I guess I am wondering if you have an east or west leaning? As far as East coast goes, you can also look at several New Hampshire towns like Lincoln, Plymouth, or North Conway. In Maine you could look at Sugarloaf. You can fly to Manchester NH and be a lot closer than Boston.

Vermont and New Hampshire have great summer climate with lots of gravel and great road riding. Also clean clear lakes to swim in. Mountain biking venues are growing in number but there are many great systems to ride. The skiing is no where as forgiving as western skiing, but the east resorts are super crowded with people from Boston and NYC every weekend.

By the right place in Maine and if your goals are to cover your costs (fees/ taxes) versus an income property, I could help with a winter seasonal rental

I totally get your point. Renting has big advantages but I'm looking to move some retirement funds out of the stock market. It occurred to me a highly desirable vacation real estate investment would be a good hedge against a market collapse plus offer myself and my grown children a place to visit.

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Geoff from Indy
http://www.tlcendurance.com

He said in another post that his budget is $1 million. I don't think money is an issue for him

I have done similar to what you are thinking of doing in Park City. I rent out the winter, except for one week and spend time there in the summer and fall. In a few years at full retirement, plan on spending most of the summer and fall there. If you use a management company to rent they take a huge cut, July is also usually a very busy month, so if you don't use the place that entire month you can make some good money.

My thinking was like yours, as I had some extra money and did not want to put more in the stock market. I took some cash and refinanced my primary home at a lower interest rate, so my mortgage only increased by a few hundred. Even this year with drastically lower rentals I should be able to cover my carrying costs. If there is no ski season next year that will be a different story.

I only have a smaller condo, nowhere near the cost of $1,000,000. Do not know what size you are looking for or house vs condo but $1,000,000 will not get much of a house in Park City proper any more. For rental potential you want to be close to the ski resorts and town. Rather than a ski week vacation rental there is also potential to rent for the entire season.

It is terrible!! ;) DM me when you get to town! Let’s get outside!

To the OP, if you settle on Bend, I know a great agent in your house search!

Perhaps I'm looking in the wrong places (VRBO, AirBNB, HomeAway, etc.) and I'm relatively new at looking for summer rentals but it's been surprisingly hard to find that's reasonable. It seems that even if you're trying to do a 3 month rental they still want to charge a standard nightly rate so your monthly cost can be $5,000 - $7,500 per month for something in a ski town during the summer. I know that's significantly less than the cost of ownership but it really stings to write a check that large for a summer rental.

FYI as a skier I can tell you that a premium rental property will have direct ski slope access and all the bedrooms will have their own baths. Skiers are social animals and it's way more of a family affair than triathlon. Approach every possible purchase through the eyes of a bored doctor's wife who rather be shopping in town than braving a blizzard. That's where the money is.

ps: I prefer the blizzard and I married well so you won't see us in town too often!

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"They know f_ck-all over at Slowtwitch"
- Lionel Sanders

For long term rentals, at least in Park City, search the local newspaper or craigslist for ads near the end of the ski season for summer rentals and you would find monthly rentals much cheaper. You can also place an ad yourself looking for a rental. This way you are avoiding all the fees and commissions that VRBO and other sites charge.

I think it also affects the clientele - some groups may be less risk than others with higher rent.

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https://www.strava.com/...tes/zachary_mckinney

Park City or Breckenridge

If you're looking for a real estate investment, compare cap rates for the markets you're looking at (net of your own use, and the tax implications of that). If you don't know how or why to compare cap rates, don't pretend it's a real estate investment.

If you're looking for investment advice, this is probably not the best place. The fact that you're asking here suggests you're looking for vacation home advice.

You can create a retirement portfolio that will meet your needs without buying a glorified vacation home. My advice is to be honest with yourself about what you want.

There's nothing wrong with buying a vacation home that you've earned after years of hard work. If you want to do that, and it's within reason, you can and you should. But don't fool yourself into thinking it's an investment if it's not.

Great advice above. I'm 1.5 hours out of Truckee, CA and did the - Buy a condo at a ski slope, rent it out and then sell it to pay for college for the kid X years down the road.

Reality was:

1: the wife really likes going up on a whim and enjoys being there no matter the season.
2: it's nice to stash stuff there so a trip up is get food and go.
3: We did xmas for family almost every year for the last 18 years and that would have been prime rental time but we don't see family much.
4: My son grew up on ski team and is a way better skier than I am and more importantly enjoyed that phase of his life.
5: We never did rent it because we put stuff we liked in and #1
6: We never sold it for college money because 2008 knocked the price out. If we would have sold it before 2008 we would have gotten an insane profit but again, #1

So the reality didn't work out and it was tough during the depression or whatever they call that adjustment but life is like that.

Good luck in your decision.

I would sell it today and buy a motorhome but #1 is more important to me.

a couple of notes on this (we have several smaller properties in a few towns in Colorado fwiw)

Second home markets are usually the most volatile. In most ski towns here, ~$1M would be in that category but definitely anything less. Now how does "urban flight" play into this going forward? Hell if anyone knows but wherever you're looking, have your agent give you a glimpse of what happened leading up to 2008 and how long it took to recover from that. Lots of factors involved so that won't paint the full picture. If you're truly holding for the long-term this isn't a big issue.

Rental Management companies are typically 30%+ on fees they collect. Unless you live really close, be prepared to pay for fixing things that shouldn't break (patio doors, entry doors, deadbolts, washer/dryer... ...etc.) and replace stuff that people really don't care about like sheets, pillows, towels several times a year. At the moment, there's a huge labor shortage and handy people can pretty much name their prices. Want that toilet/shower fixed right away... $$$

Most towns have short-term rental taxes (total taxes in Breck are 12.75% and 11.5% in Steamboat (not 100% on this, going by memory)) in addition to all the other taxes and they have staff to scour the listing platforms and ticket those who don't have a business license.

I've found that smaller properties are considerably easier to keep filled than larger places and think slopeside properties are overrated. We put a higher priority on convenience (parking, proximity to town...). Sometimes those things are the same (say lower Ski Hill rd or 4 O'clock rd in Breck) but you'll most likely pay more for that (kinda duh but just want to make sure).

That all being said, these things can cash flow off ski season alone if that's an objective. All our places are on 15yr notes but we handle the bookings/filing and farm out the cleaning and handyman stuff

good luck and make sure to take the time to enjoy wherever you end up

So.....a few votes for Vermont. BUT here's my advice since I've lived in Vermont for decades including ski towns. Vermont is not the best option in my opinion for a second home. Property taxes are absurd and even higher for second homes. Real estate values were inflated before Covid19 due to low inventory and now it's insane. We have one of the lowest cases of infection rates and outsiders are flocking to Vermont. Houses that should really cost $500K around Stowe are close to 1 mill. Anything under $400K is a dive or serious fixer-upper at the moment. If you are very rich than maybe a Vermont ski town will work for you.

The VT roads are not as safe as they used to be. Certain counties are super dangerous to ride. We recently moved out to a very rural area of Vermont and I'm still not riding on the paved roads as people drive fast, give you little room and it only takes a second. The dirt roads are better and I only ride a mountain bike and my cross bike in the summer. My tri bike sits on the trainer permanently now. I have a triathlete friend who also lives in Vermont and claims she's been hit 7 times by cars. She's fearless. I guess I have a bit more self preservation built into my personality....but I'm digressing...

If I were to buy a second home near a ski area, I second Mont Tremblant. I have done IMLP and really liked the area as well. Both Mont Tremblant and IMLP give you access to amazing open water swimming, riding and running. MT also has a newer Olympic pool. You would always find like minded people to train with in the summer months.

Not all Vermonters are friendly. Many do not want outsiders buying up property and driving up real estate values even further. As it is many locals can't afford housing in Vermont anymore. Yes, outsiders bring in income, but it's a double edge sword. Many locals rely on-out-of state money but at the same time, do not like outsiders and look forward to when return home. There is definitely resentment towards the rich outsiders buying up property here.

Another tidbit - in Vermont you will suffer many different types of bugs and flies. This summer the deer flies were nuts. Worst anyone has seen in years. Yes it's pretty here but it's not the utopia described by others who don't live here all year round.

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Death is easy....peaceful. Life is harder.

 

Whistler Blackcomb BC, Canada

Probably stooooopid pricey but man I love Vancouver and the surrounding areas.

I just spend a few weeks vacationing in northern Michigan. Gorgeous -- great hiking, running and biking trails (and from what could tell, roads), plenty of OWS lake swims. "summer" there is June-Aug. Plenty of winter activities, although more in the x-country than downhill ski-ing. Traverse City and Grand Rapids Airports not too far. I loved it. Definitely worth looking into!

Bozeman is pretty nice, and real estate prices have been going up steadily as Bozeman has seen the biggest growth in people (not just per capita) in Montana the last several years. Back country skiing, ice-climbing etc are nice, but resort skiing a little less. Bridger Bowl is close by, but small, Big Sky is 1,5 driving (one-way) in winter, so I don't think you would rent it to many who want to ski in Big Sky.

Winter Park, Co

Mont tremblant, qc

Somewhere in the Silver Valley in ID. Couer d'Alene, Kellogg, places around there.

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