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

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Windsor cottages

Exterior

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 €519
includes taxes & fees
26 Jul - 27 Jul
Terrific 3-bedroom cottage with AC in charming Cavendish
House (2 Bedrooms) | Interior

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 €391
includes taxes & fees
21 Jul - 22 Jul
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Exterior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (12 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is €230
includes taxes & fees
11 Aug - 12 Aug
Addie's Place: A Quiet and Quirky Guesthouse
Family Cabin, 2 Bedrooms, Mountain View | View from room

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 €262
includes taxes & fees
21 Jul - 22 Jul
Brook Road Cabin
House (5 Bedrooms) | Interior

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is €1,617
includes taxes & fees
22 Jul - 23 Jul
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

10/10 Excellent
"We had an appointment at Dartmouth and staying at the hotel was convenient and enjoyable."
Claudette 1-night trip
Posted 8 hours ago
Hilton Garden Inn Hanover Lebanon

Find out more about Windsor

Windsor Cottages information

Number of reviews
24
Accommodation
91 Cottages
Lowest Price
€230
Highest Price
€1,617

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.