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

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Windsor cottages

Exterior

1. Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 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 $315
CA $844 total
includes taxes & fees
Aug 3 - Aug 4
Terrific 3-bedroom cottage with AC in charming Cavendish
Exterior

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (13 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is CA $167
CA $299 total
includes taxes & fees
Aug 1 - Aug 2
Addie's Place: A Quiet and Quirky Guesthouse
House (2 Bedrooms) | Interior

3. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is CA $398
CA $626 total
includes taxes & fees
Aug 3 - Aug 4
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Family Cabin, 2 Bedrooms, Mountain View | View from room

4. 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
Aug 3 - Aug 4
Brook Road Cabin
House (5 Bedrooms) | Interior

5. 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 $1,667
CA $2,681 total
includes taxes & fees
Aug 1 - Aug 2
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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Top Windsor Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"We stayed here as the hotel for the event we were attending was booked. Paid same price and got breakfast, was a plus!"
nancy 1-night trip
Posted less than an hour ago
The Mountain Inn at Killington

Find out more about Windsor

Windsor Cottages information

Number of reviews
12
Accommodation
91 Cottages
Lowest Price
CA $299
Highest Price
CA $2,681

Frequently asked questions

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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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