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 | Ski-in/ski-out | A/C | Fireplace | Washer/dryer | Balcony | Pack-N-Play | Ping-pong table | Premier | Tennis court

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

$263 avg / night 3.64 (53)
Tannen Spitz
5 Bed | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

$657 avg / night 3.0 (21)
Wood Lantern
5 Bed | 4.5 Bath | Sleeps 12

Wood Lantern - Ludlow, VT

$1,218 avg / night 4.49 (35)
Okemo Trailside 19BL
1 Bed | 1 Bath | Sleeps 6

Okemo Trailside 19BL - Ludlow, VT

$544 avg / night 4.4 (10)
Okemo Trailside 5B
3 Bed | 2.5 Bath | Sleeps 16

Okemo Trailside 5B - Ludlow, VT

$940 avg / night 4.29 (17)

View 15 more homes

Recent Okemo Trailside vacation rental reviews

Beautiful weather, great golf, great hiking, phenomenal views from the slope and the reservoir.
Ellen C. | Oct 2024
I loved the quiet of the location. Very peaceful.
Donna H. | Oct 2024
Spacious Mountain Retreat is the secret gem in the Ludlow/Okemo area. The house is far nicer and significantly more spacious than the pictures on the website show. We have stayed there already twice and, of course, plan on coming back. There are a lot of small details attended to that make staying here so relaxing and enjoyable. All of the rooms are large and the bedrooms have high-quality beds and the house overall is very comfortable. Unlike other houses, the kitchen is not small and is very well-stocked. There is a large eating area, lots of bedrooms, three bathrooms, a great family room, additional downstairs sitting area, two balconies, outdoor firepit, and a state-of-the-art hot tub. By the way, we loved the large mudroom when you enter the house where you can leave your gear without tracking it through the house as well as the convenient covered carport where you can charge your car.
Yitzchak C. | Sep 2024
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
Easy check-in
Professional 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.

People also search for

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