Search Windsor Cottage Rentals from CA $209

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Windsor cottages

A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

1. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Cavendish
10.0 out of 10, Exceptional, (3 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is CA $227
CA $700 total
includes taxes & fees
Nov 9 - Nov 10
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
A white house with a red roof and a hammock in the yard.

2. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (21 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is CA $210
CA $341 total
includes taxes & fees
Dec 7 - Dec 8
Addie's Place: A Quiet and Quirky Guesthouse
A wooden deck with a table and chairs, surrounded by greenery and a wooden fence.

3. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
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. 😊"
United States
Jill
The price is CA $257
CA $419 total
includes taxes & fees
Nov 16 - Nov 17
Brook Road Cabin
A green wooden house with a sloped roof and a front porch.

4. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is CA $1,920
CA $3,005 total
includes taxes & fees
Nov 13 - Nov 14
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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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Learn more about Windsor

Step back in time at the American Precision Museum, where industrial history comes alive through fascinating exhibits. Afterward, savour craft brews at Harpoon Brewery or hike the scenic trails of Mt Ascutney State Park for breathtaking views.

See all hotels in Windsor
A covered bridge over a river with lush greenery and a clear sky.

Frequently Asked Questions

Why book your cottage in Windsor with Expedia?

Expedia has some terrific cottages in Windsor, so start packing your bags for an unforgettable stay on nature's doorstep. If you need to stick to a budget, choose how much you'd like to spend and the preferred star rating of your property. Or, try out our filters to search for cottages with a hot tub or free WiFi. We'll help you find the right place whatever your bank balance or plans.

How can I find cheap cottages in Windsor?

With Expedia's filter tool, comparing cheap cottages in Windsor couldn't be easier. To discover stays that'll make your wallet smile, narrow your search by budget, amenities and star rating.

What is there to do in Windsor near my cottage?

Once you've unpacked your bags, get out and discover the wonderful things Windsor has to offer. American Precision Museum is a popular attraction to add to your travel itinerary.

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