Okemo Trailside Condos

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Make Okemo Trailside your next getaway

Fresh powder, small-town charm, and new memories on the mountain are waiting for you at Okemo Trailside Condo rentals. There’s an adventure for everyone, from skiing or snowboarding, to enjoying the endless views of Vermont. Getaway to the great northeast.

Explore more vacation rental amenities in Okemo Trailside

Pool | Electric vehicle charger | Ski-in/ski-out | A/C | Fireplace | Washer/dryer | Balcony | Pack-N-Play | Ping-pong table | Premier

Okemo Trailside vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Okemo Trailside 37B
4 Bed | 2.5 Bath | Sleeps 12

Okemo Trailside 37B - Ludlow, VT

$592 avg / night
(excludes fees and taxes)
Okemo Trailside 8E
1 Bed | 1 Bath | Sleeps 6

Okemo Trailside 8E - Ludlow, VT

$173 avg / night
(excludes fees and taxes)
3.48 (64)
Okemo Trailside 36E
4 Bed | 3.5 Bath | Sleeps 8

Okemo Trailside 36E - Ludlow, VT

$550 avg / night
(excludes fees and taxes)
4.8 (10)
Okemo Trailside 6A
3 Bed | 2 Bath | Sleeps 10

Okemo Trailside 6A - Ludlow, VT

$415 avg / night
(excludes fees and taxes)
4.14 (29)
Tannen Spitz
5 Bed | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

$333 avg / night
(excludes fees and taxes)
3.21 (38)

View 15 more homes

Recent Okemo Trailside vacation rental reviews

This place was perfect for our family of four for the long weekend. Perfect ski in ski out to Sachem. It’s right at the end of the parking area. Comfortable and convenient. We’ll happily rent again.
Laura L. | Jan 2026
We just wrapped up a family stay at The Shred Shack and couldn’t have been happier. The house was comfortable, well set up, and exactly what you want for a ski weekend. The ski-on/ski-off access is legit—an easy walk right to the Sachem Trail, which made getting on and off the mountain with the family incredibly convenient. Everything was clean, welcoming, and thoughtfully laid out for relaxing after a full day on the slopes. It really felt like a home base rather than just a rental. If you’re looking for a stress-free Okemo stay with great access and a family-friendly vibe, this place delivers. We’d happily stay here again.
Greg K. | Jan 2026
The house was perfect for what we needed. It was clean, and very spacious. The things I would improve upon are: In the arrival instructions, be more specific about where the valve to turn on the water is. Be more specific about where the lever is to open and close the flu on the wood burning stove. Fortify the wifi, so its not so spotty There was no cable tv There was a pool table, but no ping pong like the pictures showed. I realize a few of those things are being nit picky, but still thought they should be mentioned.
brian s. | Jan 2026
Okemo Trailside Frequently Asked Questions

Yes. 19 of our Okemo Trailside vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Okemo Trailside vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Okemo Trailside team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Okemo Trailside, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning


Explore our Okemo Trailside Condos in Ludlow, VT

Ludlow, VT is postcard-perfect with its quaint downtown area and stunning foliage or snow-capped peaks with the change of season. There are plenty of hiking trails, small artisan farm tours, and coffee shops to peruse between trips up and down the slopes. Don’t forget a souvenir of Vermont’s famous maple syrup to enjoy when you get back home.

With Okemo Trailside Condos, you can find a home base that suits you best with ski-in/ski-out options and room for the whole family. The popular ski resort is known for its stunning views and winter thrills. When you’ve had your fill of adventure, come back to your cozy rental and savor resort-style amenities.

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