Okemo Trailside Condos

Compare 31 vacation rentals. Enter your trip dates to get started.
USA > Vermont > Okemo Trailside

Make Okemo Trailside your next getaway—choose from 31 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
Okemo Trailside 8E 3D Tour
1 Bedroom | 1 Bath | Sleeps 6

Okemo Trailside 8E - Ludlow, VT

From $66
25 Trailside Road
4 Bedroom | 2 Bath | Sleeps 11

25 Trailside Road - Ludlow, VT

From $385
Happy Trailside 3D Tour
2 Bedroom | 3 Bath | Sleeps 8

Happy Trailside - Ludlow, VT

From $108
Tannen Spitz
5 Bedroom | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

From $149
Okemo Trailside 19BL
1 Bedroom | 1 Bath | Sleeps 2

Okemo Trailside 19BL - Ludlow, VT

From $115

View 26 more homes

Recent Okemo Trailside vacation rental reviews

Absolutely beautiful home. Pictures do not do it justice. We had a large group and there was plenty of room for everyone. We did have a difficult time getting there because it was actively snowing and the roads are extremely difficult in the snow. (Our group did not all have cars/drivers built for the snow). But it was so worth it! The hot tub was lovely, the home was impeccable, the beds were so comfortable. We would stay there again in a heartbeat.
Vanessa D. | Dec 2021
Everything was great and as expected.
Raqib A. | Dec 2021
I loved it all thanks
Michael R. | Oct 2021

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.