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Windsor Holiday Rentals
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Our top choices for Windsor holiday rentals

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern TrailKillington
9.0 out of 10, Wonderful, (53)
The price is HK$1,726
HK$2,316 total
includes taxes & fees
15 Dec - 16 Dec

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy AccessKillington
The price is HK$1,230
HK$3,096 total
includes taxes & fees
5 Jan - 6 Jan 2026

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Ski-in/out mountainside condo close to everything with full kitchen - tranquilClock Tower Base Area
9.0 out of 10, Wonderful, (74)
The price is HK$654
HK$2,239 total
includes taxes & fees
16 Dec - 17 Dec

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to SkiingAndover
9.0 out of 10, Wonderful, (29)

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVEKillington
9.6 out of 10, Exceptional, (92)

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Cozy studio with balcony, full kitchen, and free WiFi - walk to liftsKillington
8.2 out of 10, Very good, (38)

The Cabin that brings people together
The Cabin that brings people togetherBridgewater
9.6 out of 10, Exceptional, (82)
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.
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Top Windsor Hotel Reviews

Hilton Garden Inn Hanover Lebanon
10/10 Excellent
Find out more about Windsor
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