Windsor Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ₩234,741 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Find the Best Windsor Vacation Packages
Windsor Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is ₩130,720 per night from Nov 2 to Nov 3
₩130,720
₩161,647 total
Nov 2 - Nov 3
includes taxes & fees
8.6/10 Excellent! (2,049 reviews)
Check-in Needs Improvement
"Why have an on-line pre-check process if you have to wait in a long line when you arrive. Need to have separate line(s) for those who pre-check."
Reviewed on Oct 11, 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is ₩184,905 per night from Nov 12 to Nov 13
₩184,905
₩206,538 total
Nov 12 - Nov 13
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
Reviewed on Oct 9, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is ₩132,822 per night from Nov 2 to Nov 3
₩132,822
₩180,199 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (695 reviews)
"We stayed twice in the same week. The first room was great - no issues. The second stay (different room/different floor) seemed dated. Shower head was bad - so strong the tub filled. Moisture issues on the walls - walls peeling in bathroom, cracks in the sink around the bathroom sink drain. Crumbs ..."
Reviewed on Oct 12, 2025
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 package bookings compared to the price of the same components booked separately. Savings not available on all packages.
