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

$178 avg / night
3.62 (55)
Okemo Trailside 32C
3 Bedroom | 2.5 Bath | Sleeps 10

Okemo Trailside 32C - Ludlow, VT

$410 avg / night
4.94 (16)
Okemo Trailside 36E
4 Bedroom | 3.5 Bath | Sleeps 8

Okemo Trailside 36E - Ludlow, VT

$548 avg / night
5.0 (5)
Tannen Spitz
5 Bedroom | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

$468 avg / night
3.08 (26)
Okemo Trailside 6A
3 Bedroom | 2 Bath | Sleeps 10

Okemo Trailside 6A - Ludlow, VT

$327 avg / night
4.27 (22)

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

This house was open and beautiful. The rooms were spacious, but the living room and basement were perfect for hanging out together. We loved the fireplace upstairs and the hot tub. They had plenty of bathrooms too. It was so close to Okemo, but we chose to ride Stratton or Sugarbush since we had IKON pass, but we want to come back here once we switch back to EPIC. Great house. Our two toddlers loved it too. Recommend!
Jennifer I. | Jan 2025
Easy in and out and all around great, rung in the new year here... we will def come back to this house if the opportunity arrises
Nicholas M. | Jan 2025
The home had plenty of room for our family of five and my niece and nephew. It had all the amenities to cook meals, be entertained, sleep and be right next to the slopes for easy on/off access. We would certainly stay again and recommend to others! Thanks for sharing your home away from home!
James M. | Jan 2025
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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