Search and Rent Windsor Condos

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Next weekend
Jan 16 - Jan 18
In two weeks
Jan 23 - Jan 25
In one month
Feb 6 - Feb 8
In two months
Mar 6 - Mar 8

Our top choices for Windsor condo rentals

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,204 reviews)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Jan 12 - Jan 13
Total with taxes and fees
Vacation Village in the Berkshires
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (2 reviews)
"very nice and roomy! really enjoyed."
United States
Shack M.
$269 nightly
The price is $300
Jan 12 - Jan 13
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.2 out of 10, Good, (11 reviews)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
$303 nightly
The price is $338
Jan 12 - Jan 13
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"lovely place to stay"
United States
Nancy P.
$349 nightly
The price is $390
Feb 8 - Feb 9
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
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

The Williams Inn

The Williams Inn

10/10 Excellent
"General ambience is lovely."
Fiona 1-night trip
Posted 3 days ago
The Williams Inn

Find out more about Windsor

Windsor Condo Rentals information

Number of reviews
2,227
Accommodation
45 Condo Rentals
Lowest Price
$141
Highest Price
$390

Frequently asked questions

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We think that vacations shouldn't be complicated, so if you're in search of condos at the perfect price, Expedia has your back. Keep the budget under control and stay in something cheap and cheerful, or splurge on a high-end condo and pamper your loved ones. Our search filters make it simple to find a place in Windsor that fits your needs.
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