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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Windsor condo rentals

Pool

1. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
$344 nightly
The price is $385
Aug 9 - Aug 10
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

2. 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.6 out of 10, Good, (13 reviews)
"Great location, right on the mountain's property "
United States
J S.
$370 nightly
The price is $413
Sep 1 - Sep 2
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Very nice space with a full kitchen. You can definitely stay here for a week comfortably. Personally, I didn’t think the bed or the pillows were that comfortable but other than that, it was great."
Cindy 1-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Windsor

Windsor Condo Rentals information

Number of reviews
10,494
Accommodation
42 Condo Rentals
Lowest Price
$68
Highest Price
$239

Frequently asked questions

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