Okemo Trailside Condos

Compare 20 vacation rentals.

USA > Vermont > Okemo Trailside

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 8E

1 Bed | 1 Bath | Sleeps 6

Okemo Trailside 8E - Ludlow, VT

$228 avg / night

5 Bed | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

$622 avg / night

Sachem Slopeside - Okemo Trailside 21B

4 Bed | 2.5 Bath | Sleeps 8

Sachem Slopeside - Okemo Trailside 21B - Ludlow, VT

$630 avg / night

5 Bed | 4.5 Bath | Sleeps 12

Wood Lantern - Ludlow, VT

$1,149 avg / night

Okemo Trailside 19BL

1 Bed | 1 Bath | Sleeps 6

Okemo Trailside 19BL - Ludlow, VT

$315 avg / night

View 15 more homes

Recent Okemo Trailside vacation rental reviews

The condo unit was great! Plenty of space for our mixed age group. Very clean. We wouldn’t have walked to the ski trail (that was def too far for us), but the shuttle was amazing. It came immediately and the driver was so friendly. The condo was difficult to find without the exact street address provided, but Vacasa customer service was ultimately able to help. Towels (hand towels/washcloths) were in short supply and we were missing a sheet for one of the beds, so that’s just something to be aware of that others might encounter. We made it work tho! It’s a bummer that the enormous jetted tub was out of order (altho there was no signage in the unit anywhere indicating that, so maybe this info on the listing is outdated? We weren’t going to risk trying it tho.) and the fireplace wasn’t able to be used, but I’m guessing those are both short term things that will be remedied in the future. The view from the condo is gorgeous. There wasn’t a usable ski closet (the one that was there was filled with skis and other winter equipment), so we kept our skis in our vehicles. Not ideal, but worked ok. Something to be aware of tho. Overall, our group loved it - with the cleanliness, layout of the rooms and shuttle service being perfect! We’ll def consider staying there again next time we visit!

Shannon C. | Mar 2025

Great place for a family vacation! Easy walk to sachem trail, even for early elementary school aged kids.

Christopher P. | Mar 2025

We stayed here for a ski weekend with a few adults and teenage kids. The house fit us all comfortably and there are many spaces to hang out. It is a good comfortable size and even with 12 people, we were not on top of each other. The house was clean. A few dish towels and more oven mitts could be of use, and if you're going with a bigger group, I suggest bringing plastic cups. Bath towels are provided, but they were a little small, so if that's an issue for you, bring your own. It's nice and close to Okemo and the center of town and we took a lunch trip to Killington. Wifi worked great, which was great for us non-skiers who had to work.

Jennifer D. | Mar 2025

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

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.

People also search for