Compare Windsor Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Windsor

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.

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.

Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Private wing of the Largest Colonial Revival Mansion in the US

Private wing of the Largest Colonial Revival Mansion in the US

This villa is a smoke-free villa.
Air conditioning
Hakuna Matata - GetAway

Hakuna Matata - GetAway

3.5 out of 5
This villa features free WiFi in public areas and a picnic area. There's free parking if you drive. This smoke-free villa also has barbecue grills.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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.

Hotel Options in Windsor

    Fat Sheep Farm & Cabins

    Fat Sheep Farm & Cabins

    122 Best Rd, Windsor, VT
    The price is $222 per night from May 4 to May 5
    $222
    includes taxes & fees
    $204 per night
    May 4 - May 5
    9.6/10 Exceptional! (9 reviews)
    Killington Mountain Lodge, Tapestry Collection by Hilton

    Killington Mountain Lodge, Tapestry Collection by Hilton

    2617 Killington Rd, Killington, VT
    The price is $134 per night from May 8 to May 9
    $134
    includes taxes & fees
    $122 per night
    May 8 - May 9
    7.2/10 Good! (1,002 reviews)
    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd, Quechee, VT
    The price is $132 per night from May 5 to May 6
    $132
    includes taxes & fees
    $120 per night
    May 5 - May 6
    9/10 Wonderful! (1,007 reviews)

Luxury Villas

Book luxury villas in Windsor
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Windsor. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Windsor, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Windsor
You won’t have a problem finding your own space in Windsor. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Windsor on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Windsor rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Windsor Villas essential information

Accommodation
3 Villas
Lowest Price
$132
Highest Price
$222
Popular accommodation
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, Hakuna Matata - GetAway

Villas in Windsor

Most Popular

More Places To Stay in Windsor