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.

Popular amenities for Okemo Trailside vacation rentals

Popular
Dog-friendly Hot tub Internet
Okemo Trailside 8E
1 Bedroom | 1 Bath | Sleeps 6

Okemo Trailside 8E - Ludlow, VT

$181 avg / night
3.64 (53)
Tannen Spitz
5 Bedroom | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

$429 avg / night
3.17 (23)
Wood Lantern
5 Bedroom | 4.5 Bath | Sleeps 12

Wood Lantern - Ludlow, VT

$845 avg / night
4.49 (35)
Okemo Trailside 19BL
1 Bedroom | 1 Bath | Sleeps 6

Okemo Trailside 19BL - Ludlow, VT

$311 avg / night
4.4 (10)
Okemo Trailside 5B
3 Bedroom | 2.5 Bath | Sleeps 16

Okemo Trailside 5B - Ludlow, VT

$705 avg / night
4.29 (17)

View 15 more homes

Browse 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

Recent Okemo Trailside guest reviews

Can't beat first tracks to then get first chair! Great weekend great spot.
greg b. | Dec 2024
Love it! Beautiful 2 level condo with everything we needed for a weekend on the mountain. Easy access to the trail, no need to drive to the base lodge!
Logan D. | Dec 2024
We had a wonderful stay at the “cabin”. Although it is so much more than a cabin. The rooms are all spacious, particularly the primary bedroom with vaulted ceiling. The kids loved the sleeping loft. Separate seating area in the lower level for them to get away from the grown-ups was ideal. Everything was clean, well-maintained and cozy. What a lovely home for a family gathering! So close to the ski trail just 3 houses in from the Sachem Trail. Ludlow has a cool downtown with great shops and restaurants. We also did the short drive to Buttermilk Falls and hiked around in the snow. It was awesome. Would 100% stay here again! We highly recommend this home!
KATY O. | Dec 2024
Okemo Trailside vacation rental FAQ

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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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.

Nearby destinations

Appalachian Mountains   |   March 2025 Partial Solar Eclipse   |   New England   |   Vermont Lakes Region   |   Okemo   |   Ludlow   |   Vermont
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