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

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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 £439
includes taxes & fees
4 Aug - 5 Aug
Terrific 3-bedroom cottage with AC in charming Cavendish
House (2 Bedrooms) | Interior

2. 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 £332
includes taxes & fees
4 Aug - 5 Aug
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Family Cabin, 2 Bedrooms, Mountain View | View from room

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 £222
includes taxes & fees
5 Aug - 6 Aug
Brook Road Cabin
Exterior

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (14 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is £152
includes taxes & fees
4 Aug - 5 Aug
Addie's Place: A Quiet and Quirky Guesthouse
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 £1,420
includes taxes & fees
4 Aug - 5 Aug
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

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

8/10 Good
"Pros Clean room, lobby and elevator. Nice and comfortable lobby chairs and tables. The king bed was super comfortable to sleep on. Cons Seems like the breakfast staff member are over work. No smile they seem frustrated. The pool is small around 4ft depth? I didn't bother to go its more appealing for children than to adults. Shower head kept leaking which I reported but it seem like its a common thing since nothing was done about it."
Ricardo 1-night trip
Posted 1 hour ago
Hilton Garden Inn Hanover Lebanon

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Windsor Cottages information

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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?
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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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