Cheshire Holiday Deals

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Cheshire Holiday Package Deals

Love getaways but hate details, paperwork and online forms? Let's make things a bit easier. At lastminute.com.au, we can combine all your hotel bookings, hire cars, airfares and amazing activities into a tidy little package. You'll save heaps of cash and have extra time for #Cheshire adventures!

With average savings of around , you might as well splurge a little on your lodgings (or at least plan an extra night out).

Take your pick from 400 airlines and 282,000 worldwide hotels. With so many options, you can craft a deal to suit your own individual style.

Think package deals can't get any better? Challenge accepted. With our Price Pledge, if you find a lower price on your hotel or package within 24 hours of booking online, we'll match it by refunding you the difference.Terms and conditions apply.

Holidays in Cheshire

As all travellers know — a life full of surprises and adventure is a life well-lived. So dig out your passport, pack your things and say hello to Cheshire!

If you journey 190 kilometres of Cheshire, you'll find yourself in the significant city of Montpelier.

You don't need to be stuck in a car all day to experience some nature. Just 8 kilometres out of Cheshire, Mount Greylock is an excellent place to get some fresh air. Even more tranquil surrounds await at Albany Visitors Center, 50 kilometres away.

Are you interested in the area's religious side? Stop by St Mary's of the Assumption Church.

Join the masses of excited fans rooting for the Tri-City ValleyCats at their home ground of Joseph L Bruno Stadium, 45 kilometres away in Albany. Fit in with the locals by getting into the team colours, red, grey and white.

Spend a leisurely day alternating between the frosty slopes and a cosy fire at Okemo Mountain Resort and Mount Snow. From newcomers to experts, there's something to please everyone at these winter paradises.

Want more things to see and do? Head to Adams, 8 kilometres north of Cheshire, for the Mass MoCA and the Topia Arts Center. Alternatively, New Ashford is 8 kilometres to the northwest, and it's here you'll discover Mount Greylock State Reservation Visitor Center and Jiminy Peak Mountain Resort.

Plan on going to Pittsfield? This place is just 15 kilometres to the southwest. If you're setting up base here, get a map and circle the Arrowhead Museum, Bousquet Ski Area and Canoe Meadows Wildlife Sanctuary. Also consider taking a peek at the Berkshire Athenaeum and the Berkshire Museum.

To truly experience a destination is to try the local food and drink, so prepare to chew, chomp, sip and slurp your way through The Berkshires. The only thing you need to bring with you is a hearty appetite!

Food here often includes cod and clams, two ingredients for which the region is famous for serving up.

Frappe is a dessert that sums up this place in just a single mouthful. Order up a serving and see how long it takes until you're back for more!

Held each year on the 4th of July, Independence Day holds a special place in the hearts of the locals. It offers a wonderful chance to discover the nation's past and have a little fun while you're at it!

When you're ready to take to the skies, give yourself plenty of time to head to Bradley International Airport (BDL). Sitting 80 kilometres to the southeast from the middle of Cheshire, this is the closest terminal.

Hotels in Cheshire

Planning on staying a couple of nights? You'll want to move quickly as there are only 3 Cheshire hotels on offer. So why wait any longer? Let lastminute.com.au help you today!

Choose to stay at any of our more popular accommodations, such as The Spring's Inn and The Weathervane Motel, and you'll be certain to bounce out of bed rejuvenated and refreshed each morning.

Top hotels for your Cheshire holiday

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 24 Apr to 25 Apr
AU$174
includes taxes & fees
24 Apr - 25 Apr
With a stay at Berkshires Untold in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
"Very nice"

Reviewed on 8 Apr. 2025

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
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 22 Apr to 23 Apr
AU$159
includes taxes & fees
22 Apr - 23 Apr
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
"Under renovation but didnt bother us.room was nice and clean and staff was accommodating. Breakfastbar is limited but satisfactory."

Reviewed on 7 Apr. 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 28 Apr to 29 Apr
AU$215
includes taxes & fees
28 Apr - 29 Apr
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood ...
"Condo built in 90's - good condition. Didn't know unit was two floors with spiral staircase - we are in our 60's so that wasn't great."

Reviewed on 8 Apr. 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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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.

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^Savings based on all package bookings made with Flight + Hotel on lastminute.com.au from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.