Owner Direct Vacation
Rentals in Windsor
The Best Owner Direct Vacation Rentals in Windsor. Explore thousands of vacation home rentals, large cabins, and villas near Windsor
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Explore the Best Windsor Vacation Homes
Looking for the perfect place to stay in Windsor? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Windsor character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Windsor Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Windsor
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Popular Neighborhoods for Windsor Vacation Rentals
What are the best areas to stay in Windsor
Discover the top neighborhoods in Windsor and choose a place that suits your stay.
Friday Jan 23
Windsor, Vermont
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Windsor vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Windsor
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How to Reserve Your Windsor Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Windsor Vacation Rental FAQs
1. What are the top vacation rentals in Windsor?
There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor:
- Meadow View- 35 Acres outside your door
- Sunset Cabin - your private romantic hideaway
- Beautiful home offering privacy on 7 acres with private pond
- Snapdragon Inn
- Antique farmhouse with spectacular mountain view in a bucolic setting.
- Luxury Vermont Vacation Rental Private Hot Tub!
- Exquisite Log Home with views near Woodstock, Vermont
- Long Range Mountain Views in West Windsor
- Lovely Vermont Cabin on a quiet street
- Cozy Historic Hilltop Cottage with Mount Ascutney View
2. How many vacation rentals are available in Windsor?
Currently, the total number of properties listed in 2026 is over 22 in the Windsor area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windsor.