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Our top choices for Windsor condo rentals

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)
$283 nightly
The price is $320
Jan 11 - Jan 12, 2026
Total with taxes and fees

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski ResortCavendish
10.0 out of 10, Exceptional, (19)
$481 nightly
The price is $539
Jan 4 - Jan 5, 2026
Total with taxes and fees

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
2nd-floor downtown Ludlow studio condo with kitchenette, streamingLudlow
8.6 out of 10, Excellent, (4)
$268 nightly
The price is $303
Jan 5 - Jan 6, 2026
Total with taxes and fees

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFiClock Tower Base Area
8.6 out of 10, Excellent, (14)
$300 nightly
The price is $339
Jan 4 - Jan 5, 2026
Total with taxes and fees

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle RouteLudlow
10.0 out of 10, Exceptional, (102)
$324 nightly
The price is $354
Jan 12 - Jan 13, 2026
Total with taxes and fees

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Ski-In/Out condo with patio, mountain views, washer/dryer, & cableClock Tower Base Area
9.2 out of 10, Wonderful, (26)
$302 nightly
The price is $341
Jan 8 - Jan 9, 2026
Total with taxes and fees

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Condo with Seasonal Pool & Tennis Courts - Walk to Ski TrailsLudlow
7.6 out of 10, Good, (53)
$338 nightly
The price is $382
Jan 12 - Jan 13, 2026
Total with taxes and fees

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Condo in the heart of town near skiing - less than a mile to Okemo MountainLudlow
9.0 out of 10, Wonderful, (14)
$321 nightly
The price is $363
Jan 12 - Jan 13, 2026
Total with taxes and fees
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

Hideaway Inn Mt.Sunapee
10/10 Excellent
Find out more about Windsor
Windsor Condo Rentals information
Number of reviews | 340 |
|---|---|
Accommodation | 948 Condo Rentals |
Lowest Price | $303 |
Highest Price | $736 |
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