Discover winter rentals Windsor - We found 82 exact matches
About Windsor Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Windsor perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Windsor. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Windsor and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Windsor Winter Rentals
What are the top rated Winter 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 Winter Rentals in Windsor:
- Beautiful VILLA SEAGULL in Silver Sands Beach Resortn3 bedroom 3.5 baths
- Simmerdown Villa is a spacious modern 4 bedroom house within a gated community
- Charming 1-bedroom apartment in Stonebrook Estates, Trelawny with WiFi, AC
- Luxury 8BR Villa, Pool, Butler & Free Meal
- The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive
- New Seaside Romantic Cottage With Optional Pool
- Villa on the Rock ~ Luxury vacation rental near beach with Roof top lounge area
- Villa Applebee – from Home to Yard @ Stonebrook Manor!
- Adehya the Villa
- Netflix smart TV in room
How much does it cost to rent a place to stay near Windsor in the wintertime?
The average cost for winter rentals in Windsor is $470 per night. Vacation Cottage has a wide list of great winter places to stay near Windsor that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Windsor that allow pets?
Yes, here are the top cottage/chalet rentals in Windsor that allow you to bring your pet or dog:
- Beautiful VILLA SEAGULL in Silver Sands Beach Resortn3 bedroom 3.5 baths
- Netflix smart TV in room
- The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive
- Simmerdown Villa is a spacious modern 4 bedroom house within a gated community
See all pet-friendly vacation rentals in Windsor on Vacation Cottage
Do you have any winter rentals in Windsor that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Windsor to find what works for you.
Are there winter accommodations in Windsor that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 82 private swimming pools or indoor pools accommodations near Windsor along with other great amenities.
Do any winter holiday rentals in Windsor have hot tubs?
About 82 holiday rentals in Windsor boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Windsor?
Yes, there are many luxury places to stay in Windsor for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Windsor with all the best amenities for your next trip.
