Photo by William E Berry Jr.

Search Windsor Villa Rentals

    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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Windsor Villas

Pinnacle D02, Lovely 2 bedroom, 2 bath unit with shuttle to the slopes everyday of the week. The outdoor pool, hot tub and tennis courts are open during summer only.
Pool
Pinnacle D02, Lovely 2 bedroom, 2 bath unit with shuttle to the slopes everyday of the week. The outdoor pool, hot tub and tennis courts are open during summer only.
10.0 out of 10, Exceptional, (2)
"great room. clean. there is everything you need for a comfortable stay. definitely 5 stars. We'll be back."
Pinnacle D02, Lovely 2 bedroom, 2 bath unit with shuttle to the slopes everyday of the week. The outdoor pool, hot tub and tennis courts are open during summer only.
Private wing of the Largest Colonial Revival Mansion in the US
Exterior
Private wing of the Largest Colonial Revival Mansion in the US
Private wing of the Largest Colonial Revival Mansion in the US
Hakuna Matata - GetAway
Townhome, 3 Bedrooms, Mountain View, Mountainside | Private kitchen
Hakuna Matata - GetAway
3.5 star property
6.0 out of 10, (1)
Hakuna Matata - GetAway
Don't see what you're looking for?
See all available properties in Windsor
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.

Other property types in Windsor

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (32)
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (177)
"This property was beautiful and literally had everything we needed to cook family meals including spices and all necessary pots/pans. I was impressed by how much this hike had available form our convenience. My only issue is that the home is advertised as a 2 bedroom but it is a loft space with 3 beds and no doors. We were not expecting this but made it work. Other than that this place is a slice of heaven!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Beautifully renovated with fireplace and coffee bar
Smart TV, fireplace, books
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (61)
"This is a sweet convo with lovely views from all windows. There is a porch off the kitchen where you can sit and hear birds. Fragrant lilac as you come up the stairs to the door. Wanda was very easy to work with, friendly and available. We thoroughly enjoyed the coffee bar, and in all, had a wonderful stay."
Beautifully renovated with fireplace and coffee bar
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.

Windsor Villas information

Number of reviews
3
Accommodation
3 Villas
Lowest Price
Highest Price

Recent Reviews in Windsor
Expedia verified reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

5/5 Excellent
"Hot tub was so niceeee and the rooms were cute no microwave though "
A verified traveller stayed at Pointe at Castle Hill Resort
Posted 13 hours ago
Pointe at Castle Hill Resort