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$173 per night from 19 Feb to 20 Feb
AU$173
includes taxes & fees
19 Feb - 20 Feb
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
"Love the value of this place! Cute rooms, amazing bar, and great location!"

Reviewed on 5 Feb. 2025

Life House Berkshires
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
The price is AU$210 per night from 20 Feb to 21 Feb
AU$210
includes taxes & fees
20 Feb - 21 Feb
A stay at Hotel Downstreet, Ascend Hotel Collection places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot ...
"The hotel was in a very walkable community. I enjoyed the galleries in the lobby and the art museum nearby."

Reviewed on 29 Jan. 2025

Hotel Downstreet
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$279 per night from 9 Feb to 10 Feb
AU$279
includes taxes & fees
9 Feb - 10 Feb
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 ...
"Great place"

Reviewed on 27 Jan. 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.