Family Owned, Family Friendly

Windward Vacation Rentals (a.k.a. Windward Real Estate Holdings LLC) was started by John & Angela Finlay. As the parents of three school-aged children, vacation rentals have been our go-to for a great family vacation (especially in a pandemic!) We love being able to vacation in a house where our family can spread out (not crowded in hotel rooms!) and enjoy the area around it. We are adventurers and explorers by nature and love to find new areas in the United States every year.

Even when exploring new areas, we still always find ourselves coming back to the Finger Lakes area in New York State. It is a year-round area – winter snow sports, spring and summer hikes, boating & swimming and the magnificent fall foliage to explore. On top of this, you have quaint, fun towns like Skaneateles to explore and the Finger Lakes wine trail. We decided in 2021 to take the plunge and purchase our first rental house in Owasco, New York to not only enjoy as a family but to open up to other families to build their own adventures in the Finger Lakes as well. We plan to expand our rental house options in the years to come so stay tuned!

We look forward to sharing all that the Finger Lakes area has to offer to families and friends who are looking for adventure and relaxation in gorgeous upstate New York.