Search Condos Rentals in Windsor from CA $174

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Windsor condo rentals

Exterior

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,305 reviews)
"Great place in Williamstown. Near ski resort."
United States
Jason
The price is CA $143
CA $174 total
includes taxes & fees
Mar 17 - Mar 18
Vacation Village in the Berkshires
Outdoor dining

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)
"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.
The price is CA $188
CA $463 total
includes taxes & fees
Apr 1 - Apr 2
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
9.8 out of 10, Exceptional, (17 reviews)
"lovely place to stay"
United States
Nancy P.
The price is CA $307
CA $648 total
includes taxes & fees
Mar 17 - Mar 18
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.4 out of 10, Exceptional, (3 reviews)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is CA $188
CA $414 total
includes taxes & fees
Mar 17 - Mar 18
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Really helpful and nice staff, lovely and sophisticated decor/vibe, and great location. Loved the Le Labo bath products, too!"
Aki 1-night trip
Posted 4 hours ago
Berkshires Untold

Find out more about Windsor

Windsor Condo Rentals information

Number of reviews
2,321
Accommodation
45 Condo Rentals
Lowest Price
CA $174
Highest Price
CA $463

Frequently asked questions

Why book your condo in Windsor with Expedia?
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.
How can I find cheap condos in Windsor?
Expedia can help you track down cheap condos in Windsor. To find your perfect stay in a couple of quick clicks, use our handy filter tool to refine your search by amenities, star rating and budget.

Explore a world of travel with Expedia