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

Harbour House Inn

Harbour House Inn

3.5 out of 5
725 North State Road, Cheshire, MA
The price is AU$386 per night from 13 Aug to 14 Aug
AU$386
13 Aug - 14 Aug
includes taxes & fees
Located in Cheshire, Harbour House Inn is in the mountains, a 3-minute drive from St Mary's of the Assumption Church and 6 minutes from Adams Theater.
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!!"

Reviewed on 4 Jul. 2025

Harbour House Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
"Great price for area with clean and spacious suites. Would be perfect if offered on site breakfast."

Reviewed on 3 Aug. 2025

Berkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 27 Aug to 28 Aug
AU$175
27 Aug - 28 Aug
includes taxes & fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient"

Reviewed on 4 Aug. 2025

Vacation Village in the Berkshires
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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.