Windsor Holiday Deals

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Windsor Holiday Package Deals

At lastminute.com.au, we can bundle all of your hotel bookings, hire cars, airfares and amazing activities into a convenient package. So, why do this? You'll have more time for #Windsor adventures and you'll save tons of money!

With average savings of around , you may as well splurge a little on your lodgings (or at least get stuck into that minibar).

Our huge database has no less than 400 airlines and 282,000 worldwide hotels. Craft a package that's as unique as you are!

Keep in mind that we're willing to put our prices against any other site out there. And 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 Windsor

Cool! You've had your leave signed off. Now all you need to do is wave goodbye to your boss and book a ticket to Windsor — pronto!

From Windsor, head 200 kilometres north to reach the renowned city of Montpelier.

Break free on a journey to some nearby natural attractions. 17 kilometres out of Windsor, Mount Greylock is all yours to discover. Mount Tom, 45 kilometres away, is another pleasant place to kick your feet up.

Located 45 kilometres away, Mullins Center is a favourite for college basketball enthusiasts. Pack some maroon and white, and time your stay with a live game featuring the home team, the UMass Minutemen. You can also give your support to the second home team, the UMass Minutemen.

Whether you'd like to polish your turns or simply get back to base in one piece, The Berkshires has the slopes for you. Get your fill of outdoor fun at either Mount Snow or Ski Sundown.

You'll discover even more just down the road. Savoy, 9 kilometres to the north, is known for the Topia Arts Center and Susan B. Anthony Birthplace Museum. Alternatively, if Mount Greylock State Reservation Visitor Center and the Skyline Country Club are more appealing, head 10 kilometres northwest from Windsor to Cheshire.

You may get the urge to book a room in Charlemont for a while. This destination is 18 kilometres away and not too far from Hawley Bog Preserve, Berkshire East Ski Resort and Bissell Covered Bridge. Other nearby sights are the Hail to the Sunrise Statue and Charlemont Federated Church.

Tantalise your taste buds and fill your Instagram account with mouthwatering images by indulging in some of the region's most delicious food and drink offerings. Just don't forget to hashtag 'yum'!

Searching for some insight into the regional cuisine? We recommend tasting cod and clams, two staples which make up a range of dishes here.

You might be eating yourself into elastic-waisted slacks, but frappe is worth every calorie. This beloved dessert will make your taste buds tingle at the sight of it.

What better way to learn about a place than by joining in on a day of national celebration? There'll be many festivities occurring for Independence Day on the 4th of July.

Bradley International Airport (BDL), the closest airport, is some 70 kilometres to the southeast from the centre of Windsor. Plan a route, pack up your bags and set an alarm clock — and be sure not to hit the snooze button too many times!

Top hotels for your Windsor holiday

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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$123 per night from 19 Aug to 20 Aug
AU$123
19 Aug - 20 Aug
includes taxes & fees
Located in Pittsfield, FairBridge Inn Express is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Berkshire Athenaeum.
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on 2 Aug. 2025

FairBridge Inn Express
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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.

^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.