Windsor Holidays
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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 2.616.242 ₫ per night from 20 Oct to 21 Oct
2.616.242 ₫
3.211.983 ₫ total
20 Oct - 21 Oct
includes taxes & fees
8.6/10 Excellent! (2,018 reviews)
"Clean, spacious, well designed room with everything needed gir a great stay …. And so much more. The balcony was a great place to sit, gave coffee etc. can’t say enough about the beautiful grounds and amenities like indoor and outdoor pool areas, etc! Enjoyed staying at Vacation Village in the Berkshire ..."
Reviewed on 24 Sept 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is 2.842.349 ₫ per night from 19 Oct to 20 Oct
2.842.349 ₫
3.764.746 ₫ total
19 Oct - 20 Oct
includes taxes & fees
8.8/10 Excellent! (656 reviews)
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."
Reviewed on 25 Sept 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is 3.421.829 ₫ per night from 2 Oct to 3 Oct
3.421.829 ₫
4.190.768 ₫ total
2 Oct - 3 Oct
includes taxes & fees
9/10 Wonderful! (738 reviews)
"The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area ..."
Reviewed on 22 Sept 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.
