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

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  • Upfront pricing

    We are not like the others - we include taxes and fees

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.
$543 nightly
The price is $608
Aug 3 - Aug 4
Total with taxes and fees
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.
$193 nightly
The price is $218
Aug 1 - Aug 2
Total with taxes and fees
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
$406 nightly
The price is $447
Aug 3 - Aug 4
Total with taxes and fees
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
$291 nightly
The price is $315
Aug 11 - Aug 12
Total with taxes and fees
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
$1,740 nightly
The price is $1,915
Aug 1 - Aug 2
Total with taxes and fees
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
"For a a hotel in the middle of nowhere, they get everything as right as they can… more than adequate gym, pool (my 14 yr old desperately needed to burn off some energy at 8pm at night!) The rooms are spacious for what they are, the bathrooms a new, clean, modern (always need more towels. A room for 4 can’t function on 3 towels - that’s ridiculous) … the pillows kind of sucked … these small hotels are dying for housekeepers but the front desk staff makes a terrific and much appreciated effort. We stay at this hotel every summer when we drop off our son for camp… it’s always a relief at how nice it is for where it is and the price point"
Maureen 1-night trip
Posted 5 hours ago
Hilton Garden Inn Hanover Lebanon

Find out more about Windsor

Windsor Cottages information

Number of reviews
12
Accommodation
90 Cottages
Lowest Price
$218
Highest Price
$1,915

Frequently asked questions

Why book your cottage in Windsor with Expedia?
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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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