennial
4.0-star property

The Centennial

Sep 18 - Sep 21

3 night stay

Philadelphia (PHL) to Manchester (MHT)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $707, price is now $473 per person
$473
per person
found 1 day ago
Anchor at Tideline
3.0-star property

Anchor at Tideline

Sep 3 - Sep 7

4 night stay

Jacksonville (JAX) to Manchester (MHT)

JetBlue Airways • Coach

Manchester (MHT) to Jacksonville (JAX)

Southwest Airlines • Coach
Price was $875, price is now $676 per person
$676
per person
found 1 day ago
Latchis Hotel
2.5-star property

Latchis Hotel

Aug 24 - Aug 28

4 night stay

Greenville (GSP) to Springfield (VSF)

American Airlines • Non-stop • Coach

Springfield (VSF) to Greenville (GSP)

Delta • Non-stop • Coach
Price was $854, price is now $672 per person
$672
per person
found 7 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! (1,000 reviews)
"We had a great stay overall. The hotel was clean, well-maintained, and the staff was friendly, welcoming, and courteous throughout our visit. Breakfast was good, but the pancake station became backed up during the busy morning rush. Adding a second pancake machine would help reduce the wait and make ..."

Reviewed on Jul 14, 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! (1,001 reviews)
"Very nice experience, clean, good service, will recommend it"

Reviewed on Jul 16, 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! (1,012 reviews)
"Budget hotel, and I would stay again. My experience was thus: Pros: Cheap (cheapest room around) Quiet (no one bothered me) Cold (the air conditioning worked great; stayed cool in very hot summer days) Location (walking distance to a Target, a sporting goods store, a steakhouse etc. It's not a sketchy ..."

Reviewed on Jul 13, 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! (1,000 reviews)
"Friendly staff"

Reviewed on Jul 15, 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 $127 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 September. 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. $127 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 $127 and $746. 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.