Find vacation rentals that suit your style
Cabins
Aparthotels
Our top choices for Windsor cottages
1. Addie's Place: A Quiet and Quirky Guesthouse
Addie's Place: A Quiet and Quirky GuesthouseHartford
9.6 out of 10, Exceptional, (23 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
Victor R.
$194 nightly
The price is $219
Nov 15 - Nov 16
Total with taxes and fees
2. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6Cavendish
10.0 out of 10, Exceptional, (4 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
Mark G.
$516 nightly
The price is $578
Nov 14 - Nov 15
Total with taxes and fees
3. Brook Road Cabin
Brook Road CabinGoshen
7.4 out of 10, Good, (10 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
Jill
$296 nightly
The price is $321
Nov 15 - Nov 16
Total with taxes and fees
4. Game Room, Fire Pit & Views! Spacious Ludlow Home
Game Room, Fire Pit & Views! Spacious Ludlow HomeLudlow
$719 nightly
The price is $791
Nov 15 - Nov 16
Total with taxes and fees
5. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Luxe Mountain Home w/ Chefs Kitchen & Okemo ViewsLudlow
$1,955 nightly
The price is $2,151
Nov 14 - Nov 15
Total with taxes and fees
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.
Learn more about Windsor
Step back in time at the American Precision Museum, where industrial history comes alive through fascinating exhibits. Afterward, savor craft brews at Harpoon Brewery or hike the scenic trails of Mt Ascutney State Park for breathtaking views.
