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Top Holiday Rentals in Windsor County

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

Solitude Village at Okemo
Solitude Village at Okemo

Converted Carriage Barn | The Carriage House Unit1
Converted Carriage Barn | The Carriage House Unit1

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Treehouse at Wise Pines- SoBo
Treehouse at Wise Pines- SoBo

Quechee Village Getaway | The Cottage on Main
Quechee Village Getaway | The Cottage on Main

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Top Windsor County Hotel Reviews

Align Inn Vermont
Find out more about Windsor County
Find out more about Windsor County
Everything you need to know about Windsor County holiday rentals
Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.
Windsor County holiday rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Windsor County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windsor County holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!
How to find incredible deals on Windsor County rentals
At Expedia, we put the best Windsor County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Windsor County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor County holiday.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.