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

$432 avg / night
(excludes fees and taxes)
4.5 (2)
Okemo Trailside 8E
1 Bed | 1 Bath | Sleeps 6

Okemo Trailside 8E - Ludlow, VT

$158 avg / night
(excludes fees and taxes)
3.49 (67)
Okemo Trailside 6A
3 Bed | 2 Bath | Sleeps 10

Okemo Trailside 6A - Ludlow, VT

$375 avg / night
(excludes fees and taxes)
4.06 (31)
Tannen Spitz
5 Bed | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

$352 avg / night
(excludes fees and taxes)
3.2 (41)
Okemo Trailside 36E
4 Bed | 3.5 Bath | Sleeps 8

Okemo Trailside 36E - Ludlow, VT

$513 avg / night
(excludes fees and taxes)
4.82 (11)

View 15 more homes

Recent Okemo Trailside vacation rental reviews

Great ski in ski out home. Your back yard is a fun green slope to the main base area. Best ski in/out I’ve done. To address some other reviews, we were never cold on the main floor, there was plenty of wood, though we didn’t use it. There is a microwave now and parking is some of the easiest I’ve had for a location like this, with up to three spaces. The kitchen was very nice, and main living space all together was excellent. One suggestion would be to reconsider having two bunk rooms and instead put another queen/king space together, but I’m sure the owners have their reasons. Hot tub worked. Showers were great pressure and hot. I’d stay here again in a minute, my only reservation would be the limited adult sleeping space, we usually travel with couples.
Troy S. | Mar 2026
Great space that can accomodate multi-generational travel/skiing!
Timothy M. | Mar 2026
Great location. Kitchen needs obstructive cabinets removed but otherwise a cute and convenient place.
Michael G. | Mar 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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