Looking for the ideal vacation rental in Windsor? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.
Luxury, Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals
Exceptional
1 reviews
Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave
Exceptional
78 reviews
Private Pool, Skiing, Hot Tub, Guest Services, Air Conditioner, Internet, Accessibility
Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, Toys
Exceptional
69 reviews
Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay, Family, Ski resorts
Fabulous
2 reviews
Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave
Exceptional
84 reviews
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals
Exceptional
2 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
5 reviews
Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Ski resorts
Fabulous
1 reviews
Internet, Accessibility, Parking, Security/Safety, Guest Services, Air Conditioner, Sports/Activities
Exceptional
4 reviews
AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area
Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Arcade, Dryer, Fireplace, Free Parking, Internet, Kitchen, Microwave, No Smoking
Exceptional
2 reviews
AC, Arcade, Dryer, Fireplace, Free Parking, Internet, Kitchen, Microwave, No Smoking
Exceptional
17 reviews
AC, Arcade, Balcony, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet
Exceptional
15 reviews
AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer
Exceptional
1 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
1 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
3 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
1 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Windsor.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our vacation rentals stand out?
Every vacation rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best vacation rentals in Windsor are:
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
You can explore 48 verified vacation rentals in Windsor. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.
Vacation rental prices in Windsor vary depending on the season, property size, and location. Rates typically start from around $215 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.
Most vacation rentals in Windsor include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.
Yes, many vacation rentals in Windsor welcome pets. Currently, 25 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.
For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.
Vacation rentals in Windsor often include amenities such as Fireplace/Heating, Wellness Facilities, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.
You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.