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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
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 AU$724
includes taxes & fees
2 Nov - 3 Nov
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
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, (19 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is AU$327
includes taxes & fees
22 Oct - 23 Oct
Addie's Place: A Quiet and Quirky Guesthouse
A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

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 AU$484
includes taxes & fees
22 Oct - 23 Oct
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A wooden deck with a table and chairs, surrounded by greenery and a wooden fence.

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 AU$408
includes taxes & fees
22 Oct - 23 Oct
Brook Road Cabin
A green wooden house with a sloped roof and a front porch.

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 AU$3,068
includes taxes & fees
24 Oct - 25 Oct
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Beautiful place that offers lots for guest to do. Room was beautiful with nice view and personal balcony with furniture! Only suggestions are our room was a king suite with lake deck and there was only one mirror to get ready with over the sink. This would be fine but sinks are small with no counter top space. So a full body mirror would be great with plugins near to get ready by. Had kayaks, fire pit, outdoor games, hiking trails around, sauna and hot tub, bar, and free breakfast."
sarah 1-night trip
Posted 9 hours ago
Mountain Meadows Lodge

Find out more about Windsor

Windsor Cottages information

Number of reviews
29
Accommodation
88 Cottages
Lowest Price
AU$327
Highest Price
AU$3,068

Frequently asked questions

What is there to do in Windsor near my cottage?
There are plenty of awesome things to put on your itinerary in Windsor. Drop by popular attractions like Mt Ascutney State Park, Harpoon Brewery and American Precision Museum. Arrowhead Recreation Area, Maple Lanes and Aidron Duckworth Art Museum also lure many visitors.

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