I'm a big ski fan and try to ski as much as I reasonably can out West during winter despite living on the East Coast away from the mountains.
I've spoken to a number of other ski enthusiasts and the math always leads to the same conclusion around ski home ownership. Financially, it doesn't make sense to own a second home for skiing vs simply renting. Assuming you have a full time job and the ski home is not within driving distance, you'll be lucky to use your ski home 3 or 4 weeks during the winter; you likely won't use it during the mud seasons and maybe you can get another couple weeks at the mountain home during the summer. Moreover, renting out your ski home will not cover the full annual cost of the mortgage and home maintenance, especially factoring in the cost of a management company that many hire to manage the rental process.
Instead of renting, I've purchased 16 weeks of timeshares so that, when I eventually retire in 10-15 years, I can ski all winter long while lodging in my ski-in/out timeshares. I currently own across multiple timeshare systems - Marriott, Hyatt, Westin, Marriott, and independent HOAs - so that I can experience and then improve my timeshare weeks ownership to suit my ski lodging preferences. Some of the weeks I own are fixed weeks 51/52/7 so that I don't have to worry about competing with other floating week owners for booking holiday week reservations. For my ski weeks that I don't use myself, I rent them out on Redweek, which covers my MFs and a bit more.
Due to COVID, I've been working from home since last March. This past fall, I decided that I would work through the winter at my ski timeshares for 4 months and try experiencing my retirement ski lodging plans 10 years earlier than I had planned. I originally purchased most of my winter timeshares in Park City (e.g. Marriott Summit Watch & Mountainside) but over the past several years, I've not been crazy about the ski terrain at PCMR so I used II to lock off my weeks and trade through II this winter, primarily to Breckenridge and Vail.
I know that there are II detractors out there, but I'm a fan. I agree that its not always easy to get what you want through II but its a reliable marketplace for trading timeshare weeks and it works. About half my exchanges were within flexchange and about half before. I was able to string together all my weeks Sat-Sat so that I didn't need to pay cash to book nights between checking out one week and checking in to the next week. The resorts that I stayed in were all ski-in/ski-out, with the exception of the month that I stayed at Marriott Evergreen and Douglas where it takes a 10 minute to shuttle ride to get to Vail. I purchased e-plus on all my initial exchanges so that I could upsize my units or to change resorts so that I could minimize moving rooms and buildings.
Everything worked out great. But there were a couple of improvement items to my winter living that I identified. First, I wasn't crazy about the need to take a shuttle to get to the mountain while staying at Marriott Evergreen and Douglas. While not a hardship, I'm seeking easy convenience and even a little bit of luxury. To rectify this, I am working on enrolling my resale weeks by purchasing DC points so that I can book at the Ritz at Vail Village. Second, even though I liked all the resorts that I exchanged into, the longest consecutive stay in a single room that I could arrange was only 2 weeks. While it was only a 5 to 10 minute walk or uber ride to the next villa that I was staying in, I'd rather avoid the need to switch rooms if I can. With DC points that I'm purchasing to enroll my resale weeks, I figure that I'll be able to string together II exchanges with DC point reservations so that I can get more consecutive weeks in a single room than I was able to manage via II alone.
I had a great winter experience and my ski timeshare ownership worked almost like I had planned. I'll continue to optimize my ski weeks ownership by buying and selling more weeks. With the 4 months of skiing this winter, my physical fitness is better today than its been for 6 years. I've lost weight, I'm healthier, and I'm more pain free in my knees and back due to my increased strength from all the physical activity. Its truly been a fantastic experience.
The ski-in/out convenience of the timeshare villas that I stayed in was great as well. Purchasing all my timeshare weeks was not insignificant in terms of cost but a comparable ski condo would have been well over a million dollars and I have far more flexibility with my timeshares due to II. So this winter has only reinforced that I'm on the right track with my timeshare ownership and my eventual retirement plans.
I've spoken to a number of other ski enthusiasts and the math always leads to the same conclusion around ski home ownership. Financially, it doesn't make sense to own a second home for skiing vs simply renting. Assuming you have a full time job and the ski home is not within driving distance, you'll be lucky to use your ski home 3 or 4 weeks during the winter; you likely won't use it during the mud seasons and maybe you can get another couple weeks at the mountain home during the summer. Moreover, renting out your ski home will not cover the full annual cost of the mortgage and home maintenance, especially factoring in the cost of a management company that many hire to manage the rental process.
Instead of renting, I've purchased 16 weeks of timeshares so that, when I eventually retire in 10-15 years, I can ski all winter long while lodging in my ski-in/out timeshares. I currently own across multiple timeshare systems - Marriott, Hyatt, Westin, Marriott, and independent HOAs - so that I can experience and then improve my timeshare weeks ownership to suit my ski lodging preferences. Some of the weeks I own are fixed weeks 51/52/7 so that I don't have to worry about competing with other floating week owners for booking holiday week reservations. For my ski weeks that I don't use myself, I rent them out on Redweek, which covers my MFs and a bit more.
Due to COVID, I've been working from home since last March. This past fall, I decided that I would work through the winter at my ski timeshares for 4 months and try experiencing my retirement ski lodging plans 10 years earlier than I had planned. I originally purchased most of my winter timeshares in Park City (e.g. Marriott Summit Watch & Mountainside) but over the past several years, I've not been crazy about the ski terrain at PCMR so I used II to lock off my weeks and trade through II this winter, primarily to Breckenridge and Vail.
I know that there are II detractors out there, but I'm a fan. I agree that its not always easy to get what you want through II but its a reliable marketplace for trading timeshare weeks and it works. About half my exchanges were within flexchange and about half before. I was able to string together all my weeks Sat-Sat so that I didn't need to pay cash to book nights between checking out one week and checking in to the next week. The resorts that I stayed in were all ski-in/ski-out, with the exception of the month that I stayed at Marriott Evergreen and Douglas where it takes a 10 minute to shuttle ride to get to Vail. I purchased e-plus on all my initial exchanges so that I could upsize my units or to change resorts so that I could minimize moving rooms and buildings.
Everything worked out great. But there were a couple of improvement items to my winter living that I identified. First, I wasn't crazy about the need to take a shuttle to get to the mountain while staying at Marriott Evergreen and Douglas. While not a hardship, I'm seeking easy convenience and even a little bit of luxury. To rectify this, I am working on enrolling my resale weeks by purchasing DC points so that I can book at the Ritz at Vail Village. Second, even though I liked all the resorts that I exchanged into, the longest consecutive stay in a single room that I could arrange was only 2 weeks. While it was only a 5 to 10 minute walk or uber ride to the next villa that I was staying in, I'd rather avoid the need to switch rooms if I can. With DC points that I'm purchasing to enroll my resale weeks, I figure that I'll be able to string together II exchanges with DC point reservations so that I can get more consecutive weeks in a single room than I was able to manage via II alone.
I had a great winter experience and my ski timeshare ownership worked almost like I had planned. I'll continue to optimize my ski weeks ownership by buying and selling more weeks. With the 4 months of skiing this winter, my physical fitness is better today than its been for 6 years. I've lost weight, I'm healthier, and I'm more pain free in my knees and back due to my increased strength from all the physical activity. Its truly been a fantastic experience.
The ski-in/out convenience of the timeshare villas that I stayed in was great as well. Purchasing all my timeshare weeks was not insignificant in terms of cost but a comparable ski condo would have been well over a million dollars and I have far more flexibility with my timeshares due to II. So this winter has only reinforced that I'm on the right track with my timeshare ownership and my eventual retirement plans.
Last edited: