Flights To Cheshire County - Cheap Flights Starting at CA $93

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Cheshire County's top cities

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

Keene

Flights
Keene

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, Nov 4 - Sat, Nov 14
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $219 Roundtrip, found 2 days ago
CA $219
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Nov 4 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at CA $219 found 2 days ago
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $237 Roundtrip, found 12 hours ago
CA $237
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Sat, Dec 5 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Dec 12, priced at CA $237 found 12 hours ago
Sat, Sep 12 - Sat, Sep 19
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $256 Roundtrip, found 2 days ago
CA $256
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Sep 12 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Sep 19, priced at CA $256 found 2 days ago
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $258 Roundtrip, found 1 hour ago
CA $258
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Dec 5 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Dec 12, priced at CA $258 found 1 hour ago
Sat, Nov 7 - Wed, Nov 11
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
CA $289 Roundtrip, found 14 hours ago
CA $289
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Southwest Florida Intl. to Manchester-Boston Regional, returning Wed, Nov 11, priced at CA $289 found 14 hours ago
Wed, Nov 4 - Sat, Nov 14
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $319 Roundtrip, found 2 days ago
CA $319
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at CA $319 found 2 days ago
Wed, Nov 4 - Sat, Nov 14
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $319 Roundtrip, found 2 days ago
CA $319
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Nov 4 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at CA $319 found 2 days ago
Wed, Nov 4 - Sat, Nov 14
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $383 Roundtrip, found 2 days ago
CA $383
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at CA $383 found 2 days ago
OriginDestinationTravel datesFlights from*
MCOLondonderryNovember 4 to November 14CA $219
TPALondonderryNovember 12 to November 16CA $382
ATLWorcesterNovember 6 to November 8CA $429
RDULondonderrySeptember 10 to September 13CA $482
MCOWorcesterOctober 14 to October 18CA $530
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Exeter Inn
3.5-star property

Exeter Inn

Sep 11 - Sep 13

2 night stay

Toronto (YTZ) to Manchester (MHT)

Porter Airlines • Roundtrip • Coach
Price was CA $798, price is now CA $708 per person
CA $708
per person
found 13 hours ago
Cold Spring Plymouth Resort
3.5-star property

Cold Spring Plymouth Resort

Oct 9 - Oct 13

4 night stay

Detroit (DTT) to Manchester (MHT)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,526, price is now CA $1,259 per person
CA $1,259
per person
found 1 day ago
Latchis Hotel
2.5-star property

Latchis Hotel

Sep 4 - Sep 6

2 night stay

Toronto (YYZ) to Springfield (VSF)

WestJet • Non-stop roundtrip • Coach
Price was CA $1,352, price is now CA $1,208 per person
CA $1,208
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Toronto to Cheshire County
View all trips

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! (1,012 reviews)
"The staff was great, really kind and accommodating. The hotel was clean but not sparkling. It wasn’t dirty. It is definitely an older hotel that could use a makeover but it was reasonably priced safe and clean. I would stay here again if I was looking for an affordable clean option."

Reviewed on Aug 23, 2026

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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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! (680 reviews)
"The Riverside is a lovely place to stay when in the Brattleboro VT area. The rooms are spacious and exceptionally clean. View of the river makes for a nice setting. The hotel is very quiet. Staff are helpful and welcoming."

Reviewed on Aug 23, 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 CA $219 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 November. 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. CA $219 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 CA $219 and CA $530. 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.