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Cheshire

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Cheshire Flights as Low as $186

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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.

Just the right flight

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.

Frequently Asked Questions About flights to Cheshire

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 September, 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 15 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 $186, 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 $186 right now, why wait?

Can I fly to Cheshire right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Cheshire Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$186

Last Minute Hotel Deals in Cheshire

The Lenox Collection
The Lenox Collection
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is $125 per night from Jul 9 to Jul 10
$125
per night
Jul 9 - Jul 10
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (170 reviews)
"The propery is gorgeous. So charming. Staff was very friendly. Very nice room with awesome shower, super comfy bed, and quietly efficient air conditioner."

Reviewed on Jun 21, 2024

The Lenox Collection
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
The price is $169 per night from Jul 1 to Jul 2
$169
per night
Jul 1 - Jul 2
Stay at this 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 in our ...
8.4/10 Very Good! (931 reviews)
Nifty hotel in a great little town
"The room was clean and distinctive. Everything worked properly. The hotel is perfectly located for accessing anything in town by foot, including MassMOCA and various eateries."

Reviewed on Jun 16, 2024

Hotel Downstreet
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $150 per night from Jul 9 to Jul 10
$150
per night
Jul 9 - Jul 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! (272 reviews)
"Very pleasant place to stay rooms and nice and clean. Staff is very nice."

Reviewed on Jun 21, 2024

Life House Berkshires
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 $144 per night from Jul 10 to Jul 11
$144
per night
Jul 10 - Jul 11
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! (1,003 reviews)
"Employees were all super friendly, a very clean and pleasant property. There was nothing that I didn’t like about this place"

Reviewed on Jun 22, 2024

The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
The price is $199 per night from Jun 27 to Jun 28
$199
per night
Jun 27 - Jun 28
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
8.8/10 Excellent! (1,008 reviews)
"The hotel was great! The rooms were clean and well appointed."

Reviewed on Jun 21, 2024

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $180 per night from Jul 22 to Jul 23
$180
per night
Jul 22 - Jul 23
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the restaurant in our ...
8.8/10 Excellent! (905 reviews)
"Classic hotel but our room was far from main desk and fairly inconvenient. Room was in a separate annex"

Reviewed on Jun 23, 2024

The Red Lion Inn
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 $179 per night from Jun 27 to Jun 28
$179
per night
Jun 27 - Jun 28
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 pool and the clean ...
8.8/10 Excellent! (490 reviews)
Family get away!
"Everything is excellent just right! Went in a short trip with the grandchildren and everyone loves the accommodations! Lot's to do for all ages!"

Reviewed on Jun 25, 2024

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Quality Inn
Quality Inn
2.5 out of 5
170 Housatonic Street, Lee, MA
The price is $127 per night from Jul 9 to Jul 10
$127
per night
Jul 9 - Jul 10
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
8/10 Very Good! (926 reviews)
"Staff was courteous"

Reviewed on Jun 24, 2024

Quality Inn
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.