Okemo Trailside Condos

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USA > Vermont > Okemo Trailside

Make Okemo Trailside your next getaway—choose from 27 great vacation rentals

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.

Okemo Trailside vacation rentals for every getaway

Dog-friendly Hot tub Internet
Tamarack 12: Archie’s at SouthFace
1 Bedroom | 1.5 Bath | Sleeps 6

Tamarack 12: Archie’s at SouthFace - Ludlow, VT

$246 avg / night
Trailside Road Getaway
4 Bedroom | 2 Bath | Sleeps 11

Trailside Road Getaway - Ludlow, VT

$173 avg / night
Treetop Hideaway
4 Bedroom | 3.5 Bath | Sleeps 12

Treetop Hideaway - Ludlow, VT

$1,000 avg / night
Trailside 19BU & 19BL
3 Bedroom | 3 Bath | Sleeps 13

Trailside 19BU & 19BL - Ludlow, VT

$786 avg / night
Okemo Trailside 6A
3 Bedroom | 2 Bath | Sleeps 10

Okemo Trailside 6A - Ludlow, VT

$262 avg / night

View 22 more homes

Recent Okemo Trailside vacation rental reviews

Convenient location, steps to Sachem run. Clean, comfy, cozy, in great condition!!!
Phil R. | Mar 2023
Great location tucked back in the woods on the mountain with snow all around. Very clean inside. Just what we needed for a ski vacation!
Brandon H. | Mar 2023
Close drive to the mountain, comfortable and clean.
Laura F. | Mar 2023
Okemo Trailside vacation rental FAQ

Yes. 27 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.