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Cheshire

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Cheshire Flights as Low as $158

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Sat, Mar 1 - Tue, Mar 4
MCO
Orlando Intl.
ALB
Albany Intl.
$158 Roundtrip, found 17 hours ago
$158
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Mar 1 from Orlando Intl. to Albany Intl., returning Tue, Mar 4, priced at $158 found 17 hours ago
American Airlines
Sat, Mar 1 - Tue, Mar 4
MCO
Orlando Intl.
ALB
Albany Intl.
$159 Roundtrip, found 17 hours ago
$159
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Mar 1 from Orlando Intl. to Albany Intl., returning Tue, Mar 4, priced at $159 found 17 hours ago
Delta
Thu, Mar 20 - Wed, Mar 26
MCO
Orlando Intl.
ALB
Albany Intl.
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Mar 20 from Orlando Intl. to Albany Intl., returning Wed, Mar 26, priced at $179 found 6 days ago
JetBlue Airways
Fri, Feb 28 - Sat, Mar 1
MCO
Orlando Intl.
ALB
Albany Intl.
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Feb 28 from Orlando Intl. to Albany Intl., returning Sat, Mar 1, priced at $183 found 1 day ago
Delta
Sat, Mar 1 - Tue, Mar 4
MCO
Orlando Intl.
ALB
Albany Intl.
$187 Roundtrip, found 17 hours ago
$187
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, Mar 1 from Orlando Intl. to Albany Intl., returning Tue, Mar 4, priced at $187 found 17 hours ago
JetBlue Airways
Thu, Mar 20 - Wed, Mar 26
MCO
Orlando Intl.
ALB
Albany Intl.
$187 Roundtrip, found 6 days ago
$187
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Mar 20 from Orlando Intl. to Albany Intl., returning Wed, Mar 26, priced at $187 found 6 days ago
United
Thu, Mar 20 - Wed, Mar 26
MCO
Orlando Intl.
ALB
Albany Intl.
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select United flight, departing Thu, Mar 20 from Orlando Intl. to Albany Intl., returning Wed, Mar 26, priced at $197 found 6 days ago
Delta
Thu, Mar 20 - Wed, Mar 26
MCO
Orlando Intl.
ALB
Albany Intl.
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Mar 20 from Orlando Intl. to Albany Intl., returning Wed, Mar 26, priced at $197 found 6 days ago
United
Thu, Mar 20 - Wed, Mar 26
MCO
Orlando Intl.
ALB
Albany Intl.
$202 Roundtrip, found 6 days ago
$202
Roundtrip
found 6 days ago
Select United flight, departing Thu, Mar 20 from Orlando Intl. to Albany Intl., returning Wed, Mar 26, priced at $202 found 6 days ago
JetBlue Airways
Sat, Mar 1 - Fri, Mar 7
MCO
Orlando Intl.
ALB
Albany Intl.
$207 Roundtrip, found 17 hours ago
$207
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Sat, Mar 1 from Orlando Intl. to Albany Intl., returning Fri, Mar 7, priced at $207 found 17 hours ago
American Airlines
Sat, Mar 1 - Tue, Mar 4
MCO
Orlando Intl.
ALB
Albany Intl.
$212 Roundtrip, found 17 hours ago
$212
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Mar 1 from Orlando Intl. to Albany Intl., returning Tue, Mar 4, priced at $212 found 17 hours ago
American Airlines
Wed, May 21 - Fri, May 30
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$252 Roundtrip, found 16 hours ago
$252
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Wed, May 21 from Charlotte-Douglas Intl. to Albany Intl., returning Fri, May 30, priced at $252 found 16 hours ago
American Airlines
Tue, Apr 29 - Tue, Apr 29
DTW
Detroit Metropolitan Wayne County
ALB
Albany Intl.
$278 Roundtrip, found 5 days ago
$278
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Apr 29 from Detroit Metropolitan Wayne County to Albany Intl., returning Tue, Apr 29, priced at $278 found 5 days ago
JetBlue Airways
Tue, May 20 - Wed, May 28
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$304 Roundtrip, found 5 days ago
$304
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, May 20 from Raleigh - Durham Intl. to Albany Intl., returning Wed, May 28, priced at $304 found 5 days ago
Delta
Tue, Jun 17 - Wed, Jun 25
AUS
Austin-Bergstrom Intl.
ALB
Albany Intl.
$357 Roundtrip, found 3 days ago
$357
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 17 from Austin-Bergstrom Intl. to Albany Intl., returning Wed, Jun 25, priced at $357 found 3 days ago
American Airlines
Mon, Mar 3 - Mon, Mar 3
JAX
Jacksonville Intl.
ALB
Albany Intl.
$641 Roundtrip, found 1 day ago
$641
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Mar 3 from Jacksonville Intl. to Albany Intl., returning Mon, Mar 3, priced at $641 found 1 day ago

Cheap Flights to Cheshire

Fall in love at first flight with your vacation to Cheshire by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Cheshire on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Cheshire, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Cheshire

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Cheshire with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the ALB airport.

What is the cheapest month to fly to Cheshire?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Cheshire are in March, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Cheshire?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Cheshire.

What airport is best to fly into Cheshire?

When you’re planning your trip to Cheshire, convenience is the name of the game. Luckily, Cheshire Pittsfield Municipal Airport is nearby so you can deplane and get going on checking off everything on your Cheshire must-do list.

How much are flights to Cheshire?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Cheshire on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $158, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Cheshire?

The trick to saving a stack of cash on your flight to Cheshire? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $158 right now, why wait?

Cheshire Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$157

Last Minute Hotel Deals in Cheshire

Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
The price is $132 per night from Mar 9 to Mar 10
$132
includes taxes & fees
Mar 9 - Mar 10
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,002 reviews)
Highly recommend
"Excellent service, convenient location, clean property"

Reviewed on Feb 18, 2025

Hotel Downstreet
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is $137 per night from Mar 9 to Mar 10
$137
includes taxes & fees
Mar 9 - Mar 10
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,762 reviews)
"Super clean and spacious. Rooms have everything you need for a long stay."

Reviewed on Feb 19, 2025

Vacation Village in the Berkshires
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $108 per night from Mar 9 to Mar 10
$108
includes taxes & fees
Mar 9 - Mar 10
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (503 reviews)
Looks nice but is eh
"Life House Berkshires looks great, but no one actually works there. Or at least that's how it seemed during our stay. I never got the welcome text they said I would get to be able to communicate with staff. I called the 800 number once to try to get someone and couldn't get a person. I finally did ..."

Reviewed on Feb 19, 2025

Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is $147 per night from Feb 24 to Feb 25
$147
includes taxes & fees
Feb 24 - Feb 25
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (595 reviews)
Greatness
"It was a great little getaway from the city, service was great and helpful nothing to complain about this spot"

Reviewed on Feb 10, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is $200 per night from Feb 24 to Feb 25
$200
includes taxes & fees
Feb 24 - Feb 25
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (415 reviews)
"Amazing place to stay and eat"

Reviewed on Feb 21, 2025

The Williams Inn
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $211 per night from Feb 24 to Feb 25
$211
includes taxes & fees
Feb 24 - Feb 25
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,003 reviews)
"Love the history and ambiance. Service excellent. Restaurant dinner just fair. Clean rooms. Guests should not have to pay for music in the bar. Parking good. Very quiet."

Reviewed on Feb 22, 2025

The Red Lion Inn
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $89 per night from Mar 2 to Mar 3
$89
includes taxes & fees
Mar 2 - Mar 3
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,000 reviews)
"Staff was super nice, the rooms were really nice and clean."

Reviewed on Feb 17, 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
The price is $116 per night from Feb 28 to Mar 1
$116
includes taxes & fees
Feb 28 - Mar 1
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (738 reviews)
Dated but trying
"Great for the money. Unfortunately the jacuzzi was non-functional which was the one thing I was looking forward to after a ski day. Hotel staff was amazing."

Reviewed on Feb 17, 2025

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
See all 947 properties in Cheshire
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.