Okemo Trailside Condos

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USA > Vermont > Okemo Trailside

Make Okemo Trailside your next getaway—choose from 32 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 Bed | 1 Bath | Sleeps 6

Okemo Trailside 8E - Ludlow, VT

From $74
Okemo Trailside 52B
4 Bed | 2.5 Bath | Sleeps 10

Okemo Trailside 52B - Ludlow, VT

From $672
Okemo Trailside 22DL: Shred Shack 3D Tour
1 Bed | 1 Bath | Sleeps 6

Okemo Trailside 22DL: Shred Shack - Ludlow, VT

From $153
Mountain View Chalet
4 Bed | 4 Bath | Sleeps 13

Mountain View Chalet - Ludlow, VT

From $252
Okemo Trailside 19BL 3D Tour
1 Bed | 1 Bath | Sleeps 4

Okemo Trailside 19BL - Ludlow, VT

From $125

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Recent Okemo Trailside vacation rental reviews

Great place for a family ski trip. Walk up the driveway and take a RIGHT and you will see a little trail that brings you to SACHEM trail. Super convenient location. Excellent wood stove we used all the time. Comfortable / cozy house. Towels/sheets/toiletries included. Dishwashing supplies too. We spent 3 nights there. Downstairs area has a separate living room area with another fire place & 2 bedrooms (one with twin beds and one with full bed.) Main floor has kitchen/dining area/living area with 1 bedroom and bathroom (full bed.) Upstairs is cute -- 1 room with bunk bed & twin bed -- be careful, no railing on the top bunk. Other room has a full bed -- these 2 rooms share a bathroom upstairs. Not the most updated place, lots of boxes of stuff from the owners in public spaces, but certainly worked nicely for our 3 night family trip. Adequate parking. The hill is steep -- please use AWD car with good tires in the winter when staying here. We were not able to get a late checkout, that was disappointing and they did not let us keep our cars in the parking area after checkout, was told it was a liability for them. Aside from checking out during a beautiful snowstorm and having to move our cars out of their steep driveway, we did enjoy the stay and would recommend to others -- just be prepared that parking at Okemo main mountain is limited and crowded, sort of ruined that last day, unfortunately -- would be great if the rental agency could have allowed the cars to stay in the parking area until an hour before the next check in, something like that. We'd be happy to stay there again due to the excellent location and good amount of space for a nice family trip. Hope you enjoy your stay there too!
Tamar L. | Jan 2022
Nothing beats the ski in ski out
Scott E. | Jan 2022
We had a great weekend at Treetop Hideaway. The house was very close to Okemo, so it was easy to get back and forth from the mountain. Plenty of comfortable beds, hot tub and fireplace were perfect after a day of skiing. The house had not been cleaned when we arrived but the cleaning crew arrived shortly after us. Would 100% stay here again.
Katherine B. | Jan 2022

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.