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

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$172 per night from 10 Mar to 11 Mar
AU$172
includes taxes & fees
10 Mar - 11 Mar
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
"This is not your standard chain hotel. Although the overall architecture is 1970s motel style, the color choices, furnishings, and materials used in upgrading have produced a very sophisticated, upscale ambience. Life House Berkshire is promoted as a writer’s retreat. The lobby/bar appears to be ..."

Reviewed on 3 Mar. 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$142 per night from 16 Mar to 17 Mar
AU$142
includes taxes & fees
16 Mar - 17 Mar
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 ...
"This was a very nice little getaway from everyday life. The room was nice and roomy and we loved the fireplace."

Reviewed on 3 Mar. 2025

The Yankee, Trademark Collection by Wyndham
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$205 per night from 12 Mar to 13 Mar
AU$205
includes taxes & fees
12 Mar - 13 Mar
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 ...
"Customer Service Above And Beyond"

Reviewed on 5 Mar. 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.

^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.