SUNNYSIDE RENTALS
Freshly groomed corduroy on an Okemo trail at dawn, with the valley and hills beyond

Okemo Mountain · Ludlow, Vermont

The Sunny Side
of Okemo.

Four hand-kept homes in Ludlow and on the mountain, booked direct from the person who keeps them.

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VRBO Premier Host · 9.6/10 guest rating on our flagship home

A big manager runs four hundred doors from a call center. I run four, and I know which one sticks in a cold snap.

The portfolio

The Homes

Four vacation rentals at Okemo Mountain, each one cleaned, checked, and answered for by me. The trail marker on each card tells you how you reach the snow.

Trail key Village — walk to town, drive to the lifts Mountain — minutes from the base Ski-in/ski-out — click in at the door
Live listing Winterplace Building F at Okemo seen from the chairlift, surrounded by snow-covered trees
Ski-in · Ski-out

Okemo Retreat

Ski out the door to the A/B lift. Ski home for lunch.

Winterplace Building F, at the top of White Loop. A king room, a queen room, and a bunk room the kids claim on arrival. Renovated in 2025, with a wood-burning fireplace and firewood stocked by the HOA all season. The community keeps a heated indoor pool, hot tubs in ski season, and two reserved parking spaces.

3 BR · 2 BA · Sleeps 8 · Ski-in/ski-out

Check dates on VRBO Full property site →
Sample White clapboard house at dusk with warmly lit windows and snow on the ground
Village

The Village Foursquare

Walk to dinner in Ludlow village; the access road starts at the end of the street.

4 BR · 2.5 BA · Sleeps 10

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Sample Weathered timber chalet on a sunny snow-covered slope under a blue sky
Mountain

Sugarhouse Chalet

Weathered timber on a sunny ridge above town, with a wood stove and a long view.

3 BR · 2 BA · Sleeps 6

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Sample A-frame cabin glowing at twilight among snowy pine trees
Mountain

The A-Frame at Trailside

A restored 1960s A-frame in the pines near Trailside, bunk loft up the ladder.

2 BR · 1 BA · Sleeps 5

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For owners

Managed Like It’s Ours

If you own a home near Okemo and run it from two states away, this is what I take off your plate.

Listings & pricing

Honest photos, straight copy, and rates set by someone who watches the snow report, not a spreadsheet.

Guest vetting & messaging

I read every inquiry myself and answer guests directly, before, during, and after the stay.

Turnovers & linens

Cleaned, restocked, and inspected between every stay. I check the corners.

Midnight furnace calls

When the heat quits at 11 p.m. in January, guests call me. You hear about it in the morning.

Local trades on speed dial

Plumbers, electricians, plow drivers. People who pick up because they know me.

Owner reports you can read

What came in, what went out, what needs fixing. One page, plain English.

Talk to Aly about your home

About Aly

The Person
With the Keys

I live at Okemo year-round, which matters more than it sounds. I meet the plow driver, restock the firewood, and notice when a storm door stops latching before a guest does. VRBO named me a Premier Host, and the flagship home I manage there holds a 9.6 out of 10 rating across 16 reviews.

I keep the portfolio small on purpose. Four homes means I know each of them the way you know your own: which window sticks, where the sleds live, when the pool is quietest. Guests text me and get me, not a queue. Owners get the same number.

Guest reviews

Word From the Hill

The kids skied to the lift while we finished our coffee. Spotless when we arrived, warm all week.

— Alex P. · Okemo Retreat · Feb 2026

Comfortable, clean, and easy. Alyson answered every question quickly, even the small ones.

— Suzanne B. · Okemo Retreat · Feb 2024

Great location, and a real fireplace with the firewood already stocked. Communication with Alyson was effortless.

— Michael R. · Okemo Retreat · Dec 2025