Okemo Trailside Condos

Compare 22 vacation rentals.
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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.

Browse more vacation rental amenities in Okemo Trailside

Pool | Electric vehicle charger | Ski-in/ski-out | A/C | Fireplace | Washer/dryer | Bikes | Golf on-site | Ping-pong table | Tennis court

Popular amenities for Okemo Trailside vacation rentals

Popular
Dog-friendly Hot tub Internet
Okemo Trailside 19BU
1 Bedroom | 2 Bath | Sleeps 7

Okemo Trailside 19BU - Ludlow, VT

$343 avg / night
(excludes fees and taxes)
4.91 (11)
Okemo Mountain Vista
3 Bedroom | 2.5 Bath | Sleeps 8

Okemo Mountain Vista - Ludlow, VT

$622 avg / night
(excludes fees and taxes)
4.71 (7)
Doc's Folly
4 Bedroom | 3 Bath | Sleeps 8

Doc's Folly - Ludlow, VT

$553 avg / night
(excludes fees and taxes)
4.52 (21)
Okemo Trailside 37B
4 Bedroom | 2.5 Bath | Sleeps 12

Okemo Trailside 37B - Ludlow, VT

$379 avg / night
(excludes fees and taxes)
4.5 (2)
Trailside 19BU & 19BL
3 Bedroom | 3 Bath | Sleeps 13

Trailside 19BU & 19BL - Ludlow, VT

$396 avg / night
(excludes fees and taxes)

View 17 more homes

Recent Okemo Trailside guest reviews

We had a lovely, quiet, comfortable stay in this lovely home. Really liked the privacy of three floors and the fact there were basically two living rooms. Slept very comfortably.
Collin U. | May 2026
Perfect ski in and out right off Sachem trail that fit our family of 5 great!!
Carly R. | Apr 2026
Great stay for ski vacation, ski/ski out is an amazing bonus (first time). As mentioned by others, when the sachem lift is closed the ski in is a bit more complex and not necessarily suit Le for beginner skiers. But can def ski out without an issue. Good communication, answered all my inquiries in a timely manner. Although fireplace is not listed in amenities. It is very evident on the photo and simply omitting it in the amenities is a formality. To improve transparency, it should be stated explicitly. Same for bed capacity as photos show more beds than allowed occupancy.
Danny C. | Apr 2026
Okemo Trailside vacation rental FAQ

Yes. 21 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Okemo Trailside, log in to Trip Manager to explore the 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   |   New England   |   Vermont Lakes Region   |   Okemo   |   Mount Holly   |   Ludlow   |   Vermont
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