Okemo Trailside Condos

Compare 19 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.

Popular amenities for Okemo Trailside vacation rentals

Popular
Dog-friendly Hot tub Internet
Tannen Spitz
5 Bedroom | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

$235 avg / night
(excludes fees and taxes)
3.17 (36)
Okemo Trailside 36E
4 Bedroom | 3.5 Bath | Sleeps 8

Okemo Trailside 36E - Ludlow, VT

$425 avg / night
(excludes fees and taxes)
4.78 (9)
Okemo Trailside 8E
1 Bedroom | 1 Bath | Sleeps 6

Okemo Trailside 8E - Ludlow, VT

$132 avg / night
(excludes fees and taxes)
3.52 (63)
Wood Lantern
5 Bedroom | 4.5 Bath | Sleeps 12

Wood Lantern - Ludlow, VT

$514 avg / night
(excludes fees and taxes)
4.47 (40)
Sachem Slopeside - Okemo Trailside 21B
4 Bedroom | 2.5 Bath | Sleeps 8

Sachem Slopeside - Okemo Trailside 21B - Ludlow, VT

$594 avg / night
(excludes fees and taxes)
4.1 (20)

View 14 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

loved the well equipped kitchen and the location on Sachem Trail. Kids loved the hot tub, and the ping pong table. Loads of games puzzles cards etc for the guests. Spacious kitchen/dining area and living room.
Charles B. | Nov 2025
Perfect vintage ski house vibes!! House is exactly as described and just what we were looking for. We really enjoyed the fireplace and hot tub. Okemo is one of our favorite places and we all had a blast
Patricia C. | Oct 2025
location, house was clean and neat. We would definitely return.
Sage O. | Oct 2025
Okemo Trailside vacation rental FAQ

Yes. 18 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   |   Ludlow   |   Vermont
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