What types of vacation rentals are available in Windsor?

There are loads of different property types that you can make your vacation home in Windsor. You’ll find cabins, cottages and villas.

Are there any pet-friendly vacation rentals in Windsor?

There are a number of dog and pet-friendly Windsor vacation rentals, with around 38% allowing you to bring your pet along with you.

How can I find vacation rentals near me in Windsor?

Take a look at our vacation rentals map to find the best vacation rental homes near you.

Windsor Vacation Rentals from $222/night

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Best Windsor vacation rentals

Fat Sheep Farm & Cabins

Windsor, VT

10Wonderful(2)

Parking

Free Wi-Fi

Pet friendly

$222+

Check availability

Meriden Village of Plainfield Home with Backyard

Windsor, VT

7.3Good(3)

Free Wi-Fi

Pet friendly

$453+

Check availability

Enchanting farmhouse with a picture perfect view of Mt. Ascutney

Windsor, VT

Free Wi-Fi

$289+

Check availability

Exquisite Log Home with views near Woodstock, Vermont

Windsor, VT

$663+

Check availability

Cozy Historic Hilltop Cottage with Mount Ascutney View

Windsor, VT

Free Wi-Fi

$284+

Check availability

Beautiful Fall & Winter Views - Rustic Contemporary Cabin on Mt Ascutney

Windsor, VT

Free Wi-Fi

$419+

Check availability

Meadow View- 35 Acres outside your door

Windsor, VT

Pet friendly

$268+

Check availability

Sunset Cabin - your private romantic hideaway

Windsor, VT

10Wonderful(28)

Free Wi-Fi

Pet friendly

$224+

Check availability

Vermont cabin on 20 acres in open field

Windsor, VT

$246+

Check availability

Beautiful home offering privacy on 7 acres with private pond

Windsor, VT

Free Wi-Fi

Pet friendly

$484+

Check availability

Private wing of the Largest Colonial Revival Mansion in the US

Windsor, VT

$4,069+

Check availability

Stunning Modern Cabin on Beautiful Vermont Farm

Windsor, VT

Pet friendly

$464+

Check availability

Spacious Cabin Rental for a Farm Getaway in Windsor County, Vermont

Windsor, VT

Pet friendly

$325+

Check availability

Long Range Mountain Views in West Windsor

Windsor, VT

$586+

Check availability

Green Mountains

Windsor, VT

Pet friendly

$304+

Check availability

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Low season	February
High season	October
Average price (weeknight)	$342

Cheapest month to stay with an average 38% drop in price.

Most expensive month to stay with an average 45% rise in price.

Average Sun - Thu price over the last 2 weeks.

The best vacation rental properties in Windsor are Sunset Cabin - your private romantic hideaway (10.0, 28 reviews), Meadow View- 35 Acres outside your door (9.9, 42) and Meadow View- 35 Acres outside your door (9.9, 42), based on ratings and reviews from real travelers.
If you’re looking for a cheap vacation rental in Windsor, you should consider visiting during the low season. The cheapest vacation homes in Windsor can be found in February and June.
The cheapest night for renting a vacation home in Windsor is Thursday. In contrast, the most expensive is Tuesday.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Windsor for 2 days.

See more tips

What types of vacation rentals are available in Windsor?
There are loads of different property types that you can make your vacation home in Windsor. You’ll find cabins, cottages and villas.
Are there any pet-friendly vacation rentals in Windsor?
There are a number of dog and pet-friendly Windsor vacation rentals, with around 38% allowing you to bring your pet along with you.
How can I find vacation rentals near me in Windsor?
Take a look at our vacation rentals map to find the best vacation rental homes near you.