A snow-covered river valley with a bridge and a town.

Search Chalets in Windsor from CA $622

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windsor chalets

A wooden deck with a hot tub, a table, and chairs.

1. Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
North Sherburne
8.2 out of 10, Very good, (14 reviews)
"We had a great time!"
United States
Matthew R.
The price is CA $210
CA $622 total
includes taxes & fees
Sep 28 - Sep 29
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
An outdoor deck with Adirondack chairs, a fire pit, and string lights against a backdrop of a forested landscape.

2. Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway

Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
Woodstock
The price is CA $436
CA $727 total
includes taxes & fees
Sep 17 - Sep 18
Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
A hot tub surrounded by snow-covered trees.

3. BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf

BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf
Killington
10.0 out of 10, Exceptional, (10 reviews)
"Great quite location near restaurants and 5 mins from the slopes. The kids loved the little arcade area and the hot tub was great for after skiing. Furniture was a little outdated but met our needs for a fun family vacation"
United States
Uyen B.
The price is CA $320
CA $754 total
includes taxes & fees
Sep 8 - Sep 9
BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf
A cabin with a gravel path leading to it, surrounded by trees and a wooden deck.

4. BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Great property - excellent hosts. Close to mountain and restaurants"
United States
Eric D.
The price is CA $562
CA $1,298 total
includes taxes & fees
Sep 7 - Sep 8
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
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

Hotel Coolidge

Hotel Coolidge

10/10 Excellent
"Surprisingly affordable, in the midst of downtown White River Jct., our stay in this historic hotel was pleasant and charming, the room clean and inviting, and the staff welcoming and helpful. Check in and check out were a breeze. Parking is still free for guests, and a breakfast voucher is available to use at the restaurant."
Tabatha 1-night trip
Posted 3 hours ago
Hotel Coolidge

Find out more about Windsor

Windsor Chalets information

Number of reviews
29
Accommodation
47 Chalets
Lowest Price
CA $622
Highest Price
CA $1,298

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