Search Condo Rentals in Windsor

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare Condo Rentals in Windsor with updated reviews, rates, and availability.

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Windsor

Riverfront Sanctuary

10.0 out of 10, Exceptional, (3)
"This was a perfect location and setting for our family stay to attend our nephews wedding. The home has so much character with antique furnishings and a beautiful country setting overlooking the river. The hosts were very accommodating, responsive and a pleasure to deal with. "
Riverfront Sanctuary

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (135)
"My mid-October stay at Little Thumb was everything I hoped for and more: plenty of peace and quiet, an immaculate and comfortable place to stay, and beautiful surroundings in which to birdwatch from the dock, read, and take long walks. I especially enjoyed the well-stocked kitchen, comfy queen bed, and big gas heating stove in the living room that kept me toasty, even temps dipped into the 40s. And Natalie certainly deserves her rating as a top host!"
Updated lake cottage right on Damariscotta Lake.

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.8 out of 10, Exceptional, (19)
"We had an awesome time playing in the snow in the backyard and enjoying the relaxing hot tub. The house accommodated our large family and the host was very responsive and came quickly when we needed help. Will definitely come back "
Spacious Country Home w/ Hot Tub, near Colby/Thomas
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.

Frequently asked questions

Why book your condo in Windsor with Expedia?
We think that vacations should be stress-free, so if you’re on the lookout for condos at a nice price, Expedia has your back. Keep the budget in check and check in to something small and affordable, or book a 5-star condo and really spoil your crew. Our search filters make it simple to find a stay in Windsor that checks your boxes.
How can I find cheap condos in Windsor?
With Expedia’s handy filter tool, comparing cheap condos in Windsor is a breeze. To view properties that are very pocket friendly, tailor your search results by star rating, budget and amenities.