Windsor Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp173.195 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Windsor
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is Rp1.478.230 per night from 30 Apr to 1 May
Rp1.478.230
Rp1.839.198 total
30 Apr - 1 May
includes taxes & fees
8.8/10 Excellent! (2,334 reviews)
Very nice
Reviewed on 12 Apr 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is Rp2.446.338 per night from 14 May to 15 May
Rp2.446.338
Rp2.732.560 total
14 May - 15 May
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Nice staff comfy bed nice views
Reviewed on 8 Apr 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is Rp1.409.468 per night from 26 Apr to 27 Apr
Rp1.409.468
Rp1.957.261 total
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (906 reviews)
Clean, hot shower. Great pressure
Reviewed on 14 Apr 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
