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 20 hours ago
$127
Roundtrip
found 20 hours 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 20 hours ago
Tue, Jan 26 - Sun, Jan 31
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$137 Roundtrip, found 22 hours ago
$137
Roundtrip
found 22 hours 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 22 hours ago
Tue, Feb 23 - Tue, Mar 2
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$142 Roundtrip, found 2 hours ago
$142
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Feb 23 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Tue, Mar 2, priced at $142 found 2 hours 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
Tue, Dec 8 - Sun, Dec 13
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Breeze Airways flight, departing Tue, Dec 8 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Dec 13, priced at $147 just found
Wed, Sep 30 - Sat, Oct 3
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$148 Roundtrip, found 6 days ago
$148
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Sep 30 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Oct 3, priced at $148 found 6 days ago
Thu, Aug 13 - Thu, Aug 20
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$181 Roundtrip, found 6 days ago
$181
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Aug 13 from Southwest Florida Intl. to Manchester-Boston Regional, returning Thu, Aug 20, priced at $181 found 6 days ago
Thu, Aug 13 - Thu, Aug 20
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$219 Roundtrip, found 6 days ago
$219
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 13 from Southwest Florida Intl. to Manchester-Boston Regional, returning Thu, Aug 20, priced at $219 found 6 days ago
OriginDestinationTravel DatesFlights From*
MCOLondonderrySeptember 16 to September 19$151
RDULondonderryAugust 30 to September 3$162
LGAWorcesterAugust 3 to August 4$181
DCALondonderryAugust 4 to August 6$216
MCOWorcesterSeptember 11 to September 13$253
TPALondonderryAugust 23 to August 29$263
RDUWorcesterAugust 24 to August 25$268
CLTLondonderrySeptember 22 to September 29$282
DCAWorcesterJuly 31 to August 2$300
TPAWorcesterAugust 17 to September 2$309
PHLWorcesterAugust 20 to August 23$357
CLTWorcesterOctober 14 to October 17$398
ATLWorcesterSeptember 4 to September 7$400
TTNLondonderryAugust 12 to August 15$446
LGALondonderryAugust 26 to August 30$452
*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
TPALondonderryJuly 17 to July 22$468
CLTLondonderryJuly 18 to July 25$472
TPAWorcesterJuly 17 to July 19$553
DCAWorcesterJuly 18 to July 19$591
ATLWorcesterJuly 17 to July 19$902
PHLWorcesterJuly 17 to July 18$1,325
*Prices include taxes and fees

Best Cheshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
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 20 hours ago
Cold Spring Plymouth Resort
3.5-star property

Cold Spring Plymouth Resort

Oct 8 - Oct 12

4 night stay

Houston (HOU) to Manchester (MHT)

JetBlue Airways • Non-stop • Coach

Manchester (MHT) to Houston (HOU)

Southwest Airlines • Non-stop • Coach
Price was $1,059, price is now $769 per person
$769
per person
found 1 day ago
The Lake Estate on Winnisquam
4.5-star property

The Lake Estate on Winnisquam

Aug 4 - Aug 8

4 night stay

Houston (HOU) to Manchester (MHT)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,672, price is now $1,247 per person
$1,247
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.
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! (1,000 reviews)
"The room, including the bathroom, was very clean. The shower was super clean. The breakfast was amazing! The lady who gets the food ready does a phenomenal job."

Reviewed on Jul 12, 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! (1,006 reviews)
"Garbage still in the trash cans, mini fridge had some kind of animal medication in it, microwave was dirty, huge pee stains on mattress, bathroom sink did not drain well"

Reviewed on Jul 10, 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 $1,325. 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.